Showing posts with label Daniel Waugh. Show all posts
Showing posts with label Daniel Waugh. Show all posts

11 January 2020

Mysterious St. Louis mob figure brutally murdered in Detroit

One hundred years ago tonight, a mysterious St. Louis underworld figure was found brutalized and near-death just outside of the southwestern edge of Detroit. The man was able to speak briefly with police and claimed that his name was Angelo Russo and that he had recently come to the Motor City. A century later, the man's true identity and the reasons for his violent death are uncertain. The following is an excerpt from my 2019 book Vìnnitta: The Birth of the Detroit Mafia.


Sometime around 1:30 on the morning of January 12, 1920, an anonymous Detroit police patrolman was walking his beat along Michigan Avenue just west of downtown. On this cold winter’s night, the streets were nearly empty, so the officer’s duty mostly consisted of staying warm and keeping his eyes and ears open. The officer noticed a westbound sedan headed towards him and in the direction of the Southwest Side. The vehicle caught his attention because of a burnt out headlight and the loud bursts of singing emanating from its interior. The words were in Sicilian, which the officer did not understand, but he thought it sounded nice as he idly watched the car pass by and disappear down the avenue. It was only later that this officer learned that the loud singing he had heard in the car was drowning out the strained sounds of a man being murdered within. 

Almost an hour later, John Stricki (or Striettzki) and his wife were awakened inside their home on Southern Avenue by a loud banging on their front door. As Stricki listened in, a Sicilian man pled in broken English for him to open the door. When Stricki refused, the caller swayed to the right (knocking over an oil lamp as he did so) and broke one of the front windows. The noise fully roused Stricki’s wife and five children, but a look through the broken window showed that the caller was no threat. The man was covered in blood and now lying on the front lawn, moaning in pain. As his ill wife cared for the wounded man, Stricki left to summon the police.

At Receiving Hospital, doctors took stock of the victim’s gruesome condition. Defensive wounds on the arms and wrists indicted that the dying man had fought fiercely for his life, and had received over forty stab wounds all over his torso in the process. During this frenzied attack, the victim had also been beaten about the head with a hammer hard enough to fracture his skull. The man had then been shot in the abdomen, neck, and a third time straight through his mouth. As if all that wasn’t enough, the victim was found to have an older, partially healed bullet wound in his back. Despite his tremendous injuries, the still-unidentified victim was not only still alive but willing to talk. Black Hand Squad head Inspector William Good and Assistant Wayne County Prosecutor Robert Speed quickly got to his bedside to take a statement.

Although his mouth wound made speech difficult, the wounded man managed to say that his name was Angelo Russo, that he was thirty-two years old, and had recently arrived in town from St. Louis. Russo said he was currently rooming at 51 Trumbull Avenue. The wounded man claimed he had been shot in the back by three men in front of 460 E. Fort Street on New Year’s Eve night. The wound was minor enough for him to leave the hospital just a few hours after it was inflicted.

Earlier on this particular evening, Russo was at Salvatore Randazzo’s poolroom at 152 St. Aubin Street in the company of five men, all of whom he apparently named to Inspector Good and Prosecutor Speed. They eventually left in a sedan with a burnt-out headlight to grab a bite to eat at an all-night restaurant downtown. The party then headed west on Michigan Avenue; it was at this point that the horrific attack began. Russo was dumped out of the car on Southern Avenue between Cabot and Miller roads; about 180 feet outside of what were then Detroit’s southwestern city limits. Somehow able to keep his feet despite his wounds, the bloodied Russo staggered over a block away until he stumbled up to John Stricki’s front door. Roughly two hours after giving this statement to police, the victim died from his injuries. 

Santo Pirrone was questioned in the murder of Angelo Russo.
Acting on information gleaned from the dying man, police arrested twenty-five year old mafiùsu Santo Pirrone at his home at 779 McDougall Avenue.  Also taken into custody was a young woman that Pirrone identified as his wife. Russo’s statement was bolstered by the recovery of Pirrone’s blood-stained automobile on West Jefferson Avenue around the same time. A key member of Peter Mirabile’s Alcamesi dicìna, Pirrone was noted as a longtime friend (and eventual brother-in-law) of Salvatore Catalanotti, who had taken on a much bigger role in the affairs of the burgàta upon the ascension of John Vitale to càpu. Pirrone admitted being with the victim on the night of the murder and even conceded to driving him to the Southwest Side, but only to drop off his “wife” at the home of her father on Cabot Road, not far where Russo was dumped from the car. Pirrone claimed to have absolutely no idea that the brutal attack was taking place right behind him in the back seat.

Despite his implausible claims and the fact that he admitted driving the murder vehicle, Santo Pirrone managed to beat the rap. Angelo Russo’s body lay unclaimed for nearly two weeks until it was interred in a pauper’s grave at Woodmere Cemetery at city government expense. The ferocity of the attack earned Pirrone the underworld nickname of U Bistìnu (The Shark). Just who Russo really was, as well as what he was doing in Detroit and why he would be killed in such a grisly manner are questions that have never been satisfactorily answered. It is possible that new càpu Vitale, hypervigilant against threats, came to believe that Russo was a hired gunman brought in from St. Louis to kill him. Whether this was true or not, it is a likely motive behind the killing.

Postscript

The author was unable to find any solid record in St. Louis or elsewhere of Angelo Russo and has doubts that this was the man's true name. Just who he was and why he was killed are mysteries that may never be solved.

Angelo Russo's death certificate

Santo Pirrone eventually anglicized his name to Sam Perrone and made a fortune in the bootlegging business while a member of the Detroit Mafia. In later years, Perrone would move into the scrap business and become a noted union buster. Perrone was later charged with leading an unsuccessful attempt to assassinate UAW President Walter Reuther in the spring of 1948. By the early 1960s, Sam Perrone had begun feuding with mobster Anthony "Tony Jack" Giacalone, who got permission from the family's bosses to kill his rival. Perrone survived a subsequent car bombing, though he lost his left leg to the blast. After this incident, the contract on Perrone's life was cancelled with his retirement. Perrone died of natural causes on Christmas Day, 1973, his seventy-eighth birthday.

Sources

Waugh, Daniel. Vìnnitta: The Birth of the Detroit Mafia. Lulu Publication Services, 2019.

Detroit Free Press, January 12, 1920.

Detroit News, January 12, 1920.

Michigan Department of Heath, Certificate of Death, No. 1126, 1920.

Sam Perrone article on gangsterreport.com

05 December 2019

Chicago Gangster Hazed By Frat Brothers

James Clark is familiar to most crime buffs as a member of Chicago's North Side Gang during Prohibition. A capable, all-purpose muscleman and assassin, Clark joined the North Siders in the early 1920s. He acted as a pallbearer at the November 1924 funeral of his boss Dean O'Banion and was suspected by Chicago police of being one of the killers (along with Frank and Pete Gusenberg) of Pasquale Lo Lordo, càpu of Chicago's traditional Sicilian Mafia burgàta and president of the Italo-American National Union (formerly known as Unione Siciliana).

Chicago gangster James Clark

However, Clark is probably best known for being slaughtered in the St. Valentine's Day Massacre in 1929, when he and six of his colleagues were lined up against the north wall of the S.M.C. Cartage garage at 2122 North Clark Street and mowed down by hitmen masquerading as police officers. Most people do not know that nineteen years before Clark got his fatal love letter from a pair of Thompson submachine guns, he botched a burglary at a University of Chicago fraternity house and got a whole lot more than he bargained for in the process. The details of Clark's bungled crime are darkly funny, as if they were ripped from the pages of the script for Animal House.

Albert Rudolph Kachellek was born in Krojanke, Germany (present-day Krajenka, Poland) on February 25, 1889, and landed in America with his mother Anna and siblings a month after his fourth birthday. While growing up in Chicago, he quickly fell in with the wrong crowd. By the age of sixteen in 1905, he did a four-month jail sentence in the Bridewell for robbery. That same year, he also drew a four-year sentence for burglary. By this point, Kachellek started calling himself "James Clark"; his sister stated that "he did not want to hurt my mother's feelings." While he was destined to eventually become a professional gangster, James Clark in the winter of 1910 was a twenty-one-year-old ex-convict who was firmly planted at the bottom of Chicago's criminal totem pole. Clark began setting his sights on houses in the affluent South Side neighborhood of Hyde Park which bracketed the University of Chicago. A few of the stately homes in the district acted as rooming houses for fraternities at the nearby college. For a tough skel who had done hard time at Joliet, surely those college kids would be easy marks.


