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Authors: Gus Russo

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Hill was brought into the Outfit’s confidence by Jake Guzik’s chief lieutenant and money launderer, Joe “Joey Ep” Epstein. As the man responsible for the collection of the gang’s moneys from racetracks, handbooks, studio shakedowns, and other sundry ventures, Epstein was always casting about for nonsuspicious methods of transporting the money back to the gang, laundering it, and finally, depositing it in the Outfit’s numerous offshore and Swiss bank accounts. One of his tried-and-true methods was the enlistment of classy-looking women who would not invite suspicion from the authorities. At this time, according to a friend, Epstein was employing the services of three women from the Near North Side. Epstein decided to groom Hill for the job and furnished her with the finest upperworld wardrobe and coiffures. In time, Hill distinguished herself from her peers and became Epstein’s top courier. Hill began traveling from city to city under dozens of aliases, collecting the gang’s lucre, and often cleaning it at the tracks herself. With Epstein calling the shots, Hill took thousands of gang dollars to the tracks, where she was directed to bet on races where the winner had been predetermined. Hill then brought the “new money” back to Chicago, and from there to Switzerland.

In her insatiable quest for fame and celebrity, Hill had dalliances with countless gang bosses in every major city, including one, still known only to a handful of insiders, with Moe Dalitz, of Detroit’s Purple Gang. (This liaison would play a pivotal role in one of gangland’s most infamous rubouts, that of Bugsy Siegel.) Epstein and the Outfit soon decided to offer Hill an even more dangerous assignment: She was asked to spy on prominent bosses throughout the country, such as New York’s Joe Adonis (Doto), with whom the Outfit had entered into partnerships. When in Chicago, Hill became the Outfit’s token female member, the first (and only known) woman invited to sit at the backroom table of Accardo, Humphreys, and the rest. And for her critical role in the Outfit’s smooth running, Hill was well compensated. Not only did she receive a healthy commission for moneys delivered, but she was also tipped to numerous fixed races (known by the hoods as boat races), allowing her to bet heavily and win big. No one knows exactly how much Hill was worth at her peak, but she owned or leased posh homes in many big cities such as New York, where she encouraged the rumor that she was, according to the
New York Journal-American,
a “twenty-three-year-old Georgia oil heiress.”

In New York, Hill became grist for the society and gossip columnists, who regularly reported on her legendary parties. In 1941, the
Journal-American
called her a “much photographed Manhattan glamor girl.” The paper also gave her the distinction of being the woman with the most fur coats in the country. (The wags were unaware that Hill supplemented her income by selling “hot” furs to her society girlfriends. Hill had seen how many gamblers were pawning off their wives’ furs to her real Chicago love, gambling boss Ira Colitz. Hill convinced Colitz to convert his North Clark Street Clover Bar backroom into a walk-in cooler to store furs that Hill in turn sold to her uptown pals; Hill also occasionally trafficked in hot diamonds acquired in the same manner.) In time, Hill would cast her spell on more top hoods in every sector of the nation, making a fateful assignation with Ben Siegel, about which much more will be seen.

In addition to his Colony Club investment, George Browne diversified into the profession of benefit-concert promoter. With Chicago’s Grand Opera House as his main venue, Browne promoted a series of concerts featuring a virtual who’s who of the legitimate stage: Sophie Tucker, Amos V Andy, Helen Morgan, Fanny Brice, Gypsy Rose Lee, and the Ritz Brothers, to name a few. Of course, 100 percent of the costly $20 tickets sold “benefited” only George Browne’s personal bank account.

The Outfit elite making the trek to Hollywood found themselves warmly received by the fawning studio heads and, after some encouragement, began to buy into the studios as silent partners. With insider information from the moguls’ bookie, Johnny Rosselli, the gangsters knew more about the studio chiefs’ financial condition than even their own families. One word from Johnny about an executive with vigorish problems was all that was needed for the gang to offer their lending services. While some hoods became consultants on gangster flicks, Johnny Rosselli and New Jersey boss Abner “Longy” Zwillman became full-fledged producers, together responsible for more than half a dozen box-office hits. Not surprisingly, their crime-genre films were praised by critics for their realism.

