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.”  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.”  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.” 
“I’ll not forget the fight in Chicago, that was really something,” Polly later wrote. 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.” 
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. 
"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.
“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.” 
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.” 
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.”  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.
 “Very pleasant”: HNH, 102.
 “Really something”: 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