Alpha Tau Omega was established at the Virginia Military Institute on September 11, 1865 by Otis Allan Glazebrook, Erskine Mayo Ross, and Alfred Marshall as a means of using Christian brotherly love as a way of fostering reconciliation after the Civil War. The fraternity is noted for holding several retreats and training conferences; Altitude, Encounter, Valiant, President's Retreat, and Emerging Leader's Conference. All had specific goals; Altitude was meant to challenge members physically, mentally, and emotionally and currently entails a rigorous hike into the Rocky Mountains and the attainment of a 14,000 foot summit; Valiant puts roughly 100 members through a values-based curriculum that emphasizes effective leadership, communication, ethics, goal setting, and teamwork.

By the winter of 1909-10, Alpha Tau Omega had over one hundred chapters all over the United States and outside many major universities. The University of Chicago's chapter featured about twenty young men from such diverse states as Iowa, Indiana, Ohio, North Dakota, Texas and Louisiana. Most of the young students who were members of the fraternity lived in a house at 923 East Sixtieth Street that fronted Midway Plaisance Park. It was a quiet residence in a generally quiet neighborhood that houses one of the best colleges in the state of Illinois. It was towards this house that James Clark went in the early morning hours of March 6, 1910.

Although it was still technically winter in Chicago, the weather was quite mild and a harbinger of the coming spring; the temperature peaked at sixty-three degrees earlier that afternoon. Around five-thirty on that Sunday morning, Clark approached Alpha Tau Omega frat house on Sixtieth Street. Standing outside the dark and silent building, and with no one to be seen or heard in the pre-dawn stillness, Clark jimmied open a downstairs window. Whether Clark acted on impulse or pre-planned the burglary is unknown; the former seems likely, as he brought nothing to hold his loot. Once inside the quiet frat house, Clark moved with the noiseless stealth of the long-term burglar.

As the Alpha Tau continued their slumber, Clark's nimble fingers pocketed an array of loot such as brushes, neckties, change purses, gloves, spectacles, a knife, fountain pen, and an open-faced gold watch. With his pockets crammed to capacity, Clark reached for a packet of love letters tied with a maroon ribbon. Just as he was putting the letters in his jacket, Clark's heart leaped up into his throat at the unexpected sound of an angry voice asking him just what he was doing. The voice belonged to Henry Brown, the "porter" of the frat house. The sight and sound of the frightened, muscular Black man seemed to have caused Clark to freeze. In the blink of an eye, Brown struck Clark with a stick and quickly went away to find a gun.

On the third floor of the house, pajama-clad frat brothers were aroused by the commotion and began spilling from their beds. Loud footsteps and numerous voices bombarded the concussed Clark, who despite his befuddlement at the sudden wrong turn the evening's burglary had taken had enough presence of mind to make way. Clark managed to hop right out the window that he had originally entered no more than fifteen minutes earlier. The fleeing thief found his legs and sprinted across the street and down Midway Plaisance with porter Henry Brown hot on his heels.

The roused Alpha Tau frat brothers saw the beginning of the chase and promptly burst out the front door of the frat house and joined Brown in persuing the suspect. While James Clark was in reasonable shape, he wasn't exactly a track-and-field star, and Brown and the Alpha Tau brothers ran him down in the park, about a block and a half away from the house. Clark was pinned into the grass and pummeled with curses, fists, feet, and general righteous indignation. And the Alpha Tau were just getting started.

The frat brothers hauled the dazed and bleeding Clark to his feet, and with Brown marched him back to the house. The adrenalized youths began singing their college songs loud enough to wake residents of the surrounding homes. Once they reached the stone steps of their frat house, the youths punctuated their songs with a unison bellow of "CHICAGO!" They then proceeded to haul their prize catch up the steps and into the house. Said prize catch was probably wondering by this point just what the hell he had gotten himself into.

Exactly what the Alpha Tau brothers did to James Clark in the frat house may never be known. An anonymous Chicago Tribune scribe, tongue planted firmly in cheek, wrote, "…did they place Mr. Burglar in a large leather chair? No. On second thought, they took Mr. Burglar upstairs and put him in the bathtub. They gave the treatment usually accorded unwilling and recalcitrant freshmen. They then called up a doctor to 'fix up' Mr. Burglar. Lastly, they called the police."

At six-thirty that morning, Lieutenant John L. Hogan and Officers Curtin and Loey arrived at 923 Sixtieth Street from the Woodlawn Station. According to the same Tribune reporter their arrival, "saved Mr. Burglar from further punishment à la college." James Clark was booked for burglary while eight of the frat brothers donned buttoned-up sweaters and Dutch trousers to come down to the Woodlawn station in order to identify some of their property if they could. Louis T. Curry claimed a knife and a muffler; Dwight Hill a watch and a change purse; J.M. Sutherland of Marlin, Texas a $5 watch and fifty cents in change; M.E. Seeley from Ohio reclaimed two pairs of eyeglasses while D.T. Long of Indiana claimed his $30 watch and two neckties.

Suddenly the mood turned sour when Lieutenant Hogan decided to hold all the stolen property as evidence against Clark. Young Seeley protested, "…if you don't give me back those glasses, I'll have a deuce of a time. One pair is for reading and the other is for seeing where I'm going. If you don't give 'em back to me, I won't be able to study or find my way back to the frat house." Seeley's pleas went for naught. The only piece of property that the lieutenant failed to get his hands on was the packet of love letters tied with the ribbon. They had mysteriously disappeared in the commotion of the hazing and arrest. The youths pointedly declined to reveal which one of them had written the letters.

James Clark was eventually convicted of burglary and, because this was his so-called "third strike," was sentenced to a term of one year to life in the state prison at Joliet. Clark would not be paroled until 1914.

Six of the seven victims of the St. Valentine's Day Massacre. Lying perpendicular at the base of the wall is James Clark.
History does not record what became of Henry Brown and the rest of the Alpha Tau Omega frat brothers who made Clark's life a living hell during a burglary gone wrong in the winter of 1910.

Sources:

Chicago Tribune, March 7, 1910.

Keefe, Rose. The Man Who Got Away: The Bugs Moran Story. Nashville, Cumberland House, 2005.

World War I Selective Service Draft Card, Albert Kachellek.

Ellis Island passenger arrivals, 1893.


02 October 2019

The Assassination of Sam Giannola

Detroit Mafia boss Sam Giannola

One hundred years ago today, Detroit Mafia boss Salvatore (Sam) Giannola was assassinated as he stepped from the American State Bank branch at the corner of Monroe and Russell streets in Detroit, Michigan. Giannola and his two brothers, Vito and Antonino (Tony), were natives of Terrasini, Sicily and had led the city's Mafia family since the spring of 1914, when they seized control of the burgàta after winning a gang war against incumbent boss Pietro Mirabile. 

Based in the southern Detroit suburb of Ford City, the Giannolas had gained untold wealth and power from their newfound positions at the head of the city's Mafia family. Unfortunately, they had also accumulated a host of enemies both inside and outside of their organization. Sam's brother Tony had been murdered in January 1919 and Sam led his faction in a blood feud against his enemies, a faction headed by Giovanni (John) Vitale. After a peace treaty had been enacted in late May, things seemed to have calmed on the surface, but the bad blood between Giannola and Vitale seemed set to erupt at any time.

On October 2, 1919, Sam spent a good chunk of the day at his Little Sicily headquarters, the Viviano Macaroni Manufacturing Company, at 277 Monroe Street. Around 2 o'clock that afternoon. Giannola went to the American State Bank to cash a $200 check (Sam was looking to place a bet on the upcoming Game 2 of the ongoing baseball World Series). After finishing his business, Giannola was confronted by three assassins who shot him multiple times. Sam staggered back inside the bank and collapsed to the floor, quickly dying of his wounds. His three assassins ran in opposite directions on Russell Street. Sam's funeral in Wyandotte four days later was a elegant and well-attended affair. His widow Rosa swore an oath of vengeance against his killers at his gravesite.

