Showing posts with label Debby Applegate. Show all posts
Showing posts with label Debby Applegate. Show all posts

05 December 2021

 Debby Applegate

Excerpt from Madam: The Biography of Polly Adler, Icon of the Jazz Age (Doubleday, 2021)  

From Chapter 6 - "Thumbs Up With The Mob"

Polly Adler wearing her first, fabulous mink coat, strolling the boardwalk in Atlantic City in 1924 with a pal. Photo from the Polly Adler Collection courtesy of Eleanor Vera.

 After three years of Prohibition, by the summer of 1923, New York City’s underworld was booming.  “It was becoming increasingly fashionable to make money any way you could – except by working for it,” remembered Polly Adler. “It wasn’t only angle-shooters and corner-cutters and big-city sharpies who were on the ‘get-rich-quick’ kick.”[1]

Nobody was raking in the chips like the bootleggers, grifters, gamblers who orbited around Arnold Rothstein, aka the Big Bankroll, the Big Jew Uptown, or the Brain.   Some were primarily bookmakers and game runners, others had been thieves, drug dealers and strong-arms for hire before he took them under his wing.  But in the last three years, Rothstein’s proteges had become New York’s “hoodlum aristocracy.”[2]   

Polly was always cryptic about how she met Arnold Rothstein, saying only that he was “a man whom I was one day to know well.”[3]   But that winter of 1923 her brothel became a favorite hangout of the Brain’s criminal cabinet. “My clientele consisted mostly of gangsters and hoodlums,” she remembered, “some of whom were to become the big shots of the day.”[4]

Arnold Rothstein, c. 1920-1928. New York World-Telegram and the Sun Newspaper Collection (Library of Congress).

It was as gamblers that Polly became intimate with the bullet boys.  Rothstein’s informal syndicate of law-breakers ran private high-stakes poker games and floating craps games, immortalized in the Broadway musical Guys and Dolls.  To elude cops and stick-up men the games shifted every night through empty garages, hotels, warehouses, and the back rooms of speakeasies.

The most important of these early patrons – her “benefactor,” as one of Polly’s well-informed friends put it – was the rising “King of the Bootleggers,” William V. Dwyer.[5] “Big Bill” Dwyer was a roly-poly man, with a disarming smile and expressive blue eyes behind horn-rimmed glasses. Rothstein had financed Dwyer when he began expanding his operation from robbing industrial alcohol from government warehouses into international smuggling.   Big Bill had, in one gangland lawyer’s description, “an easy way about him and a fine sense of humor.”[6]  He was a glad-hander, who loved the theater and saloon life and preferred grease to violence.  

William Vincent “Big Bill” Dwyer when he was known as “The King of the Bootleggers.” Photo in the public domain.

Dwyer had recently joined forces with another of Rothstein’s proteges, Francesco Castiglia, who went by the moniker of Frank Costello. (It never hurt to have an Irish name when conversing with cops).  They were joined that fall of 1923 by Owney Madden, recently released from Sing Sing, who enjoyed a reputation as one of the most vicious of the city’s Irish gang leaders.

Big Bill and Owney were partners with another of Rothstein’s proteges, “Smiling George McManus,” in a number of lucrative gambling schemes.   George McManus was a brawny, barrel-chested fellow, with a lantern jaw and a wide crooked grin that lit up when he was in good spirits.  His family had deep ties to the NYPD, which frequently came in handy.

Big Bill and Owney were partners with another of Rothstein’s proteges, “Smiling George McManus,” in a number of lucrative gambling schemes.   George McManus was a brawny, barrel-chested fellow, with a lantern jaw and a wide crooked grin that lit up when he was in good spirits.  His family had deep ties to the NYPD, which frequently came in handy.

