Biographies & Memoirs


Playing Politics

While the G was building its tax case against Al Capone, local officials were being embarrassed into action against the gangsters. One year before Capone’s 1931 conviction, federal officers had stumbled onto a bombshell. While searching for Frank Nitti at a known Syndicate hangout, the agents discovered a list prepared by local police chief John Ryan. The one-page memo targeted forty-one gangsters for prosecution. Informed individuals asserted that Curly Humphreys had bribed an official to obtain the secret memorandum. The list found by the officers showed X’s next to eight of the names, who were Capone’s hierarchy (including Humphreys, Accardo, Hunt, and Campagna). It was learned that after Ryan had dictated it, the list had been retyped for official distribution. When the Nitti list was compared to the four copies in possession of police officials, those key names no longer appeared. Supposedly, Curly had delivered the note to Capone, who had himself penciled in the X marks and somehow managed to get the Syndicate-edited list into official circulation.

The local police were forced to escalate their inquiries into Nitti and the others. After Nitti was released from a brief tax-evasion term in 1932, he found that the heat on him had not dissipated. With the upcoming Democratic National Convention and the 1933 World’s Fair both being hosted in Chicago, local officials desired to give at least the appearance of civility. This quest manifested itself in the person of the newly elected mayor, Anton “Ten Percent Tony” Cermak. During the mayoral campaign, Capone’s Syndicate had naively thrown its considerable weight behind Cermak, believing Tony’s racketeering background would render him sympathetic to the gang’s needs. In fact, Cermak was playing a dangerous game, planning to backstab the hoods once they had helped get him elected.

“The mob doesn’t know how I really feel about them,” Cermak told Judge John Lyle days before the election. “I think I can get some support from the mob during the campaign. I’ll take it. But after the election I’ll boot them out of town.” After his 1931 ascension to the mayoralty Cermak thus joined the long list of Chicago’s faux “reform” mayors. On his first day in office, Cermak double-crossed the gangsters. Loudly promising to “assign some tough coppers” to chase out the hoods, Cermak concealed his real intent: to eliminate the Italian gangsters, who were prone to settling their differences in full public view. But more important, Cermak wanted to anoint a set of less embarrassing lawbreakers whom he could control from within City Hall. It was a pattern he had established early in his career. The newly installed mayor vowed to show the world that the upperworld ran Chicago, not the underworld.

Anton Cermak was born in 1875 in Kladno, Bohemia. After his family’s immigration to America, Tony, as he was called, worked his way out of poverty, eventually becoming an Illinois state legislator. To facilitate his chief goal in life (becoming rich), Cermak began building political organizations. While in the statehouse, Cermak assumed leadership of the United Societies, a lobby of saloonkeepers, distillers, and brewers. A Chicago historian described the arrangement: “As leader of an organization which assumed the misleading name of United Societies, Cermak aroused and organized the underworld to enforce its demand for a wide-open town. For a quarter of a century, any politician, whatever his party, who dared to support any measure that would curb the license of those antisocial hordes, was immediately confronted by Cermak, snarling and waving the club of the underworld vote.”

Simultaneously, Ten Percent Cermak maintained sideline real estate and business insurance operations. Using insider information he acquired in the legislature, Cermak’s real estate business quietly purchased land that the state soon coveted for parkland. Meanwhile, Cermak’s insurance company obtained lucrative contracts from businessmen seeking favors in the statehouse. By the time he was elected mayor, the interest-conflicted Tony Cermak, the son of a poor Chicago policeman, was worth over $7 million. But the king of insider information had even greater ambitions: His sources had told him that Volstead was going to be repealed and the time was right to seize control of the soon-to-be-legal booze and gambling rackets.

Mayor Cermak understood that Al Capone would never relinquish control of his Syndicate’s speakeasies and gambling joints. Even though Capone himself was on a fast track to prison in 1931, Cermak concluded that the same fierce independence had been inherited by the new Outfit. Thus Cermak struck a fateful alliance with a successful independent bootlegger and gambling czar named Roger Touhy.