Detroit Free Press


One of Sam Giannola's accused killers, Calogero Arena, was actually found guilty of the crime in March 1920 and sentenced to life imprisonment. However, Arena's conviction was reversed on appeal, and he was acquitted at his second trial.

If you'd like to read more about Sam Giannola's life and career, I invite you to check out my book Vìnnitta: The Birth of the Detroit Mafia


Sources:

The October 3-6, 1919 issues of the Detroit Free Press, Detroit News, and Detroit Times

Sam Giannola, Michigan Department of Health, Certificate of Death, No. 9756 (1919).

Recorder's Court of the City of Detroit, The People of the State of Michigan vs. Cologero Arena for murder, 1919, Case # 30216.

Daniel Waugh. Vìnnitta: The Birth of the Detroit Mafia. Lulu Publishing Services, 2019. ISBN 9781483496276.


20 September 2019

The Mother Of All Drive-By Shootings


Al Capone (left) and his bodyguard Frank Rio.

On this day ninety-three years ago, members of Chicago's North Side Gang led an extraordinarily violent raid against their archrival Al Capone near his headquarters in the suburb of Cicero, Illinois. A procession of automobiles raked an entire city block with submachine gun fire to avenge the murder of their boss, Dean O'Banion, two years earlier. This attack was unlike anything seen in the American underworld at the time, and it has become one of the canonical stories of Al Capone's rise to power. Many myths have sprung around it over the years, namely around the number of vehicles involved and Capone's bodyguard Frank Rio saving his boss from certain death at the hands of his enemies. It was a scene tailor-made for the silver screen, where it would indeed end up just six years later. The purpose of this article is to give the various accounts of the Hawthorne attack a fresh examination and create an accurate depiction of this seminal event.

Background

By the summer of 1926, twenty-seven-year-old Alphonse Capone had been at the head of an ever-expanding vice empire that raked in multiple millions of dollars from the manufacturing, smuggling, and sale of illegal alcohol for over a year. Other rackets that fed Capone's coffers included illegal gambling, labor racketeering, prostitution, and protection racketeering. Due to the election of reform mayor William Dever in 1923, Capone headquartered his mob just across the Chicago city line in Cicero. Al and his crew installed themselves at the three-story Hawthorne Hotel at 4823 West Twenty-Second Street (modern-day Cermak Road). The gangsters commandeered the entire third floor for their use; Capone installed solid steel shutters on the windows as a security measure. Al was right to take such precautions as he had plenty of rivals who were eager to see him dead. Capone's former boss, Johnny Torrio, had been shot and nearly killed in January 1925 by North Side gangsters Hymie Weiss and Bugs Moran, both of whom were eager to avenge the assassination of their friend and leader Dean O'Banion two months earlier.

Earlier in the spring of 1926, Capone had begun a brief move against a West Side gang headed by the O'Donnell brothers. One foray against them on the evening of April 27 resulted in gangsters Jim Doherty and Thomas "Red" Duffy being shot to death outside of the Pony Inn on Roosevelt Road (police later determined that Capone, eager to try out the newfangled Thompson submachine gun, personally did the shooting). Also killed in the assault was Assistant State's Attorney William H. McSwiggin, known around Chicago as the "hanging prosecutor." McSwiggin had merely gone out to have a few harmless drinks with his pals in the O'Donnell Gang when he found himself caught in the crossfire of gangland warfare. Capone was forced to lay low for a good chunk of the summer while the case against him was fixed. Despite the intense uproar over the killing, the Cicero gang boss not only managed to beat the rap but also to neutralize the threat that the O'Donnell mob posed to him.  


North Side Gang boss Earl "Hymie" Weiss



The so-called North Side Gang posed the greatest challenge to Al Capone in the summer of 1926. They controlled lucrative bootlegging and vice rackets on the city's North Side. After their previous leader, Dean O'Banion, was assassinated at the Schofield flower shop at 738 North State Street by men believed to have been sent by Johnny Torrio and Capone, the gang was taken over by Earl "Hymie" Weiss. Twenty-eight years old, Weiss was an intelligent, industrious gangster who had long been regarded as the "brains" behind the North Side mob; police believed that he was the one who had steered the crew into large-scale bootlegging. Weiss was noted for intensity that practically oozed from his pores and a hair-trigger temper. When photographers tried to snap his picture, he'd stare at them and say, "If you take a picture of me, I'll kill you." In one interview, Fred Weiss said he had seen his brother Earl only once in twenty years, "That was when he shot me, six years ago." According to his descendants, Weiss suffered from frequent migraine headaches, and in the mid-1920s was diagnosed with arterial cancer. These health ailments, along with the knowledge that he probably did not have long to live as a result, are said to have contributed to Weiss's fearlessness in the underworld. Despite his fearsome reputation, Weiss was known to secretly pick up the grocery tabs of less fortunate denizens of his North Side neighborhood.

Vincent "Schemer" Drucci

Backing up Hymie Weiss in the ranks of the North Side Gang was an equally colorful cast of characters. Vincent Drucci was a Sicilian-American gangster who got his nickname of "Schemer" because of his wild criminal schemes and madcap personality. While being chased by police through downtown Chicago in 1922 after trying to dynamite a safe, Drucci came upon the Michigan Avenue Bridge, which was raising to allow a river-going freighter to pass through. The Schemer's response was to floor his car's accelerator and gun his ride Bluesmobile-style up and over the bridge's increasing gap. Unfortunately for Drucci, the cops also managed to make the jump and caught up with him a couple of blocks later. Another top echelon member of the North Side Gang was George Moran, who was often incorrectly said to have been of either Irish or Polish extraction; he was, in fact, French-Canadian. Born Adelard Cunin in St. Paul, Minnesota, Moran was known as being a tough and shrewd criminal who had been moving in North Side gang circles since at least 1917, when the crew was primarily a safe-cracking outfit led by Charles "The Ox" Reiser. Due to his occasional fits of temper, Moran was nicknamed "Bugs."

George "Bugs" Moran
By the summer of 1926, Hymie Weiss had managed to forge an alliance with the South Side-based Soltis-McErlane mob. Their territory encompassed what is known as the New City area of the Southwest Side. As gang boss Joe Soltis explained to Chicago police captain John Stege, "My district extends from Thirty-Ninth to Fifty-[F]ifth sts., and from the city limits to Loomis st. And I'll kill any [expletive] who cut in on my business." A tough and often murderous saloonkeeper who had branched into bootlegging, Soltis was a fierce fighter who managed to generate immense profits while navigating the violent, rapidly shifting gangland ecosystem of Chicago's South Side. Soltis's partner was Frank McErlane, one of the most feared men in the entire city. An alcoholic psychopath who made even his own gang mates nervous, McErlane was credited with being the first Chicago gangster to use a Thompson submachine gun on his enemies in the late summer of 1925. Although McErlane was currently in Indiana fighting a murder charge, Joe Soltis secretly made a pact with Weiss to move in on Capone around mid-summer.


Prelude

On the warm summer day of Tuesday, August 3, thirteen-year-old John Novak was horseback riding with his eleven-year-old brother Joseph in a forest preserve in Palos Township in southwestern Cook County. In the early afternoon, with the temperature climbing, the Novak boys sought to water their horses at a cistern. When their mounts shied away from drinking, the brothers investigated and were shocked to find the body of a dead man submerged in the water. The corpse had been bound hand and foot before being weighted down with stones and bricks from a nearby house that had burned down months before. The deceased was soon identified as thirty-six-year-old Anthony Cirringione, aka Tommy Ross, known as Al Capone's chauffeur. Cirringione (his name is usually misspelled as Curingione or Cuiringione) had been abducted over a month earlier, while Capone was still in hiding over the McSwiggin case. The chauffeur had been beaten and tortured severely (one account says his corpse was covered with cigar and match burns) before his skull was crushed by a blunt instrument (some contemporary news accounts mistakenly say he was shot). What Cirringione's killers hoped to get out of him would not become clear for another month or so. While this murder is usually attributed to the North Side mob, the location of the killing (rural southwest Cook County) and the use of torture indicates that the Soltis-McErlane crew was at the very least involved, if not solely culpable, in the slaughter of Capone's driver.