Even the hoodlums’ kids found something to appreciate about their parents’ association with Hollywood. Children of Outfit members have described private, “closed set” tours of the Hollywood studios, conducted not by teenaged tour guides, but by the movie moguls themselves, much to the dislike of their contract players. On all their trips West, the gangsters were “comped” by IATSE, with all travel expenses charged to the union. Louis Campagna had a preference for his union-supplied seaside digs in the expensive Malibu enclave. The gang’s new friendships in Tinseltown occasionally provided more practical benefits. On at least one occasion, Joe Accardo hid out with Hollywood producer Howard J. Beck while he was being investigated in Chicago by the Civil Service Commission. Other Outfit hoods on the lam, among them Butch Blasi and Sam DeStefano, were dispatched to Hollywood, where they were given cushy union jobs and temporary new identities until the heat cooled in the Second City.

Behind the scenes, Curly, Joe, and Paul called the shots. Occasionally this meant looking out for the interests of their Commission partners back East. In one instance, using trusted aide Ralph Pierce as intermediary, Curly Humphreys directed Johnny Rosselli to keep an eye on Longy Zwillman’s girlfriend. The stunning young actress, born Harlean Car-pentier in Chicago, had become a box-office sensation under the name Jean Harlow. The platinum blond Harlow, nicknamed Baby, was also the stepdaughter of Chicago mobster Marino Bello, who earned dirty money by pimping her to many studio executives.
4
Zwillman thus was reassured to learn that Johnny Rosselli would escort Harlow in Longy’s absence.

With the exception of new homes purchased out of state and in upscale Chicago suburbs, and Nick Circella’s new investments in his nightclub enterprises, the Outfit kept a low profile on their home turf of Chicago. Thriving associates who found it difficult to keep their names out of the newspapers were harshly punished. Joe Accardo and Curly Humphreys, not wishing to repeat Big Al’s mistakes, were in total disdain of any publicity. But for all their planning, the gang’s six-year-old scheme in Hollywood was about to unravel. The endgame would bring about prison terms for some Outfit bosses, who then refined their enterprise still again, giving them a future virtually unmolested by their upperworld adversaries.

1
. Other Outfit brands at the time included Great Lakes draft beer, Badger and Cream Top bottled beer, Gold Seal liquors, and anything made by their breweries: Manhattan Brewery and the Capitol Wine and Liquor Company.

2
. According to Mooney Giancana, the Outfit also used its Hollywood partner Joe Schenck to funnel a half million dollars to Roosevelt’s 1936 reelection campaign.

3
. Family friends hold that Llewella was actually an adopted child, the progeny of an illicit affair between an Outfit boss and Clemi’s sister, Isola.

4
. When she married Paul Bern, assistant to brilliant MGM producer Irving Thalberg, Bello wasn’t pleased. Two months later Bern was shot to death. Longy Zwillman had previously made a deal with Bern to bring him into the New York mob “so long as Longy can fuck the Baby.”

7.

Waking Up
in the Dream Factory

A
lthough a number of factors played into the eventual demise of the Outfit’s Hollywood spree, one largely avoidable oversight was crucial: The Outfit neglected to teach Willie Bioff how to launder money. Long experienced in the ways of rendering truckloads of bootleg cash untraceable, the gang’s failure to pass their expertise on to Willie the pimp would come back to haunt them. As previously noted, the Outfit used many methods to launder their money, especially favoring the natural subterfuge provided by cash flow at their racetracks. But in Hollywood, Willie Bioff had no clue how to avoid walking into a bank with a $100,000 cash deposit in his pocket. Ironically, of all the illegal chicanery orchestrated by Bioff, it was his benign desire to build a home that led to the collapse of his Hollywood reign. It would also temporarily derail key bosses in Chicago.

