Indiana's Policewomen in the Dillinger Saga

Stories about cops and robbers usually feature -- you guessed it, the robber!  In the Great Depression era of the desperado, two women of  state law enforcement made their own imprint.  They each had problems with their public image.  One survived the era with her career intact.  The other was forced into early retirement.

In the days predating large-scale enrollment of women in policing, there was little upon which to base an opinion.  Female police officers generated reactions ranging from the good, the bad, to the ugly -- mostly the bad and the ugly.  Take for example these two women of Indiana.  Both served their official duties during the zenith of the Midwest Crime Wave, facing the boldest desperadoes of the time.  Both of these women stepped into positions that required bravery and a revolutionary, trail-blazing attitude.

Fingerprint expert Marie Grott of the Indiana State Police and Sheriff Lillian Holley of Lake County, stood out among the state police of the John Dillinger man-hunting brigade.   


At the height of the Midwest Crime Wave of 1933-1935, these two women police officers were at ground zero, the matrix of the hunt for Dillinger.   It was an interstate, embattled officialdom, a backstabbing place where officials turned on each other, talked behind each other's back, and sold each other out.  And those were the men -- Captain Matt Leach of Indiana, Inspector Yendes of Dayton, Chief Michael Morrissey of Indianapolis, to name but a few.

 Indiana State Police fingerprint expert Marie Grott worked out of Indianapolis under Captain Matt Leach.  The press flirted with "Miss Grott."  The papers described her as "comely" (dictionary, anyone?)


During the Depression-challenged job market, a police woman in Indiana could bring home the bacon to fry before her eight-to-four shift.  Indiana women who were candidates for jobs, and who happened to know the right politician, were hired.  They got state jobs with responsibility and titles.  This was the result of political patronage; most of the civil service employees in the 1930s Midwest were there because they were connected to people under Governor Paul V. McNutt. 1

Both Marie Grott and Lillian Holly were maligned in the sexist press in the days before "sexist" was even a thing.  Both were hammered and elevated at the same time.  The result of this character assassination was more deadly for Holley than for Grott.

Marie Grott is best known to Dillinger aficionados as having accompanied Terror Gang moll Mary Kinder out of Tucson, Arizona, where she had been arrested with the gang.   Grott was overqualified for the job of impromptu prison matron.  Brought to Tucson with Indiana State Police (ISP) Captain Matt Leach, Grott took charge of Mary Kinder as she was extradited from Tucson to Indianapolis to undergo a grand jury investigation stemming from her alleged role in the notorious multi-prisoner escape from the Indiana State Penitentiary at Michigan City. 2

Leach included Grott in his entourage for several reasons.  As an inner-circle member of the ISP team close to Matt Leach, Grott was trusted.  Taking custody of Mary Kinder was anticipated as an act that would be wrought with hysteria.  Kinder was to be separated from her lover, Dillinger associate Harry "Pete" Pierpont.  Mary Kinder and Pierpont nursed hatred for Matt Leach, whom they blamed for not letting them get married while in custody. 3

Grott was a rising star in the department, a fingerprint expert who would soon head the Bureau of Criminal Identification.  In Tucson, Grott kept a poker face for photographers.  No doubt, the officer was aware that one false move, in this case a smile, would ruin the credibility she was trying to establish in her career.  As a result of her intuitive knowledge of the shark tank she inhabited, she survived the era with a strong reputation.  Grott managed her high-profile moments carefully, and stayed out of the limelight whenever possible.

Grott was injured in 1933 near Michigan City while enroute with Leach to question incarcerated Dillinger gang member Ed Shouse.  While driving alone in a car with the married Matt Leach, Grott's status as a single women was somehow overlooked by the press.  The other subject of this blog, Sheriff Lillian Holley, was not as fortunate. 4

While Marie Grott was patronized, Lillian Holley was vilified.

Holly is remembered as the "lady sheriff" who had charge of the Crown Point facility when Dillinger blazed out with a wooden gun.   A year before the escape, Holley had been assigned the job of sheriff after her husband, Roy, died in the line of duty.  She would eventually be skewered as holding a job that was "too tough for a woman."