Capone was convinced that one way or another, the North Siders were responsible for the murder of his friend, and thus began planning accordingly. On the morning of Tuesday, August 10, Hymie Weiss went to the Congress Hotel at 500 South Michigan Avenue to meet Vincent Drucci, who lived in a suite on one of the upper floors. After they finished breakfast around ten o'clock, both men began walking south on Michigan. At East Ninth Street, the gangsters crossed the street and headed towards the Standard Oil Building. The exact business of Weiss and Drucci that morning is still unclear to this day, but the latter had a total of $13,200 cash in his pocket, money that he would later claim was earmarked for a real estate deal. Police would later note that the Standard Oil Building contained the office of the Chicago Sanitary District, known as perhaps the most corrupt pork barrel in the entire city (an impressive feat in and of itself). At that moment Morris Eller, a Sanitary District trustee and alderman of the Twentieth Ward, was in the office talking with Assistant State's Attorney John Sbarbaro.

As the North Side gangsters neared the Standard Oil Building's entrance, the busy morning calm was shattered by the loud sounds of gunfire emanating from two gunmen who were firing at them from a nearby sedan. Pedestrians screamed and yelled, and Weiss joined most of them in ducking for cover. Drucci knelt behind a mailbox, pulled his own gun, and returned fire. Over thirty shots were fired in the adrenalized melee, with stray shots breaking nearby plate glass windows and hitting parked cars. Despite the bad intentions, the only casualty was an innocent bystander named James Cardan, who was grazed in the leg.

The two triggermen jumped from their car and rushed forward to get a clearer shot at Drucci's defilade position. Just then a squad of police hurried into the block. At the sight of the blue uniforms, the attackers' getaway driver evidently panicked, as he hit the gas and left his comrades behind. Weiss and one of the assailants managed to vanish into the gathering crowd. Drucci ran into the street, jumped on the running board of a stopped automobile, and jammed the barrel of his still-warm revolver against the head of motorist C.C. Bassett. "Take me away, and make it snappy," he yelled. Police yanked him away before Bassett could comply with that command.

The cops also managed to catch the second gunman, an Italian man of about thirty who was dressed in a gray summer suit and straw boater. The suspect had smartly ditched his weapon as he ran away and claimed that he had only fled the scene so he wouldn't be hit by a stray bullet. The man gave his name as Paul Valerie and his address as 3533 Walnut Street, both of which would turn out to be false. Police eventually released him from custody when Vincent Drucci claimed to have never seen the man before. For his part, Drucci denied that the gunfight was gang-related, claiming that it was merely a stick-up gone bad. The gangster was charged with carrying concealed weapons and assault with intent to kill. Mary Weiss, Hymie's mother, signed bonds totaling $5,000 for the release of her son's associate.

A Chicago Tribune rendition of the Standard Oil Building gunfight.

While the cops may have been in the dark about what the Michigan Avenue gunplay was about, Hymie Weiss and his men had no doubt who his would-be killers worked for. While the sheer number of adversaries and the steel window shutters made Capone's Hawthorne Hotel headquarters virtually impervious to an armed assault, one of the facts that had been tortured out of chauffeur Tony Cirringione was that Capone frequently ate lunch at the Hawthorne Restaurant, located just east of the hotel. In this eatery, on the ground floor and out from behind the steel shutters, Weiss knew his enemy would be vulnerable. After contacting their South Side allies, the North Side gang boss planned a spectacular attack that would not only get rid of Al Capone but strike fear into the hearts of every member of Chicago's underworld.


September 20, 1926

That Monday began fair and cool in the Chicagoland area, with the temperatures peaking in the sixties. Local newspapers were filled with stories about the horrific carnage recently wreaked on South Florida by a large Category 4 hurricane that was presently thrashing Alabama and Mississippi; the so-called Miami Hurricane remains the costliest storm in American history.

Twenty-Second Street was Cicero's main thoroughfare. One hundred feet wide with streetcar tracks running down the center, the streets fairly teemed with pedestrians and vehicles. The Hawthorne Hotel was located on the south side of the street, with the Anton Hotel one door to the west. Also on that block were a barbershop, a delicatessen, and a laundry shop. Another notable business was the Hawthorne Smoke Shop, an ostensible tobacco shop that served as a front for one of Al Capone's lucrative gambling joints.

Capone himself had just returned to town the previous week from a trip to the eastern United States. Two days earlier, he had proudly reopened his gambling joints that had been padlocked during the law enforcement crackdown in the wake of the McSwiggin killing. Today Capone had his eye on the horse races at Hawthorne Park, as the autumn racing season had just begun a week earlier. About noon, Capone left the Hawthorne Hotel and headed next door to the restaurant for a bite to eat before he departed for the racetrack.

Clyde Freeman had just arrived in town from rural Louisiana with his wife and their five-year-old son Clyde, Junior. Freeman was a racehorse owner, and like many of the people on the block today, he and his family looked forward to attending the races. Although the street was extremely crowded, Freeman was lucky enough to maneuver his car into a parking space at the curb in front of the Hawthorne Hotel. Pre-occupied with his family, the Louisianian paid little attention to the muscular, well-dressed gentleman who stepped into the restaurant. In contrast to the Freemans, an anonymous face in the mass of people did indeed notice when Capone entered the greasy spoon for lunch. This individual quickly yet stealthily made their way to the nearest pay telephone, dropped a nickel in the slot, and said that the time had come.

The Hawthorne Restaurant featured about fifteen tables and a lunch counter. Although relatively small, the café was jam-packed with racing fans today. Sometime around one o’clock, Capone was sipping coffee at his table located in the back of the dining room. The gang boss sat facing the door so he could see everyone who entered the place. As the first race did not begin until two-thirty, he was in no hurry. The loud din of conversation hung in the air as patrons ate, drank, or perused their racing forms.

At this moment, twenty-nine-year-old Paul Ricca was walking towards the door of the Hawthorne Restaurant. Born Felice De Lucia, he had illegally immigrated to America from his native Italy with at least two murders on his hands. After arriving in Chicago in 1920 and anglicizing his name to Ricca, he found work in Diamond Joe Esposito's Bella Napoli restaurant as a maître d (his underworld nickname was ‘The Waiter'). Esposito was the Nineteenth Ward political boss and a Chicago underworld figure. By the summer of 1926, Ricca had shifted to Al Capone's crew and was now known as one of his rising stars. Ricca was now on his way to the restaurant to join his boss Capone. As Paul put his hand on the door, his finely-honed survival instincts seem to have been aroused. The young gangster looked down the block and saw something straight out of a bad dream heading right for the hotel.

Then it happened. 

The vast majority of Chicagoans in September 1926 did not know what a Thompson submachine gun sounded like. They were living in an era where television did not exist, movies were still silent, and only a fraction of them owned radio sets. Some may well have heard of the weapon, but unless they were a member of the military, law enforcement, or the underworld, the staccato drumming of that gun would have been alien enough that they may have honestly mistaken it for something else. Paul Ricca was another matter completely, as he recognized the song of the Thompson at once. Paul darted into the doorway of the restaurant and shouted a warning to Al Capone, who hit the deck just as all hell broke loose.

Several slow-moving sedans filled with men armed with three or more submachine guns and an unknown number of shotguns began firing into the buildings as they reached the Anton. Passerby screamed and yelled while breaking for cover. Bullets and buckshot strafed both hotels and the five businesses in between. Parked cars were peppered with shots. Trapped and terrified beyond belief, Clyde Freeman and his family screamed in terror as at least thirty slugs raked their car hard enough to make it rock on its axle. The caravan pulled to a stop outside the restaurant, their shots vaporizing the plate glass windows. Straight lines of waist-high and chest-high bullet holes dotted the walls and gouged out chunks of plaster. Dishes, glasses, and coffee cups jumped or outright shattered as they were struck. Patrons in the restaurant hugged the floor and plugged their ears against the loud cacophony of gunfire. Broken glass, porcelain fragments, various liquids, wood paneling, and even ceiling plaster showered down on the cowering diners. Capone remained frozen on the floor.