Both were extroverted Irishman -- Dwyer from Hell’s Kitchen, McManus from Harlem -- who relished the limelight and the role of lavish host.  They also shared that most valued of traits in a madam’s estimation: a total disregard for the value of money.  Dwyer was famous for never allowing anyone to pick up a check, no matter high the bill, and McManus was beloved by waiters, entertainers and gold diggers up and down the Avenue for dropping $20 tips without blinking an eye.  

George McManus in 1929, when he was on trial for murdering Arnold Rothstein. Author’s collection.

That fall McManus and Dwyer, along with Owney Madden’s brother Marty, were running the hottest regular crap game in New York, with action running as high as $700,000 some nights.   There was nothing like shooting craps to stoke the appetite for a prostitute, Polly soon discovered. “Money meant nothing to these fellows,” she remembered with pleasure; “they sometimes spent five hundred or more in an evening. Whoever won the crap game paid the bill.”[7]

The games didn’t start till nearly midnight and ran till four or five in the morning.  Winners looking to celebrate their good luck had to worry about muggings and kidnappings, so providing a place that was safe, secret and always open into the wee hours quickly made her joint the preferred after-hours clubhouse of the late night dice-tossers.  

“It had not occurred to me to sell drinks until one of the bunch remarked that I was a sap to let them buy their booze from a bootlegger and cart it up to my apartment,” recalled Polly. “Why didn’t I get smart and sell them drinks at a buck a throw?  I took his advice, and, in his own words, cut myself in for a nice piece of change.”[8] 

She encouraged the johns to buy drinks for the girls, padding the bills further.  Of course, a tipsy girl was an uninhibited playmate, but a sloppy drunk was no use to anyone.  So she employed an old trick of brothels, serving the girls cold tea brewed to match the golden color of rye and whiskey.  On a good night, her bar bills dwarfed her profits on the bedrooms.

McManus and Dwyer were two of the most popular men on Broadway, and with their seal of approval her house quickly gained a reputation among underworldlings as, in her words, “a sort of combination club and speakeasy with a harem conveniently handy.”[9]   

But the gangsters came at a high price.   “They were a wild bunch all right,” she mused. Like most of the male half of Broadway, they all adored practical jokes and pranks, the more elaborate the better.  “They liked a joke all right -- when it was on someone else,” especially George McManus.[10] “The kids with him played the jokes and he would get a hell of a kick out of it at my expense.”[11]

Polly could tolerate the pranks, the chiseling and small cons. Unpaid loans and bad checks – stiffs -- were regular thorns. “I have enough stiffs to paper my garage,” she groused while going through a box of old papers years later.  She was freshly annoyed by one dated October 22, 1923.[12]  “It was given to me by one of the McManus gang telling me that he was president of the bank. I was gullible enough to believe that,” she remembered. “It probably was the bastards [sic] way to teach me not to believe everything told to me.”[13]  

But it was the ever-looming threat of violence that really wore on her nerves. The brass knuckle boys were notoriously unpredictable, especially when they were on a losing streak or a drunken, coked-up spree.  To prevent friendly arguments from turning fatal, she requested the boys check their guns at the door, along with their felt fedoras and bulky overcoats.  “I usually hid them in the stove,” she remembered, “figuring it wasn’t likely anyone would get a yen to bake a cake.”[14]

While that cut down on random gunplay, it didn't do much to improve their manners. George McManus, in particular, was a dangerous wildcard. “McManus was always quiet, and a gentleman when sober,” said Polly.[15]  But when liquored up, his mood could suddenly turn mean, and his jokes became cruel and dangerous.

Nonetheless, it was a price she was willing to pay.  The gamblers and bootleggers were spending like mad and her reputation was spreading fast.  She bought herself some swell clothes and showy jewelry.  “I had a big important project those days,” said Polly. “I was saving up to buy a mink coat.”[16] On Broadway, a full-length mink was the sin qua non of the fashionable flapper, just as monogrammed silk-shirts and spotless white spats marked the new status of the bootlegger.  “I talked about it so much that when a guy was trying to make a point at craps, he’d holler, ‘Come on, little Joe! This is for Polly’s mink coat,’” Polly recalled. “They told me it brought them luck.”[17] 

Business was so brisk that it wasn’t long before she had the cash in hand.   The night she brought the coat home the fellows passed it around, while Polly chuckled gamely, playing the good sport and watching nervously in fear they would spill cigar ashes or drinks on the precious mink before she could safely stow it away. 