Holley was caught in the crossfire of the sensational "wooden gun" Crown Point, Indiana, escape.  The press coverage that destroyed her reputation was the result of ignorance on the part of reporters as to the true machinations behind the escape.  Add to this a desire to tap into Depression-era America's inability to accept females in policing.  While the pundits blamed Holley, the true culprits -- the politicians, prison employees and judicial officials who were involved in the bribery conspiracy -- walked away from the grand jury investigation like a  walk in the park.  It did not help Holley that she, as the sheriff, was featured next to prosecutor Robert Estill as he posed with his arm around Dillinger. She smiled and appeared to be having a good time.  It was a moment that would prove to be her undoing. 5  Shortly after the escape, the press editorialized that Dillinger flew the coop because a women was in charge. 

Lillian Holley's nephew, Carroll Holley, floated around like Estill's ghost during the period that his aunt was pilloried.   Young Holley is photographed numerous times with Estill (in photo above, behind Estill to the left).  Young Holley as the deputy sheriff, took over for his aunt shortly after the escape.  Somehow, young Holley escaped the tag of holding a job that was too tough for the nephew of the lady sheriff.   It seems in hindsight that Lillian Holley took a fall in order to allow the job to remain in her family, that young Holley would be a placeholder to allow the minions of Robert Estill to maintain control in Crown Point/Lake County.

Lillian Holley got no support from news reporters who could have added a positive voice.  Dillinger-scoop staff writers for the Indianapolis Times, in particular Basil Gallagher and William "Tubby" Toms, did not step up and use the power of their pens to vindicate Holley.  While Toms took his material from ISP Captain Matt Leach, Gallagher often wrote independent, expository features.  It was Gallagher who first labeled Dillinger gang moll Mary Kinder as the "Queen of the Gun Molls."  Had he done research into the background and experience of Lillian Holley, Gallahger would have learned some impressive facts.

Holly had been in charge of  James "Fur" Sammons for a time prior to the Dillinger debacle.  Lake County Prosecutor Robert Estill was accused by East Chicago, Indiana reporters as needing to get the powerful Sammons out of the vice and gambling districts of Gary, where he posed a threat to the existing mob structure.  Estill rushed the Chicago gangster's commitment to prison. 6

Sammons was an expert machine gunner with a rap sheet that included rape of a young girl, murder during a robbery and sentencing to life imprisonment which was commuted to a parole in 1923. 7

The fall of 1933 conviction of Sammons had been a victory for both Holley and Estill.  In the frantic efforts to protect her good name after Dillinger's escape, Holley reminded the public that she had presided over custody of Sammons, who was a far greater threat to society than Dillinger. 8

"Mrs. Lillian Holley" retired from Lake County politics shortly after the escape, and her nephew, Carroll Holley took her place.

"Miss Marie Grott" settled by 1935 into to an administrative post within the Indianapolis State Police.  That year, she became the first woman to head the Indiana Criminal Investigation Bureau. The surrounding publicity celebrated her appointment by referring to her as a "good-looking blonde." 9





"Because of her excellent work in the Dillinger and other important criminal cases, Miss Marie Grott, comely fingerprint expert, has been promoted to head the criminal identification bureau pf the Indiana State Police.  Miss Grott has herself taken 139,000 fingerprints, and is adding to her files at the rate of 1,500 per month through exchanges with other states and the Department of Justice." 

Notes:

1.  Ellen Poulsen and Lori Hyde, Chasing Dillinger:  Indiana's Matt Leach Collides with the FBI, McFarland Publications, Exposit Imprint, to be released in 2018.

2.  Basil Gallagher, "City's Queen of the Gun Moll Call Master Strategist of Terrorists," Indianapolis Times, February 1934; "Holmes Out as Kinder Counsel," Indianapolis Times, February 3, 1934.

3.  Poulsen and Hyde, Chasing Dillinger.

4.  "Marie Grott Seriously Hurt in Auto Crackup; Leach Also is Injured," The Indianapolis News, February 3, 1934.

5.  "Indiana Desperado No. 1 Now Lodged in Jail of Mrs. Sheriff Holley," Indianapolis News, Jannuray 31, 193; "Woman Sheriff Unafraid as Killer Joins her Family," misc. news article.