A man dressed in a khaki shirt and brown overalls stepped out of the second-to-last sedan, a Thompson in his hands. While the others held their fire and kept him covered with pointed weapons, the submachine gunner calmly walked to the front door of the restaurant, knelt in the doorway, and opened fire. The sight of this Angel of Death-like figure seems to have finally broken Capone's inertia, as he peeled himself off the floor and ran for his life. Bullets followed Al every step way until he made it out the café's back door. With his target now out of sight, the overall-clad submachine gunner proceeded to empty the remainder of his one hundred round capacity drum magazine into the already demolished dining room. After this final eff-you salute finished a few seconds later, the gangster walked back to his waiting automobile. A klaxon horn tooted three times and the caravan began to accelerate towards the Chicago city line two blocks to the east. As they went, witnesses noted that the final car was outfitted to look like a Chicago Police detective bureau sedan.

The scene of the crime not long after it happened. The restaurant in the left center of the photo was the focal point of the attack. Photo courtesy of www.myalcaponemuseum.com

Slowly but surely, the diners of the Hawthorne Restaurant and the other bystanders in the area emerged from their hiding places. Some women still may have been screaming, but most people were wide-eyed and panting, adrenaline still whipping through their systems. They were in a mild state of shock and still trying to mentally process what had just happened. Some accounts say Al Capone was discovered in a shop next door to the restaurant, while others state that he had re-entered the restaurant after the shooters had left; contemporary accounts make no mention of Frank Rio at all. Wherever he was, Capone was soon jerked out of his reverie by the screams of a woman coming from a nearby parked car. It was Clyde Freeman's wife. Capone instantly ran outside to see what he could do to help.

The police later claimed that the gunmen had fired about one thousand rounds (this seems to have been a bit of exaggeration; a careful review of the available evidence suggests that a total in the mid-to-upper hundreds range is more accurate). A slew of parked cars (thirty-five, by one reckoning) had been hit by gunfire. To this day, it is uncertain exactly how many cars were in the attacking caravan. Witnesses told differing accounts. The first reports filed later that night varied by newspaper, some saying that there were three or five vehicles, with the most reliable witness accounts settling on the neutral "several." As time went on, journalists and authors eventually added more cars to the tally; eight, ten, twelve, a baker's dozen; most modern renderings of the attack are divided between eight and ten vehicles.

Similarly, the number of shots fired in the drive-by gradually grew in retellings; one thousand, fifteen hundred, and so on. One recent venture was that a whopping two thousand rounds were fired that day; to show how logistically unfeasible that particular claim is, the raiders would have had to (at minimum) man a total of twenty submachine guns, each fitted with a one hundred round capacity drum magazine that would empty once. That is, of course, if not one of those drums jammed or misfed during operation.

Another oft-told detail of the Hawthorne drive-by involves a Chicago Police detective sedan rolling a block in front of the caravan featuring a submachine gunner firing blanks, a noisy ruse calculated to disperse bystanders and draw a curious Capone either to the street or the front of the café for easy elimination. The problem with this statement is that the Model 1921 Thompson is a friction-delayed blowback firearm. As such, its basic operation depends on high chamber pressure generated by a propellant to push the breech block to the rear, thus enabling the weapon to chamber and fire a new .45 caliber round. If a blank cartridge is used, there is no bullet traveling through the barrel, and the combustion gases will escape through the muzzle without building up enough pressure to chamber and fire the next round. Thus, the submachine gun will not fire blanks unless a constricting device is attached to the muzzle in order to build up enough chamber pressure to facilitate the blowback action. If the gents in this detective sedan were only looking to make some noise, a far easier solution would have been to just fire standard live rounds straight up into the air. Even more importantly, none of the original witness accounts taken at the scene mention such a vehicle. It appears that the blank-firing point car is one of more than a few canards that would pop up in the wake of the attack.

All outlandish claims aside, the drive-by shooting was indeed a savage event, and it was truly miraculous that no one was killed that day. Three of those injured were the unlucky Freeman family, whose car was turned into Swiss cheese by the assailants. Clyde Freeman's knee was grazed by a bullet, as was the scalp of five-year-old Clyde, Junior. Missus Freeman was hit the worst, as a submachine gun bullet passed cleanly through her arm. Despite their injuries, all three Freemans were given a "clean bill of health" by a doctor later that evening.

Many latter-day accounts claim that a sliver of glass from the car's windshield was driven into Mrs. Freeman's eye by the gunfire, with Capone later generously paying $5,000 for the surgery to save her eyesight. Contemporary news reports filed in the immediate aftermath of the shooting make no mention of Mrs. Freeman having such an injury, and it seems unlikely that she would have been given a "clean bill of health" had she been writhing in pain from a shard of glass lodged in her eye. Additionally, the entire Freeman family had recovered enough to view and dismiss two suspects (Bugs Moran and Frank Gusenberg) that police brought before them just a few hours after the shooting. It seems unlikely that Mrs. Freeman would have been in any condition to visually identify a suspect had she sustained such a grave injury to her eye. All in all, it appears that the Mrs. Freeman eye injury/Capone-financed surgery story is yet another tall tale.

The only other casualty that day was Paul Ricca, who took a bullet in his left shoulder just after he had shouted his warning to Capone. As soon as Chicago police Chief of Detectives Bill Shoemaker laid eyes on Ricca, he identified him as the "Paul Valerie" who was busted while running away from the Standard Oil Building gunfight a month earlier. Despite being in considerable pain from his wound, Ricca was alert enough to give police the new alias of "Louis Barko" and claimed that he was "only a lone wolf gambler" or a "bookmaker," depending on which paper you read. The wounded gangster admitted to seeing the attack from start to finish but claimed he could not identify any of the perpetrators.

Paul Ricca as he appeared at the time of the shooting.
For decades it has been assumed that faithful bodyguard Frank Rio had saved Al Capone's life by yanking him to the floor of the café once the fireworks began. Judging by contemporary news accounts and modern revelations, it is uncertain that Rio was even there to begin with. Recent research by Chicago organized crime expert John Binder indicates that it was actually Paul Ricca who was responsible for keeping Capone out of harm's way that day. In 2009, Binder interviewed a confidential source close to the Ricca family who confirmed Paul's role in the Hawthorne drive-by episode. Ricca himself vividly remembered the incident in his later years. As he recounted, "One of the men got out of the car and trained a machine gun on Capone in the restaurant, but Capone fled out the back way." The grateful gang boss certainly knew how to repay the favor to Ricca, who was almost immediately moved off the street and put to work directly under Frank Nitto in the upper echelon of the Capone mob's chain of command. Capone would even act as best man at Ricca's wedding the following spring, something he reportedly never did for any of his other associates.

In warning Al Capone just as the bullets began flying, Paul Ricca not only showed a bold disregard for his own safety but also loyalty, coolness under pressure, and decisiveness. These qualities would serve Ricca well enough to see him eventually ascend to the leadership of the mammoth criminal organization Capone had built.


Aftermath

North Side gangsters Frank Foster (left) and Frank (upper right) & Pete Gusenberg were suspected of taking part in the raid. 

Even before the gun smoke had fully drifted away from the 4800 block of West Twenty-Second Street, police suspected that the North Side Gang was responsible for the Hawthorne drive-by shooting. After questioning witnesses and getting license plate numbers of the cars used in the attack, police sent out the call to arrest Hymie Weiss, Vincent Drucci, Bugs Moran, Pete and Frank Gusenberg, Frank Foster, Michael "Puggy" White, and another pair of brothers named Ben and Ernest Applequist. Also suspected of participating were South Side gangsters like John "Dingbat" O'Berta, Vincent McErlane, and George Darrow, known as the torture expert of the Soltis-McErlane mob. Gangster John Touhy was also questioned after police traced one of the caravan car's tags to him. While no one in law enforcement doubted their guilt, none of these men were prosecuted. Paul Ricca repaid the favor that Vincent Drucci had done him a month earlier and refused to identify him or any of the other suspects.