“A chain is only as strong as its weakest link” goes the aphorism, and it was the most compelling lesson learned by the Outfit in their IASTE finagling. The weak link in the Hollywood scam, to no one’s surprise, turned out to be Willie Bioff. Like so many before him, Bioff believed that by demanding payoffs in cold cash he would effectively protect himself from a paper trail of his covert criminal transactions. In the short term he was correct, but he had not learned the lesson of the bootleggers: Spending vast amounts of cash is an invitation to official scrutiny. By the time Bioff realized his mistake, he had to scramble. Thus, when he desired to place a down payment on his Rancho Laurie purchase in 1937, Bioff was by then aware that even a rookie bank officer’s eyebrows might raise at the sight of a thousand $100 bills dropped on his desk. In what would prove to be a fatal move, Willie Bioff turned to Joe Schenck to launder his funds and bail him out of his predicament.

Since Bioff had facilitated the Schenck brothers’ money laundering on numerous occasions, he expected, and received, a quid pro quo. Instead of depositing his cash in the bank, Bioff consigned it to Joe Schenck, who in return made out a company check to Willie for the same amount, $100,000. With his money now in a nonsuspicious form, Willie marched down to the bank and deposited a Twentieth Century-Fox business check, which he could claim, if asked, was a commission payment for his film-stock agenting deal. The transfer went unnoticed for the better part of 1937. However, when one of Willie Bioff’s growing number of enraged adversaries was pushed to the brink, the exchange was brought to light, triggering a series of events that ended with the collapse of the entire enterprise.

A number of disparate forces had opposed Bioff’s handling of IATSE, but had been stymied in their attempts to oppose the powerful Bioff-Browne-Rosselli-Outfit alliance. Bioff’s enemies were too numerous and motivated, however, to give up the fight, and their diligence was soon to be rewarded. One such foe, a coalition known as the IA Progressives, engaged in pitched battle with Bioff’s IATSE muscle. Courageously led by Irv Hentschel and Jeff Kibre, the IA Progressives fought to “get the mob out of the union.” Forming their own scab union-within-a-union, Kibre and Hentschel persuaded growing numbers of workers to defy Bioff’s orders.

The same year he constructed his paean to domesticity in the valley, Bioff began making noise about muscling in on the Screen Actors Guild (SAG). After SAG meetings, guild members would emerge to find their car tires slashed. Other members were mugged and threatened, but despite the assault, the SAG contingent refused to capitulate. Instead, they conducted their own investigation of Willie Bioff. Under the leadership of its president, actor Robert Montgomery, SAG financed an inquiry that uncovered the $100,000 payment Schenck and Fox had made to Bioff. With the examinations by the IA Progressives and SAG making headlines, the California state legislature began its own review. Under oath, Bioff stated that the transaction was merely a loan, obtained so that he could purchase land. The Assembly’s investigation allowed them to append Bioff’s resume to include “former panderer from Chicago.” The IA Progressives seized the opportunity to distribute leaflets boldly illustrated with Bioff’s Chicago mug shot. Despite the setback, Bioff was not about to take the insults lying down. Using Curly Humphreys’ tried-and-true MO, Willie was able to nip the Assembly problem in the bud by paying Assembly Speaker William Jones and his investigator William Neblitt $5,000 to kill the investigation. The move would grant Bioff only a temporary reprieve: 1938 was a bad year to be on the wrong side of the law in California, as the political climate was undergoing one of its periodic reform movements. In Los Angeles, the public was calling for gangster-corrupted mayor Frank Shaw’s recall, eventually succeeding in September 1938. Nitti and the Outfit sensed the obvious and sent word to Bioff that he should step down from his IATSE post, at least publicly. Bioff complied with the order, but continued to draw a salary and shadow his boss, George Browne.