6.  Poulsen and Hyde, Chasing Dillinger.

7.  John J. Binder, Al Capone's Beer Wars:  A Complete History of Organized Crime in Chicago During Prohibition, Prometheus Books, 2017, 96, 97.

8.  Ellen Poulsen, Don't Call Us Molls:  Women of the John Dillinger Gang, Clinton Cook Publishing Corp., 2002, 140.

9.  The Indianapolis News, September 14, 1935; "G-Woman in the U.S. Now",:Daily Mirror, September 14, 1935.

Ellen Poulsen is the author of Don't Call Us Molls:  Women of the John Dillinger Gang; The Case Against Lucky Luciano:  New York's Most Sensational Vice Trial; and co-author of the forthcoming Chasing Dillinger:  Indiana's Matt Leach Collides with the FBI.  She lectures on the 1930s gangster era and has appeared on numerous TV documentaries, including AMC's The Making of the Mob.  She has started work on a book examining the 1934 New York State conviction and execution of accused husband "murderess" Anna Antonio.

www.dillingerswomen.com
www.lucianotrial1936.com

Survived enemies, killed by friend

NY Evening World

In the early morning of December 26, 1920, gangland legend "Monk" Eastman was shot to death near Union Square in Manhattan. It was an abrupt end to a day of holiday merry-making as well as to a decades-long criminal career.

"Monk" Eastman had spent Christmas evening celebrating with some friends at the Court Cafe at Driggs Avenue and Broadway at the Brooklyn end of the Williamsburg Bridge. Though Prohibition was in effect, bootleg booze was readily available, and the forty-seven-year-old gangster and his associates drank large quantities of the stuff.

Around midnight, the Court Cafe quieted down, and the Eastman party decided to move on into Manhattan to continue the jolly time. The group piled into a car, and Monk directed the driver, twenty-six-year-old William J. Simermeyer, to the Blue Bird Cabaret, 62 East Fourteenth Street. Eastman was a frequent visitor at the Blue Bird and was friendly with its management and staff.

After several hours of singing and heavy drinking, Eastman and friends left the Blue Bird at about four o'clock in the morning and walked a short distance east on Fourteenth Street to the corner of Fourth Avenue. Several gunshots were fired. The group quickly disbanded, leaving a collapsed Eastman dying on the curb.

Sidney Levine, master of the Brooklyn Rapid Transit subway station at Fourteenth Street, heard the gunshots and rushed upstairs to the street. He saw a body by the roadside and found a still-hot .32-caliber revolver on the station stairs.

NY Tribune

Patrons and employees from cafes in the neighborhood and taxidrivers who were parked nearby all rushed to the shooting victim. None apparently recognized him. When the sound of a heartbeat was noted, driver Peter Bailey  loaded the victim into his taxi and sped off to St. Vincent's Hospital. Eastman did not survive the trip.

Still unrecognized, his "gorilla-like" remains were moved to the morgue of the Mercer Street Police Station. Lieutenant William Funston, serving as acting captain in command of the district's detectives, took personal charge of the investigation. Detectives John Bottie and Joseph Gilinson were assigned to the case.

It was about six o'clock when the two veteran detectives had a look at the victim and instantly identified him as former Lower East Side crime czar Monk Eastman. Their identification was confirmed through police fingerprint records.

Evidence indicated that Eastman had extended his arms and hands in a vain effort to shield himself from the gunshots that took his life. There were wounds to both his forearms and to his left hand. Shots were fired at close range, as powder burns were evident on his overcoat. One slug entered at the left center of Eastman's chest. Chief Medical Examiner Charles Norris confirmed on December 27 that it was the cause of death, having pierced Monk's heart. Norris also noted that Eastman was very drunk at the moment his life ended.

No weapons were found on Eastman. Investigators did find $144, a heavy watch and chain and two pairs of gold eyeglasses, indicating that Monk's killer did not intend to rob him.

NY Evening World

Press speculation

Assistant District Attorney John R. Hennis, chief of the D.A.'s homicide bureau, became the public spokesman for the investigation. It was a challenging role, as there seemed no limit to speculation by the New York press. In just the first two days following Eastman's murder, newspapers had suggested that it was the result of a disagreement with a bootlegging or narcotics trafficking partner, that it was related to a love affair, that it was an act of vengeance by an old rival and that it was an underworld penalty for cooperating with authorities.