South Side gangsters John "Dingbat" Oberta (left), Vincent McErlane (upper right) and George Darrow were suspected of taking part in the raid. All three were members of the Soltis-McErlane crew.

Throughout the city, the Hawthorne raid caused shock and indignation. One newspaper headline blared, "THIS IS WAR!" While Chicago newspapers gave the shooting front-page coverage, editors felt it didn't quite rate banner headline status (such treatment indicates that the attack was indeed embellished by subsequent accounts). A modern examination of contemporary news reports shows that despite the considerable power that Al Capone wielded in September 1926, he had yet to become the iconic crime overlord he is currently remembered as. Most news stories somewhat vaguely referred to him as "Caponi" or "Al Brown," his usual alias. Most of the Chicagoland public still considered him to be a Cicero gangster, even though his influence was increasingly felt throughout the entire city.

Just about all the gambling joints that Capone had recently reopened were closed yet again by a new crime crackdown necessitated by the attack. Capone himself paid for the repairs to all the businesses and automobiles damaged in the raid. As one of his underlings said, "The Big Fellow never wants bystanders hurt." About three weeks later, Capone himself discussed the Hawthorne assault with reporters, "It has shown the authorities that I have no corner on the machine gun market. A machine gun was used to shoot up the Hawthorne Hotel a few days ago, and they can't blame that on me. Why, I'm still paying the owners of automobiles parked in front for the damage done to their cars in that raid, and I am trying to save the eye of the poor innocent woman they wounded sitting in a car in front." In trying to gain some good press for himself, Capone may have inadvertently been responsible for the start of the myth of Mrs. Freeman's injured eye.

In the nine decades since the Hawthorne drive-by shooting, it has been portrayed numerous times in film and television, ranging from the 1932 feature Scarface (where George Raft, presumably in the Paul Ricca role, manages to bag one of the passing raiders with a single shot from a revolver before running out of the café and appropriating the fallen gunman's submachine gun) to the 2016 AMC series The Making of the Mob. Each depiction is a bit different in its make-up, much like the accounts of the witnesses themselves.

This still is of a scene in the 1967 film The St. Valentine's Day Massacre that depicts the Hawthorne raid.

In summation, the Hawthorne attack is indeed one of the key events of Al Capone's rise to power, despite the routine exaggerations of the press and the handful of myths that have built up around it (the point car shooting blanks, Mrs. Freeman's eye injury, the bullet and car counts, Frank Rio’s heroism, etc.) The raid showed that Capone was in grave danger as long as both the North Siders and Soltis-McErlane crew were simultaneously gunning for him. It is often said that Hymie Weiss was the only man that Capone was ever truly afraid of, and the Hawthorne attack is Exhibit A for that statement. Despite Capone's immense personal courage, it is obvious that this unprecedented drive-by unnerved him. In an attempt to emulate the tendency of his mentor Johnny Torrio to deal with his enemies peacefully, Capone got word to Weiss that he wanted to talk peace.


Sources

Binder, John J. Al Capone’s Beer Wars: A Complete History of Organized Crime in Chicago during Prohibition. Amherst, NY: Prometheus Books, 2017.  

Burns, Walter Noble. The One-Way Ride: The Red Trail of Chicago Gangland from Prohibition to Jake Lingle. Garden City, NY: Doubleday, 1931.

Chinn, George M. The Machine Gun, Volume IV: Design Analysis of Automatic Firing Mechanisms and Related Components. Washington, D.C.: Bureau of Ordnance, Department of Navy, 1955.

Helmer William J. & Bilek, Arthur J. The St. Valentine’s Day Massacre: The Untold Story of the Gangland Bloodbath That Brought Down Al Capone. Nashville, Cumberland House, 2004.

Keefe, Rose. The Man Who Got Away: The Bugs Moran Story. Nashville, Cumberland House, 2005.

Kobler, John. Capone: The Life and World of Al Capone. New York: Putnam’s, 1971.

Pasley, Fred D. Al Capone: The Biography of a Self-Made Man. Pub. 1930. Reprint 1971; Salem, NH: Ayer, 1987.

Schoenberg, Robert J. Mr. Capone. New York: William Morrow & Company, Inc., 1992.

Anthony Cirringione Death Certificate. State of Illinois, Cook County, Department of Public Health – Division of Vital Statistics, Registration #1115, 1926.

Chicago Daily News, September 20, 1926

Chicago Herald & Examiner, September 21, 1926.

Chicago Journal, October 13, 1926.

Chicago Tribune, August 4, 11-12 and September 21-23, 1926.

The Hawthorne Hotel at Mario Gomes's myalcaponemuseum.com

Hymie Weiss at Mario Gomes's myalcaponemuseum.com

Vincent Drucci at Mario Gomes's myalcaponemuseum.com

16 July 2019

New York gangster Johnny Spanish: A Retrospective (1 of 2)



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One hundred years ago this month, New York City gangster Johnny Spanish was dramatically gunned down in front of a Second Avenue restaurant in Lower Manhattan. The shooting, witnessed by at least a hundred people, was the final act of a criminal career that wound through the mean streets of the Lower East Side and the foreboding cells of Sing Sing Prison. Although not a household name, Spanish's name is familiar to most crime buffs mainly because of Herbert Asbury's 1927 gangster classic Gangs of New York. Known primarily for his violent feud with fellow gangster Nathan "Kid Dropper" Kaplan, Johnny Spanish's life is little known outside of what Asbury sketched of him. It has been variously said that he was a Spanish Jew; that he was related to the notorious "Butcher" Weyler, the Spanish general who ruled over Cuba with an iron fist; that he shot a pregnant ex-girlfriend in the stomach, among other things. In addition to examining his violent demise, the author hopes to separate fact from fiction and provide a more accurate picture of who Johnny Spanish really was.

He was born Giovanni Mistretta in 1889, most probably in Lower Manhattan, to an Italian father and a Spanish mother. Giovanni had at least two older siblings (Antonietta and Antonio) and a younger brother (Giuseppe). Virtually nothing else is known of his childhood, about how he progressed through adolescence and found his way into the street gangs of the neighborhood. Giovanni seems to have been relatively intelligent,  able to read and write well. As an adult, it was noted that he spoke fluent Italian, Spanish, and English. Sometime during Giovanni's youth, his family anglicized their surname to Mestrett. Thus, Giovanni Mistretta became John Mestrett. While young John may have naturally bright, he showed little inclination for academics and soon found his way into the streets. Almost certainly fueled by the hair-trigger temper that would plague him all his life, John quickly began getting into street fights. Sometime in his teens, if the standard accounts are accurate, John Mestrett found his way into the lower rungs of the notorious Five Points Gang.

One of the more storied street gangs in New York City's history, the Five Points bunch got their name from the convergence of four Lower East Side streets; Anthony (present-day Worth), Cross (present-day Mosco), Orange (present-day Baxter), and Little Water (defunct). The five points of this intersection were home to a large gang consisting mostly of Irish immigrants around the mid-nineteenth century. By the turn of the century, the Five Points Gang had grown so much that satellite branch gangs had popped up in other areas of Manhattan and Brooklyn. As the demographics changed on the old Five Points turf, so did the ethnic make-up of its ranks; by 1900, the Five Pointers were now composed mostly of Italians, with quite a few Jews and Irish sprinkled into the mob. They were led by Paul Kelly (Paolo Antonio Vaccarelli), a former boxer turned refined gang boss. The brilliant Kelly was able to forge an alliance with the corrupt Tammany Hall city government. In exchange for committing numerous instances of Election Day political terrorism and voter fraud on Tammany's behalf, the powers-that-be turned a blind eye while the Five Pointers made their living stealing and operating brothels and dance halls.

