from Madam: The Biography of Polly Adler, Icon of the Jazz Age
from Doubleday, November 2, 2021
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.
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.
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.
“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
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.
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.
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.
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.” 
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.” 
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. 
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.
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.
“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.” 
“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.” 
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.
pleasant”: HNH, 102.
 “Murder trade”: NYT,
July 8, 1928, 111.
 “Of the evening”: HNH, 295.
something”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.
 “Smart money”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.
 “Inside the ring”: Dempsey, Dempsey, 136.
 “Long Count”: Heimer, The Long Count.
 “Bet a million”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.
man is Dempsey”: PA to VF, Oct. 13,
1941, VF notebook, 14, VF-HNH.
 “Still don’t”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.
 “Grand host”: PA to VF, Oct. 13, 1941, VF notebook, 14, VF-HNH.
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.
Al Capone, Chicago, Broadway mob, Debby Applegate, Polly Adler, prostitution,
Jack Dempsey, boxing, Metropole Hotel