There was some support for each of those possibilities. Investigators in Brooklyn were certain that Eastman was engaged in bootlegging and narcotics distribution, though he had sworn off such activities following his heroic return from service in the Great War. For a time, he made an effort to stay away from gangs and rackets. He worked in an automobile accessories store and tried managing his own pet shop (he had great affection for birds and other pets and had run a pet store many years earlier). But the old life drew him back in. In recent months, police had been following him into Manhattan in the hope of identifying a narcotics supplier.

The romantic angle related to the discovery of a Christmas card signed "Lottie" that was found in Eastman's pockets. Some Eastman friends reported that he had been married years earlier. His wife had not been seen for some time, and one report explained that she died. Authorities doubted that Monk would have jeopardized his life for love, as he seemed never to place a great deal of value in the company of a woman.

NY Herald

As far as enemies and rivals were concerned, Eastman had made plenty since his days as street gang warrior, strike-breaker and Tammany Hall-hired political "slugger," but he outlived many of them. "Eat-'em-up Jack" McManus had his skull crushed back in 1905. Bullets took out Max "Kid Twist" Zwerbach in 1908, "Big Jack" Zelig in 1912, Jack Pioggi in 1914 and "Johnny Spanish" Weyler in 1919. A number of the old brawlers were still around but were giving way to a new generation of Prohibition Era gangsters.

The notion that a lifelong underworld figure like Monk Eastman might be cooperating with police seemed outrageous. However, on the day after Eastman's murder, authorities revealed that Eastman had been holding meetings with narcotics investigators. Acting Captain Daniel Carey, commander of detectives in Williamsburg, Brooklyn, went to Eastman's room, 801 Driggs Avenue, in the middle of December and again just before Christmas to discuss an investigation of a drug ring. Dr. Carleton Simon, deputy police commissioner in charge of the narcotics squad, and squad Detective Barney Boylan had also met with Eastman during the month of December. When questioned about the meetings, the police did not deny that Eastman helped to expose an opium ring.

Killed by a friend

Speaking with reporters on December 28, Hennis refused to address the press assumptions. He revealed a belief that Eastman was killed not by an old enemy but by a longtime friend. He refused to identify the suspect, who was not yet in custody.

Hennis explained that, after Eastman and a half dozen partiers left the Blue Bird, they met an old acquaintance. Eastman spoke to the man briefly before the man fired the shots that took Eastman's life. After that, the remaining partiers all scattered.

"We cannot tell whether Monk was double-crossed [by the friends he was with]," Hennis explained, "but we do know that the man who shot him was known to all the rest. He is a well known character, although not so famous as Monk."

A later announcement described the suspect as "not a gangster" but a man who was on intimate terms with criminals in the Union Square area.

On December 30, news reports indicated that the identity of Eastman's killer was learned through the questioning of driver William J. Simermeyer and Eastman friend Sylvester Hamilton, both of Brooklyn. The men were each held in $10,000 bail as material witnesses.

Wikimedia

Burial with military honors

Monk Eastman was buried with military honors on December 30, 1920. The funeral was arranged and financed by friends who had served with Eastman in the World War I American Expeditionary Force and could not bear to see him interred in a potter's field.

Infamous for his brutality on the streets of New York City, Eastman earned the respect of his fellow servicemen during the war. He volunteered for military service in October 1917, after emerging from a term in Sing Sing Prison. He enlisted in the 47th Regiment, New York National Guard, under the name of William Delaney. A short time later, part of the 47th, including Eastman/Delaney, was joined with the 106th United States Infantry and sent overseas to fight in France.

Eastman and the 106th participated in the advance along Vierstraat Ridge in Belgium in the late summer of 1918. During that battle, Eastman rescued a fallen comrade, braving enemy fire and suffering two bullet wounds. Following that act of heroism, he was sent to the hospital to recover.