The Five Points Gang's chief rival was a giant mob of mostly Jewish hoodlums led by a former dance-hall sheriff (bouncer) named Edward "Monk" Eastman. A legend in his own lifetime, Eastman was a ferocious street fighter who led his men into action against the hated Five Points mob regularly.  On one occasion in September 1903, they staged a pitched gun battle on Rivington Street that left three men dead and a score of others wounded. At one point, Eastman and Kelly agreed to face off against each other in bare-knuckled combat in an abandoned barn in neutral Bronx territory; the two gang bosses battered each other to a draw. After Monk Eastman was sentenced to prison in 1904 for a botched robbery, his gang began to splinter. As a result, Kelly's Five Pointers were then noted as the most powerful gang in the city.

It was most probably around 1905-1906 that the teenaged John Mestrett began moving within the Five Points Gang. He most probably started small, picking pockets on crowded streets and trolleys before moving up to burglary and armed robbery. Due to his Latin heritage, Mestrett soon became known as "Spanish John" amongst the Five Points crowd. Before long, it was inevitably transposed into "Johnny Spanish." His brother Giuseppe (Joseph) soon joined him on the streets; he would be appropriately nicknamed "Joey Spanish." Despite an undersized build, Johnny attacked an opponent with the ferocity of a wolverine. Sometime during his Five Points apprenticeship, Johnny sustained a bullet wound to the face that knocked out three teeth and left an ugly scar on his cheek near his mouth. By the mid-1900s, the monolithic Five Points Gang followed the Eastman Gang's led and began to fragment into independent crews. Two former Five Pointers, Biff Ellison and Razor Riley, attempted to kill Paul Kelly at the New Brighton hall in November 1905. Kelly was wounded in the gunplay, his life saved when bodyguard Bill Harrington took a fatal bullet meant for his boss. While Kelly survived his wounds, he began easing himself out of the day-to-day business of running the Five Points mob.

Virtually no precise information about Johnny Spanish's early criminal career has survived; he was basically one of the many faceless Five Points thugs who wreaked havoc amongst the slums of the Lower East Side. However, subsequent events show that Spanish was a cut above the usual East Side thug. Intelligent and industrious, he appears to have broken away from the Five Points mob sometime around the age of twenty. Despite his Italian/Spanish heritage, most of the hoods he attracted under his banner were Jewish. As a result, many accounts have labeled John Mestrett as a Spanish Jew. In fact, like Monk Eastman before him, Johnny Spanish was a Gentile who merely moved within the Jewish-American underworld. When he was subsequently sent to prison in 1911, Spanish declared his religion as "Protestant." Upon his 1919 murder, John Mestrett was given a Catholic burial in Queens' Calvary Cemetery. Despite his ability to captain a crew of young thugs, Spanish remained temperamental and something of a loner. Herbert Asbury described him this way; "Spanish was very taciturn and morose, and was inclined to brood over his troubles, real or imagined...Spanish never stirred abroad without two revolvers stuck in his belt, and when he was on important errands he carried two more stuffed into his coat pockets, besides the regulation equipment of blackjack and brass knuckles."

By the year 1909, Johnny Spanish was a twenty-year-old crook that bossed a group of mostly Jewish thieves on the Lower East Side. As his criminal career progressed, Johnny and his brother Joey began using the alias of Weiler (also spelled Wheiler in some contemporary sources). Like most criminals of the era, they appear to have modified their names to shield their families from shame. Herbert Asbury wrote that Johnny claimed to be related to Valeriano Weyler y Nicolau, the Spanish general and colonial administrator of Cuba and the Philippines whose brutal tactics in crushing the Cuban Rebellion earned him the nickname of "Butcher Weyler." No contemporary source confirms Johnny Spanish making such a claim, and while it is uncertain if it has any merit, his mother Rose was noted as using the name "Weiler" in the 1920 Census. It's possible that this may have been a variation of her maiden name. Regardless of the Weyler connection's veracity, it is easy to imagine Johnny letting the hoods of the Lower East Side think he was kin to Butcher Weyler, as such a claim would merely add to his growing mystique. Indeed, quite a few young Jewish hoodlums hitched their wagon to Johnny Spanish Train as the decade came to a close. Some of those who rolled with him were his younger brother Joey, Hyman Benjamin, and "Lefty" Kantor. Johnny's most gifted recruit would turn out to be his eventual nemesis.

Nathan Caplin was a muscular Jewish youth the same age as Johnny Spanish. Accounts are mixed as to how Caplin came upon his nickname of "Kid Dropper." The most widely told story was that Nathan worked a scam as a Lower East Side youth where he would perform the "drop swindle," which featured Nathan dropping a wallet filled with counterfeit cash near an unsuspecting mark. As the pigeon reached to pick up the wallet, Caplin would swoop in and snatch up the billfold. Nathan would then tell the target that he was in a hurry and offer to let them have the wallet of "cash" in exchange for some slight compensation. Then, the victim could take the wallet to its rightful owner and collect an even bigger reward of their own. The second origin story for the nickname was much more coarse, stemming from Caplin's ability to "drop" his opponents with just one blow of his fist or knife. Like Johnny Spanish, Caplan came from the impoverished neighborhoods of the Lower East Side, stealing from pushcarts and unsuspecting passerby. Also, like Spanish, Caplin sought to shield his family and confuse the cops by modifying his name, to Kaplan. The Dropper presented a daunting mix of brains and brawn and was much more gregarious than the mysterious Spanish. Despite their personality differences, the two hit it off and began to cut a swath through the Lower East Side.
   
Nathan "Kid Dropper" Kaplan around the age of twenty.

In 1909, the Lower East Side gang scene was in something of a state of flux. Monk Eastman's successor, Max "Kid Twist" Zweifach, had been gunned down at Coney Island with his bodyguard Samuel Pristrich aka Cyclone Louie a year earlier by a Five Points gangster named Louie "The Lump" Pioggi. After an extended period, the Eastmans had been taken over by Abe Lewis, a first cousin of  Cyclone Louie. Ex-Five Pointers like Jack Sirocco and Chick Tricker ran their sections of the neighborhood, but Johnny Spanish set his sights on carving out his own slice of the pie. After Abe Lewis was convicted of a grocery store robbery in the autumn of 1909 and sent off to Sing Sing Prison for nineteen years, Johnny Spanish seems to have moved in to attempt to exploit his absence by going into the "labor slugging" business. As labor unions began forming in the newly industrialized America in the late nineteenth and early twentieth centuries, companies started hiring thugs to act as strikebreakers and to discourage union activity. In response, the newly forming unions hired muscle of their own to protect striking workers and to recruit new members, sometimes by force. Both sides would often face off on the picket line, verbally and physically attacking their opponents, often with the connivance of local law enforcement. Into this tumultuous breach came Johnny Spanish and his crew, who was hired by the owners of the Triangle Shirtwaist Factory in the autumn of 1909 to break a strike.

The Triangle Shirtwaist Factory took up the eighth, ninth, and tenth floors of the Asch Building, located at the northwest corner of Greene Street and Washington Place in Greenwich Village. The factory employed about 500 workers, most of them immigrant women, who worked long hours sewing women's blouses (called 'shirtwaists' in the vernacular of the era) under crowded and unsafe conditions; the plant's owners, Max Blanck and Isaac Harris, regularly locked and chained the doors of their business in order to prevent worker theft and unexcused absences. By the beginning of November 1909, the Triangle's workers began protesting the inhumane working conditions and talked of unionizing. As a result, management locked out the bulk of the plant's workforce, roughly 500 workers. Each day on the picket line, the seamstresses were picketing in front of the Asch Building. Members of the Women's Trade Union League appeared on the scene to show solidarity with the workers and to attempt to organize them. Police friendly to Triangle management menaced them at every turn. One officer growled to a young union organizer named Helen Marot, "You uptown scum, keep out of this or you'll find yourselves in jail!" Indeed, a total of ninety-eight women were hauled off to jail for protesting.

Some of the labor organizers who picketed in favor of the Triangle Shirtwaist strikers.