Later that evening, as she’d returned from the kitchen, one of the gang called out, “Put your coat on, Polly.  We’d like to see it again.”

But when she opened the closet, it had disappeared.  Polly began to panic. The fellows made a show of helping her search, clowning around as they bustled about the apartment. Suddenly, one of them cried out, “You little dope, why did you put it out on the fire escape?” The boys roared with laughter. 

“I laughed loudest and longest of all – with relief,” remembered Polly.[18] 

But not every joke was so funny.   Between answering the phones, keeping an eye on the bedrooms, and serving drinks – “whiskey for the guys, tea in highball glasses for the girls”  -- it was inevitable that there would be screw-ups.  One night, McManus picked up a glass, took a deep gulp, and began gagging and sputtering.  “I knew what had happened even before he swiveled around and hurled the glass again the wall, splattering tea far and wide,” remembered Polly. “Of course he knew he had got the drink meant for his girl of the evening, and at the rate he was paying, each drink cost more than several pounds of tea.” 

Everyone in the room froze, awaiting his response.

“Okay, Polly,” McManus said evenly, “so you got to make a living…Well, fix me another drink.”

But McManus “couldn’t stand being played for a sucker,” Polly remembered. “He had to get even.” [19]  The next evening he doctored a tray of drinks with Mickey Finns, a mild poison or emetic, usually a horse laxative mixed with crushed ice that induced vomiting or diarrhea.  Several of the johns spent the rest of the night vomiting in the alley, and the girls were so sick they couldn't work for three days. It could have been worse though; he could’ve used choral hydrate, better known as knock-out drops, employed in clip joints to rob customers.            

It was a devil’s bargain, courting them as customers.  But as she put it, “there was nothing I could do about it.  I had chosen running a house as my profession and whatever the customers did, I had to take it and keep smiling.”[20]




1. Polly Adler, A House is Not a Home (Rinehart, 1953), 144.

2. Art Cohn, The Joker is Wild: The Story of Joe E. Lewis (Bantam Books, 1957), 113. 

3. Adler, House, 32.

4. Adler, House, 55.

5. “Special Adler Supplement,” 4, Virginia Faulkner’s Notes for A House is Not a Home;  New York Times, February 2, 1934, 9.

6. Leonard Katz, Uncle Frank: The Biography of Frank Costello (Drake, 1973), 63.  

7. Adler, House, 56.

8. Adler, House, 56.

9. Adler, House, 96.

10. Adler, House, 56.

11. Polly Adler to Virginia Faulkner, Dec. 10, 1951, Faulkner Notebook, 13, Faulkner’s Notes for A House is Not a Home.

12. Adler to Faulkner, Oct. 13, 1951, Faulkner Notebook, 17, Faulkner’s Notes for A House is Not a Home.

13. Adler to Faulkner, Oct. 13, 1951, Faulkner Notebook, 13, Faulkner’s Notes for A House is Not a Home.

14. Adler, House, 56.

15. Adler to Faulkner, Dec. 10, 1951, Faulkner Notebook, 13, Virginia Faulkner’s Notes for A House is Not a Home.

16. Adler, House, 57.

17. Adler, House, 57.

18. Adler, House, 58.

19. Adler, House, 56.

20. Adler, House, 58.


DEBBY APPLEGATE is a historian based in New Haven, CT. Her first book, The Most Famous Man in America: The Biography of Henry Ward Beecher, won the 2007 Pulitzer Prize for biography and was a finalist for the Los Angeles Book Prize and the National Book Critics Circle Award for biography. Her second book Madam: The Biography of Polly Adler, Icon of the Jazz Age was published by Doubleday in November, 2021.