Just three days later, he reportedly left the hospital, without orders and without his uniform, to rejoin his old unit at the front. Wearing hospital pajamas, it is said that Eastman single-handedly slithered through mud to a German machine gun nest and succeeded in taking the position from the enemy.

Eastman's courageous service so rehabilitated his image that Colonel Franklin W. Ward, commander of the 106th Infantry, and First Lieutenant Joseph A. Kerrigan went to New York State Governor Alfred E. Smith to plead that the former gangster's state citizenship, lost due to his felony convictions, be fully reinstated. Governor Smith agreed to the request on May 8, 1919.

On the day of Eastman's funeral, thousands came out to Mrs. Samuel Yannaco's small undertaking establishment, 348 Metropolitan Avenue, to pay their respects. Eastman's body was was dressed in his military uniform, adorned with the American Legion wounded men's button. On his left shoulder was an insignia for his military unit. His sleeves showed three service stripes and two wound stripes.

A silver plate on the coffin was inscribed, "Edward Eastman. Our lost pal. Gone but not forgotten."

At a funeral service, Rev. James H. Lockwood expressed regret at never having gotten to know Eastman: "It is not my province to judge this man's life. His Creator will pass judgment; He possesses all the particulars and is competent to judge any soul. It may startle you to hear me say I wish I had known this man in life. We may have been reciprocally helpful. It has been said there is so much bad in the best of us, so much good in the worst of us, that it does not become any of us to think harshly of the rest of us. That is one way of saying 'let him that is without sin cast the first stone.'"

The American Legion provided a military escort for the coffin to its gravesite in Cypress Hills Cemetery. Taps was played, and a final military salute was fired.

NY Evening World

Drunken quarrel with a Prohibition agent

The press learned the identity of the murder suspect and published it on the final day of 1920.

Jeremiah Bohan, a Brooklyn businessman and longtime pal of Eastman, was believed to have been part of the group of holiday revelers who accompanied Eastman from the Court Cafe to the Blue Bird Cabaret on Christmas night. Police had not found Bohan at his home or his work or any of his usual haunts since Monk was shot to death.

An interesting wrinkle in the story was provided by Bohan's appointment several months earlier as a local inspector working under State Prohibition Director Charles R. O'Connor. With Bohan's job responsibilities - ensuring compliance with the national law against the production, transportation and sale of alcohol - came a license to carry a firearm.

Authorities revealed that Bohan had a police record. He had been arrested several years earlier in connection with the killing of "Joe the Bear" Faulkner in Williamsburg, Brooklyn. He was exonerated by a coroner's jury.

Bohan had worked as a stevedore and as a retail liquor merchant before being assigned to Prohibition enforcement duties. (The assignment was the result of a recommendation by a Brooklyn political leader unnamed in the newspaper reports.)

On January 3, 1921, Bohan surrendered to Acting Captain Daniel Carey in Williamsburg and confessed to shooting Monk Eastman. According to Bohan's statement, he shot Eastman in self-defense during a drunken quarrel.

Investigators found Bohan's description of the quarrel less than believable. He said that the two men argued about whether to leave an especially large Christmas tip for Blue Bird waiter John Bradley. Eastman wanted all in his party to contribute to the tip for Bradley, who was his personal friend. Bohan claimed that Eastman became upset when Bohan objected to contributing. According to Bohan, the idea was objectionable because Bradley wasn't even waiting on the Eastman party's table.

Bohan said he left the establishment with Eastman and the rest of the group following closely behind. At the corner of Fourth Avenue and Fourteenth Street, Eastman grabbed him by the shoulder, spun him around and snarled, "Jerry, you've become a rat since you got that Prohibition job." Bohan said he saw Eastman reach for his overcoat pocket and feared he was getting a handgun. Bohan drew his own revolver, fired several times and fled, tossing the revolver into the subway entrance as he left.

Despite their years of friendship, Bohan said he felt certain that Monk was about to kill him. "I knew what his methods were," he said, "and he had his friends with him, and I thought he was going to start something which would end in my being killed. So I drew my revolver and shot him and made my getaway."

As incredible as it was, Bohan stuck to his story. When the matter came up for trial about a year later, on December 22, 1921, he pleaded guilty to first-degree manslaughter. Judge Thomas Crain of General Sessions Court sentenced him to between three and ten years in Sing Sing Prison. He served just seventeen months in prison before he was paroled.