While the police posed a hazard to the strikers, a more direct threat came in the form of Johnny Spanish and his gang, who verbally abused and occasionally physically assaulted the strikers. A picketer named Annie Pardwin filed a complaint against Morris Goldfarb, one of Spanish's goons. Pardwin charged that Goldfarb had, "rushed up to her, slammed her against a wall near the shop and struck her with his fist, at the same time exercising his vocabulary to its limit." Johnny Spanish himself was accused by the picketers of assaulting Joe Zeinfeld, one of the locked out workers. Spanish beat Zeinfeld so severely he had to be hospitalized. Several female picketers cried out to policemen as Spanish ran from the scene. It was reported that an officer caught up with Spanish, calmly spoke with him, and watched as the young gangster casually walked away from the scene unmolested. Eventually, the strike was settled and business as usual resumed at the factory, due in no small part to the labor slugging done by Johnny Spanish and his men. It wasn't until the Triangle Shirtwaist Factory caught fire sixteen months later - and 146 workers were killed - that the world at large finally recognized the inhumane employment practices of the plant's owners.

"All the horse shows in the world, it seems, they never try so hard to keep up interest in horseflesh, are unavailing - the last straw - night riders and bold bandits come galloping into town to shoot up folks and places mounted on taxicabs." So began the New York Sun's November 13, 1909 article that introduced New Yorkers at large to Johnny Spanish and his crew. Fresh from their successful labor slugging mission, the Spanish crew decided to go on a bit of a rampage. It seems the trouble started on the evening of Wednesday, November 10, when bandits held up the Jefferson Coterie Club on Henry Street. Whether or not Johnny and his bunch were victimized here, they decided on a grand gesture of retaliation the very next night. Automobiles were still the province of the upper crust in the autumn of 1909, as horse-drawn vehicles still significantly outnumbered cars on New York streets. For those that did not own them, there were garages around the city that would rent autos to trustworthy individuals for short periods. It's not sure if this is how Johnny Spanish and his crew procured three taxicab automobiles, but somehow or another, the young gangsters were mobile and looking for revenge. Their actions that night suggest their behavior may have been artificially induced by alcohol or cocaine.

Around 8:30 that Thursday evening, three taxicabs were noted as cruising along Broome Street until they came to a stop. Johnny Spanish and about a dozen of his crew exited the three vehicles and began visiting saloons as if looking for someone. At Pitt and Grand streets, they happened across Assemblyman Aaron Levy, who was speaking to a judge. Bullets began flying in his direction, sending the assemblyman and judge running for cover. The gunmen proceeded to shoot up windows and streetlamps in the immediate vicinity. After this attack, the Spanish crew retreated to the waiting taxicabs. Around midnight, they showed up at Max Schnur's basement saloon and shot the place up. Customers were thoroughly terrorized, and all the mirrors behind the bar were smashed by bullets. Mike Kulisky and Sam Klein, sarcastically described as "innocent bystanders" by the Sun, received minor wounds in the attack. Police were thoroughly roused and rounded up hoods from all over Lower Manhattan that night, including Jake Siegel aka Kid Jigger and a William Albert, soon to become notorious as Big Jack Zelig.

The November 1909 Triangle Shirtwaist Factory strike and the subsequent taxicab rampage gave Johnny Spanish and his crew a modicum of notoriety in the Lower Manhattan underworld. Brimming with confidence and audacity, Spanish began looking to expand into other rackets. Spanish let it be known that he and his men were available for freelance muscle work. In addition to the usual pickpocketing, burglaries, armed robberies, and labor slugging, Spanish began muscling into underground stuss games. Stuss, known outside the neighborhood as Jewish faro, was favored in the underworld as the house won all the money when equal cards were drawn, as opposed to just half in standard faro. Such an action greatly increased profits for those hoodlums who ran the game. Johnny Spanish would often approach stuss operators and demand a substantial percentage of their daily earnings under the penalty of death. Spanish's gangland spoils had enabled him to buy a new house for his family members at 31 Lexington Avenue in the up-and-coming Maspeth section of Queens. The quiet, suburban setting provided an excellent escape for members of the Mistretta family. Soon Johnny's older sister Antonietta (Kate) had moved into the house with her husband Paul Ciccarelli and their growing family. Their mother Rose and Johnny's brother Joey also called the Maspeth house home.

Around the time that he was spreading his wings in early 1910, Johnny Spanish fell in love. Like many other Lower Manhattan gangsters, Spanish had a roving eye when it came to women and picked them up wherever he could; the dance halls, the theaters, the Coney Island boardwalk during summer months. Johnny had fallen hard for an attractive nineteen-year-old girl named Beatrice Konstant (or Kaplan - no relation to Kid Dropper). Herbert Asbury wrote that Spanish, "...was seized with a burning desire to ornament his adored one with silks and precious stones." In falling in love with Beatrice, Johnny Spanish (without even realizing it) had set in motion a chain of events that would eventually seal his fate.

Like any worthy New York gang boss, Johnny Spanish ruthlessly enforced his will within his own crew and was sometimes called upon to meet out some intra-gang discipline. In early May 1910, two of his men got into a deadly feud; Charles Manheimer stabbed a fellow gangster known as "The Kid" (believed to be Kid Dropper) several times. As The Kid recovered from his wounds, Manheimer avoided his usual haunts. On the evening of May 25, Spanish and Kid Dropper caught up with their wayward comrade at the corner of Norfolk and Hester streets. Manheimer got a bullet in his back that shattered his spine. Rushed to the hospital, the severely wounded gangster growled, "If I don't get a wooden overcoat I'll get the man who shot me without help from you 'bulls.'" Twenty-three-year-old Charles Manheimer died of his wound on June 12.

Buffalo Enquirer

The fatal shooting of his former underling was all in a day's work for Johnny Spanish, who immediately decided to move in on one of the more profitable stuss games in Lower Manhattan. Jacob Siegel, better known in the underworld as "Jigger" or "Kid Jigger," ran the game in question on Forsyth Street. Herbert Asbury gave a dramatic version of the Kid Jigger/Johnny Spanish confrontation, complete with invented old-timey dialogue, in Gangs of New York. Contemporary accounts indicate that there was nothing cinematic about their brief and brutal encounter. Around ten o'clock on the warm evening of May 29, Spanish showed up at Kid Jigger's game with Hyman Benjamin. Spanish bluntly informed Jigger that he was now entitled to half of his stuss profits. While he may not have been the cold-blooded killer that Spanish was, Jigger was still a product of the mean streets of the Lower East Side. As such, he refused Spanish's extortion demand. The gang boss then informed him that he would have to fight it out in the street. After Spanish and Benjamin left, Kid Jigger prepared himself as well as he could by arming himself with a cheap .32 caliber revolver. Jigger then exited his game into the warm spring night and headed north to the intersection of Forsyth and Grand streets. 

According to eyewitness accounts, Johnny Spanish and Hyman Benjamin were waiting for Kid Jigger at the corner; there may have been three other men standing just beyond them. After a brief conversation with the gang boss, Jigger stepped back and reached for his pistol. The frantic stuss game operator managed to get one harmless shot off before his flight instinct overwhelmed its fight counterpart and he sprinted for cover while one of his adversaries emptied a pistol at him. One of these bullets, unfortunately, struck a thirteen-year-old girl named Rachael Rooten in the abdomen as she passed through the corner. As she went down screaming, Spanish and his compadres made their escape. Police immediately swarmed the scene and began investigating while Miss Rooten was rushed to the hospital. The cops collared a man who gave his name as Max Hess and who had seemed to have sustained a minor wound to his thumb in the fray. Kid Jigger eventually fell into police hands and claimed that Johnny Spanish and Hyman Benjamin were behind the trouble at the corner that evening, explicitly saying that it was Benjamin who had tried to kill him and accidentally shot the young girl. After much suffering, young Rachael Rooten succumbed to her wound on June 11.

With two very public murders now credited to him, Johnny Spanish was subjected to a citywide manhunt. While Hyman Benjamin was arrested and charged with Rachael Rooten's killing, Spanish fled the city to let the heat die down a bit. Leaving behind his gangland kingdom and girlfriend Beatrice Konstant, the twenty-one-year-old gangster reportedly cooled his heels in Detroit for the duration of the summer of 1910. When Spanish returned to New York in September, he received a considerable shock when he discovered that his beloved Beatrice had cuckolded him with one of his chief underlings, Nathan "Kid Dropper" Kaplan. His youthful passions and temper aroused, Johnny Spanish's hurt honor demanded immediate vengeance.

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