Whereas Nitti and the gang began to express concern, George Browne exuded confidence. At the 1938 IATSE convention, Browne came to his friend Willie’s defense. Flis oration to his delegates also included jingoistic verbiage that would conveniently be adopted by firebrand pols for the next four decades: He labeled the Progressives “Communists” and “parlor pinks.” With Browne’s Red-baiting diatribe ringing the rafters of the auditorium below him, Willie the pimp took two of his goons to Irv Hentschel’s hotel room, where they beat the daylights out of him. It was Willie’s last stand; the battle for the union had just begun.

Bartenders’ Union Redux

The year 1938 not only provided drama on the IATSE front, but also for the continuing Outfit battle for control of Chicago’s bartenders’ unions. Having successfully placed Louis Romano on the board of the five-thousand- member Local 278 three years earlier, the gangsters embarked on an expansion that appeared to backfire, but actually helped embroider the growing legend of the Outfit’s legal sage, Curly Humphreys.

The union’s business agent, George McLane, later recalled how one day in 1938, Louis Romano, accompanied by Curly Humphreys and his partner from the bootlegging days, Fred Evans, arrived at his office. Robert Satchie, president of Local 278, had died of natural causes, prompting Curly Humphreys’ decision that Romano should be elevated to the presidency of the Chicago bartenders’ union. “As they sat down, Romano told me, ’I’m taking over,’” McLane recalled. “My desk drawer was open a few inches and they noticed my pistol. Humphreys and Romano pulled pistols and ordered me away from the desk.”

“We’re taking over,” Romano repeated. “You will receive your pay.” McLane took the demand to his board, which initially refused to grant Romano and the Outfit the top spot. When McLane reported back to the Capri, Curly Humphreys gave him the Look and coldly said, “Tell us who opposes it. We will take care of it.” McLane asked his counsel what he should do. “Turn it over to them” was the reply. If McLane hadn’t made up his mind by then, he would when he reached inside his coat pocket. “They slipped me a bullet,” McLane testified. A bullet placed in a man’s jacket was the standard Outfit warning of imminent death to its recipient. McLane went on a forced three-month vacation. When he returned, Curly and Romano had formed a “joint council,” having muscled fifteen other unions to fall under their umbrella. The Outfit’s dues-paying bartender serfs had now grown from five thousand to thirty thousand.

While the Humphreys-McLane tango continued, events were quietly occurring elsewhere that marked the end of an era. In April 1939, Johnny Torrio conceded defeat to the IRS after having been charged with evading $86,000 in taxes for the years 1933 to 1935. The feds had even gotten to the near-demented Al Capone in prison and persuaded him to testify against his mentor. However, his ramblings turned out to be incoherent and useless. Although Torrio initially pleaded not guilty, he changed his plea, it is assumed, so that the prosecutors would not pry open a door that would lead them into the heart of the all-important Commission. After serving twenty-three months in Leavenworth, Torrio was paroled on April 14,1941. He had done his time like a man of honor and had earned the right to retire as a living legend among those who knew what he had accomplished in a life dedicated to forging profitable alliances. The man whose vision had created first the truce between the James Street Gang and the Five Points Gang, then organized the original Chicago Syndicate, and finally the national Commission, was fifty-nine years old when he decided to take his millions and enjoy the good life.

The same year that Torrio was sent up on tax charges, his protege, Al Capone, was liberated. On November 7, 1939, with his health in steep decline, Capone was released to his wife’s custody. He would spend the next few years in seclusion at his Palm Island estate.

Meanwhile, McLane continued to haggle with Nitti and the gang about Romano. Now the Outfit wanted the union to nominate Romano for the national bartenders’ union presidency at the upcoming convention, the ploy used so successfully with George Browne and IATSE. McLane recalled one occasion when Curly Humphreys visited him at the union office, and the master of the velvet-glove approach was in rare form. “Why don’t you have some sense? You have been in the labor game all your life, but you don’t have a quarter.” Curly promised that the Outfit would make McLane as rich as Bioff and Browne. But McLane was unyielding. “I can’t go to sleep at night,” McLane said. “I ain’t going to push people around for you or anybody else.” Humphreys was taken aback, saying, “That’s the trouble. We call it business and you call it pushing people around.”