There's much more about Monk Eastman and other gangsters of New York's Lower East Side in the October 2023 issue of Informer (available in magazine, hardcover, paperback and electronic formats). Click here.

Sources:

• Asbury, Herbert, The Gangs of New York: An Informal History of the Underworld, Garden City NY: Garden City Publishers, 1928.
• Hanson, Neil, Monk Eastman: The Gangster Who Became A War Hero, New York: Alfred A. Knopf, 2010.
• "'Monk' Eastman rewarded," New York Times, May 9, 1919, p. 24.
• "Monk Eastman, noted gangster, slain in street," New York Herald, Dec. 26, 1920, p. 1.
• "Eastman slain in feud over bootleg," New York Evening World, Dec. 27, 1920, p. 1.
• "'Monk' Eastman, gang leader and war hero, slain by rival gunmen," New York Tribune, Dec. 27, 1920, p. 1.
• "Monk Eastman's murder is laid to squealing on ring," New York Herald, Dec. 28, 1920, p. 2.
• "Eastman's slayer sought in his gang," New York Times, Dec. 28, 1920, p. 2.
• "Expect to arrest 'Monk' Eastman's murderer to-day," New York Evening World, Dec. 28, 1920, p. 2.
• "Eastman met death as drug ring squealer," New York Tribune, Dec. 28, 1920, p. 1.
• "Eastman's slayer sought in his gang," New York Times, Dec. 28, 1920, p. 2.
• "Monk Eastman's slayer identified as one of his gang," New York Herald, Dec. 29, 1920, p. 2.
• "Military funeral for Eastman as police seek nine," New York Evening World, Dec. 29, 1920, p. 12.
• "'Monk' Eastman buried as hero beside his mother," New York Tribune, Dec. 31, 1920, p. 6.
• "Chauffeurs name Eastman's slayer," New York Herald, Dec. 31, 1920, p. 2.
• "Search in vain for 'Monk' Eastman's slayer," New York Evening World, Dec. 31, 1920, p. 2.
• "Seek dry agent as missing link in Eastman case," New York Tribune, Jan. 1, 1920, p. 3.
• "Dry agent sought to clear murder of Monk Eastman," New York Herald, Jan. 1, 1921, p. 16.
• "Prohibition agent admits killing Monk Eastman after row, police say," New York Evening World, Jan. 3, 1921, p. 1.
• "Dry agent admits he slew Eastman in drunken fight," New York Herald, Jan. 4, 1921, p. 20.
• "Monk Eastman slayer gets 3 to 10 years," New York Herald, Dec. 23, 1921, p. 3.

Gangsters move to the Big Screen II

The Public Enemy  - Starring James Cagney and Edward Burns. Released May 15, 1931

This gangster pic was released four months after Little Caesar and like the latter the story takes place in Chicago. Whereas Little Caesar dealt with the Italian underworld, the former deals with Irish hoodlums.

Like its predecessor, The Public Enemy also bases some of its characters and scenes on reality. The model for Paddy Ryan’s gang was Chicago’s North Side gang. One of the main gangsters with the mob is a big shot named Nails Nathan who is a guiding force of Tom Powers (James Cagney) and his friend Matt Doyle (Edward Burns). In the movie Nails Nathan gets thrown from a horse and is accidentally killed. Upset with the death of their friend and mentor, Powers and Doyle go to the stables and shoot the horse that Nathan was riding when killed. Sounds like pure Hollywood invention right? Nope. Actually happened. The Nails Nathan character is based on an actual Chicago gangster named Samuel “Nails” Morton, a top member of the North Side gang who was popular with his associates. Just like in the film, Morton was thrown from a horse and killed while out pleasure riding and his friends really did go to the stable and kill the horse. 

Nails Morton Chicago gangster rubbed out by a horse

The main foe of the Paddy Ryan mob is the gang headed by “Schemer” Burns. Cute nickname, anyone in Chicago with that moniker? Yup, but it was a North Sider, Schemer Drucci.