27 September 2021

Polly Adler as Al Capone's guest at the "Battle of the Long Count", September 22, 1927


Debby Applegate

Excerpt from Madam: The Biography of Polly Adler, Icon of the Jazz Age

Forthcoming from Doubleday, November 2, 2021


 Polly Adler as the grand madam in Chicago for the Dempsey-Tunney heavyweight championship, September 22, 1927.  Photo from the Polly Adler Collection courtesy of Eleanor Vera. 

 By the fall of 1927, Polly Adler was not merely Manhattan’s most notorious madam. She had earned a national reputation as the underworld’s preferred hostess and party-planner. The gambler Arnold Rothstein and his proteges had been her first major patrons in the flesh trade, and they introduced her to the rising crème of the criminal classes. The gaudy mob-backed nightclubs had their charms, but for more delicate negotiations – and less inhibited parties – the Broadway mob needed someplace out of public view.  A deluxe bordello was more private and more indulgent than a public watering hole, so when visiting dignitaries came to New York, Polly’s parlor became a favorite spot to entertain in style.

Her stellar reputation won her a warm welcome anywhere bootleggers, grifters and gamblers thrived, from Hot Springs to Miami, from Detroit to Los Angeles.  In September of 1927 Polly made a whirlwind trip to Chicago, to attend what was considered by many to be the last great prize fight of the decade.  Jack Dempsey, fresh from his comeback victory over Jack Sharkey in July, was challenging the Shakespeare-quoting Gene Tunney to regain the heavyweight championship in Soldiers Field in Chicago on September 22, 1927.

Alphonse “Scarface” Capone had come up in the world since his early days as bouncer in Frankie Yale’s Coney Island saloon.  Over the last few years, he’d parlayed his interest in a handful of Chicago brothels into a multimillion-dollar criminal operation.  In 1926, he catapulted to national notoriety as he battled rival Irish gangs for control of the city’s rackets, terrorizing his foes with a gruesome new weapon, the Thompson submachine gun.  Capone’s “Outfit” was now a crucial hub in the movement of liquor among Canada, the Eastern rum runners, and the distilleries and breweries of the Midwest. 

New York’s racketeers and their friends in the press congratulated themselves on their discretion compared to their western colleagues, but Capone’s ambitions worried them. Big Al reveled in the limelight, and between the bloody street battles and his personal appearances in the press, he was drawing unwelcome attention to the bootlegging business. 

Like a lot of women of the night, Polly rather enjoyed “Bighearted Al,” as he liked to be called; “I make a habit of judging people only in their relationship to me and such times as I happened to run into Al he was always very pleasant.” [1]  Frank Costello had introduced Polly to Capone early in the 20s, and she often entertained the Chicago boys when they were in town on business. 

Increasingly, the business at hand was assassination, or as the New York Times called it, the “intercity murder trade.” [2]  As competition for the New York markets became more violent, the Broadway Mob and their syndicate partners began importing killers from out of town to seize the element of surprise. It was a sort of mutual exchange program for killers that evolved into the murder-for-hire outfit dubbed “Murder Inc.” by the tabloids.

Polly remembered distinctly the night that Lucky Luciano brought Capone’s trusted hit-man, “Machine Gun Jack” McGurn, and some of the boys to the house.  She recalled, with gratitude, Lucky’s restraining hand when McGurn and Bugsy Siegel, as a practical joke, decided to rearrange the furniture. They’d carried the sofa into the kitchen and were in the process of hauling the stove into the living room, “when they noticed Charlie Lucky looking at them – not saying anything, just looking. In two seconds flat the furniture was back in place and there was no more horseplay for the balance of the evening.” [3] 