McLane later testified that at some of these meetings he met Bioff, Browne, and Circella. Clearly, the movie scam was to be used as a template for the gang’s national control of all forms of pleasure. Eventually a compromise was reached wherein the Outfit agreed to prop up McLane himself instead of Romano for the national leadership of the bartenders’ union. When Nitti first suggested the new strategy, McLane tried to school the mobster. “I told Nitti that, as it would be known that I was an Outfit yes-man, I would wind up in the penitentiary, or in an alley.” But Nitti would hear none of it. “They told me they had run other organizations and had taken other organizations through the same channels,” McLane said, “and all they said they wanted was two years of it and they would see that I was elected.” McLane capitulated to Nitti’s demand, and just as Browne had been forced on IATSE, McLane would be installed at the top of the national bartenders’ union.

When the convention occurred, the Outfit miscalculated somehow and McLane was defeated. By this time, George McLane had had enough. He went to Chicago’s master of chancery, Isadore Brown, telling the city official of the death threats he had received from the boys from Cicero. This led to the impanelment of a Cook Country grand jury in 1940. When the state’s attorney announced publicly on June 5,1940, the subject of the grand jury’s inquiry, the gangsters had to move fast. In the days of Capone’s Syndicate, the situation would have demanded that the gang dust off their Chicago typewriters. But Curly saw things differently: If the grand jury sent up indictments, a trial might provide him a laboratory in which to field-test some legal maneuvers he had been studying. If he had done his homework properly, the trial could be the best thing that ever happened to the Outfit. Thus, instead of using force to stop McLane from repeating his story before the grand jury, Curly told his colleagues to keep their distance. Curly’s move was meant to inform his associates that they could use brains over brawn. Furthermore, there would be no intimidation of the judge or jury. His grand strategy predicated that McLane be allowed to talk to the grand jury, and that the resultant trial go forward. And talk McLane did, with his testimony culminating in the indictments of Nitti, Humphreys, Ricca, Romano, Evans, and a slugger named Tom Panton. Ricca and Campagna promptly went on the lam, probably to Hollywood. Local 278’s council was dissolved and the union placed into receivership until untainted directors could be placed in charge. Why the Outfit would so break with tradition by allowing a trial to proceed seemingly without interference would soon be made abundantly clear. The stage was now set for Humphreys’ brilliant manipulation of the legal code.

Although other attorneys were reported as defense counsels of record when the case came before the criminal court, it was actually Curly Humphreys who masterminded the legal strategy that left even his adversaries in awe. Just before the November 29, 1940, trial, George McLane reported that his union was now healthy, persuading the court to terminate the receivership. At this point, McLane’s attorney, A. C. Lewis, should have suspected something. On the first day of the trial, McLane informed Lewis that he was fired. In his place was a former judge named Alfar Eberhardt, a close friend of Curly Humphreys’. After this introductory shock, Humphreys made his grand entrance. Curly’s biographer John Morgan described the scene: “The Welshman strolled into Criminal Court, with his lawyer Roland Libonati in tow, smiling courteously at the assembly, placing his vicuna coat on the back of his chair and gracing the judge with a smile.” Knowing what was about to transpire, Humphreys must have had a difficult time stifling his glee.

Following the requisite introductory remarks, the state prosecutor swore in his crucial star witness, George McLane. After McLane gave his name and address, the bombshell exploded, ignited by a seemingly innocent interrogatory:

Prosecutor: “What is your wife’s given name?”

McLane: “I must refuse to answer on the grounds that it might tend to incriminate me.”

Prosecutor: “Do you know the defendant Murray Humphreys?”

BOOK: The Outfit
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