In the movie, a gang war breaks out  and there is a scene where Powers and Doyle are walking along the street and rival gangsters, who have been staking out their hideout from a machine gun nest in a second story apartment window, open fire and kill Doyle. This scene is inspired by the murder of North Side gangster Earl “Hymie” Weiss who was taken out by a machine gun nest while approaching the gang’s headquarters.

The film ends with the rival gang kidnapping a wounded Powers from the hospital and taking him for a one way ride. Gangsters wouldn't actually invade a hospital to finish a job would they? Well, turns out that idea may have been snatched from gangdom as well. Though not kidnapped, a year or so before the movie was released, a Newark, New Jersey gangster by the name of John "The Ape" Passelli was bumped off in the hospital while recuperating from a botched hit. 

Any other scenes or characters that are familiar to you?

Gangsters Move to the Big Screen

The old adage, art reflects life, was never more true than with the rise of the gangster film in the 1930s.  Thanks to years of Prohibition, crime, corruption and gangland violence were at an all-time high and this was reflected in the gangster pictures released by Warner Brothers. Though a Hollywood cliche now, guys in fedoras blasting away at each other and men being mowed down by Tommy-guns was very real for the movie goer of the time.

What modern film fans might not realize is that plenty of the characters and events in these early gangster films were inspired by real gangsters and events from the era. Let’s take a look at some of the most famous of the films. We'll start the series with:

Little Caesar  Starring Edward G. Robinson and Douglas Fairbanks Jr. - released January 25, 1931.

Spoilers!

There's not a lot that was ripped from the headlines for Little Caesar but there are a few things that seem familiar to anyone who has immersed him or herself into the gangsters of old. Perhaps it's reaching but, what the hell, it's the movies lets reach.

Little Caesar was first a book loosely based on a Chicago hoodlum named Sam Cardinella, who headed a gang of bandits and extortionists during the years just prior to Prohibition. It was written in Chicago, in the late Twenties and so shadows of Al Capone, who was at the height of his career when the book was published and the film  released, can also be seen.

Robinson plays the title character Caesar Enrico “Rico” Bandetto aka Little Caesar. Rico is a small time hood with big ambitions to move to Chicago and become that City's top gangster. To this end, he and his partner in crime, Joe Massara, played by Fairbanks Jr., move to the Windy City where Rico begins his underworld ascent.  First he takes over the small gang from Sam Vettori, next he moves up another notch by displacing Diamond Pete Montana. Along the way he kills Crime Commissioner Alvin McClure.

Like the cinematic Rico, Capone was an out-of-towner who showed up in Chicago as a low level hood and had a meteoric rise to the top. Within five years of his arrival in the Windy City, Capone was running the town’s largest criminal enterprise. Unlike Rico, Capone wasn’t a small town hold-up man, he came from Brooklyn, New York where he was already involved with the Italian underworld. 

Rico or Capone?

Another incident in the film that mirrors Capone’s career is the murder of the Crime Commissioner Alvin McClure. In the film McClure shows up at a night club and, when he learns that it is owned by gangsters, he starts to leave just as Rico and his gang show up to rob it. The commissioner ends up getting killed by Rico. In real life an Assistant District Attorney William McSwiggin was bumped off in Chicago while exiting a tavern with some hoodlum pals and it is believed that Capone was one of the machine gunners who did him in.

The stuff movies are made of.

Regarding Rico’s pal Joe Massara, it may simply be a coincidence but at the time of the film’s release the most powerful Mafia kingpin in New York  was a Capone ally named Joe “the Boss” Masseria. Unlike Massara in the film, Joe the Boss would not have a happy ending. About four months after the release of Little Caesar Masseria was gunned down in a Coney Island restaurant. 

Joe Massara- Movie gangster

Joe Masseria- Real Gangster

One of Rico's early bosses is the rich and successful Diamond Pete Montana, Rico at first admires  and then surpasses him. In 1928 wealthy Chicago gangster/politician Diamond Joe Esposito  said to have been a Capone nemesis, was bumped off.

With the popularity of Little Caesar at the box office, Warner Brothers went into high-gear and mined Chicago and New York's underworlds for box office gold. 

Have you seen Little Caesar? Did you notice any other scenes or characters that the writers "borrowed" from the underworld?