“I’ll not forget the fight in Chicago, that was really something,” Polly later wrote.[4]  Every sports fan who could hitch a ride was heading to Soldier’s Field for the fight, and wagering was reported to be the heaviest anyone had seen in years.  “I bet a Big Five on Dempsey to win,” she remembered. “I followed the smart money.” [5] 

Capone, who counted himself Jack Dempsey’s most ardent fan, had offered to fix the rematch in the former champ’s favor. Jack graciously refused. Nonetheless, the gangland czar intended to make this the social event of the season, snapping up one hundred top-price seats and inviting every major mobster in the country to fill them.  “I remember thinking in 1927 that I was more afraid of who sat at ringside than of who was waiting for me inside the ring,” confessed Dempsey. [6]


"The Battle of the Long Count" - Jack Dempsey's final attempt to reclaim the heavyweight boxing title from Gene Tunney in Solders Field, Chicago, September 22, 1927.  Photo from the author's collection.

 The Dempsey-Tunney rematch would go down as one of the most controversial bouts in boxing history. In round seven, Dempsey let loose a cascade of punches that sent Tunney tumbling to the mat. But instead of retreating to a neutral corner while the referee counted to ten as the rules required, Dempsey just stood there, delaying the referee’s count, and giving the champion several seconds to catch his breath before popping up just as the ref reached nine.  When Tunney won, depriving the once-great Dempsey of his last chance to be champ, those crucial seconds – “the Long Count” it was dubbed – became a national scandal and the wellspring of a million barroom arguments.[7]  

 “Funny how I remembered the Dempsey Tunney fight, perhaps it’s because I got a big lump on my head attending the fight,” mused Polly. “When hot shot Dempsey put Tunney to sleep on that historical long count I screamed my head off, you would think I bet a million.” [8]

“Then when Tunney kicked the hell out of Dempsey, which made him a winner, I was still screaming, this time for Tunney.  Who in the hell cared who won as long as there was a winner.  Suddenly I felt something on my noodle, probably a rock.  The guy in back said, Hey lady, you must be Nuts – your man is Dempsey.” [9]

Well, concluded Polly, “for my money the guy was welcome to Dempsey, I knew him way back and never liked him and still don’t.” [10]

The real fun came after the fight was over, in her opinion. “Al Capone ran a party for one solid week at the Metropole hotel, all the big politicians from everywhere attended the party, Judges, Mobsters, yours truly included,” Polly recalled with pleasure. “Capone was a grand host.” [11]  Senators, congressmen, show people, journalists, society sportsmen, and gorgeous women, all downing top-shelf booze and dancing to the city’s scalding-hot jazz bands. Capone himself took up the conductor’s baton to direct a swinging version of “Rhapsody in Blue.”

To commemorate the historic occasion, Polly posed for a formal photograph, looking every inch the grande dame in her diamond sparklers and fashionable fox stole. 


[1] “Very pleasant”: HNH, 102.

[2] “Murder trade”: NYT, July 8, 1928, 111.

[3] “Of the evening”: HNH, 295.

[4] “Really something”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.

[5] “Smart money”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.

[6] “Inside the ring”: Dempsey, Dempsey, 136.

[7] “Long Count”: Heimer, The Long Count.

[8] “Bet a million”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.

[9] “Your man is Dempsey”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.

[10] “Still don’t”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.

[11] “Grand host”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.



DEBBY APPLEGATE is a historian based in New Haven, CT. Her first book, The Most Famous Man in America: The Biography of Henry Ward Beecher, won the 2007 Pulitzer Prize for biography and was a finalist for the Los Angeles Book Prize and the National Book Critics Circle Award for biography. She is a graduate of Amherst College and was a Sterling Fellow in American Studies at Yale University where she received her Ph.D.  She lives with her husband the workplace writer Bruce Tulgan in New Haven, Connecticut.

Labels: Al Capone, Chicago, Broadway mob, Debby Applegate, Polly Adler, prostitution, Jack Dempsey, boxing, Metropole Hotel