At the time of Cermak’s election, thirty-three-year-old Roger Touhy ran a thriving slot machine and hooch operation out of the suburb of Des Plaines, fifteen miles northwest of Chicago. By 1932, Touhy and his brothers had overrun the Chicago Teamsters organization, which preferred the evil of the Touhys over the evil of Capone. Until his alliance with Cermak and the subsequent battles with the Outfit, Touhy was most notable not only for being the last major Irish bootlegger since the fall of O’Banion, but also for his continued refusal to cave in to the Syndicate. The ingenious Touhy once averted a threatened raise in police bribery fees by purchasing a fleet of Esso gasoline delivery trucks with which to secretly make his booze deliveries.

Capone had first tried to cajole Touhy into a partnership, but to no avail. Soon, Capone began a campaign of terror, kidnapping and assaulting Touhy’s men. The Teamsters bequeathed the Touhy brothers $75,000 to wage war with the Capones. In responding to Capone’s thuggery, Touhy made a monumental miscalculation: He confronted Capone in a show of bravado, threatening Capone in his own headquarters. Showing up one night at the Four Deuces, Touhy played his hand, telling Capone, “Stay out of my business. I tell you that for every man of mine kidnapped, I’ll kill two of yours.” With that Touhy turned and left. Capone may have been briefly amused by Touhy’s act of lunacy, but in time Touhy would learn that Capone had a thin skin. He never forgot Touhy’s insolence.

One of Capone’s many efforts to ensnare Touhy came in 1930, while the Big Guy was in the Philadelphia lockup. By telephone, Capone instructed Humphreys to pay a call on Roger “the Terrible” Touhy. Previously, Curly had kidnapped Touhy’s partner, Matt Kolb, prompting a $50,000 payout by Touhy. Now, accompanied by his driver, James “Red” Fawcett, Humphreys dropped in on Touhy at his Schiller Park headquarters. In Touhy’s office, Curly made his best effort to convince Touhy of the mutual benefits of an alliance, suggesting Touhy come to Cicero to form a partnership with Nitti and the Outfit. At one point in the discussion, Touhy was called out of the room to take a phone call from a Capone soldier who owed Touhy a favor. “Don’t go to Cicero, they’re going to kill you,” the informant warned.

On his return to the office, Touhy declared that Nitti should come to him if he wanted to talk. Curly feigned bravado saying, “You know, Touhy, we can take care of you anytime we want to.” Touhy grabbed an ornamental shotgun off the wall, causing Curly to tremble visibly, much to Fawcett’s surprise. Humiliated, Curly offered Touhy his limousine if he spared his life. Touhy declined the offer, but allowed Curly and Fawcett to crawl back to Cicero. Like Capone, the chagrined Humphreys never forgot his encounter with Touhy and kept a watchful eye for the chance to avenge it. Not long after Cermak’s election, the opportunity would present itself.

Touhy’s operation stood out as one of the few that had successfully resisted assimilation into the Capone organization, while Mayor Cermak’s putsch manifested itself in a precipitous rise in the number of Capone-linked mobsters killed by cops, ambushed by Cermak’s “special squad.” It was not unnoticed by the Outfit that Touhy’s vast enterprise remained curiously untouched. It was soon learned that Touhy was a longtime friend of Cermak’s, for whom he supplied barrels of beer when Cermak hosted the Cook County Board of Commissioners’ annual picnic. One of Cermak’s most trusted insiders told the Illinois parole board in 1959 that he had witnessed the formation of a Touhy-Cermak alliance. Meeting in Cermak’s office, the mayor offered to help Touhy wage a full-scale war on the Outfit. To insure that Touhy would have sufficient manpower, Cermak offered to put his five-hundred-man police force at Touhy’s disposal. “You can have the entire police department,” Cermak said.

What had to be more infuriating for the Capone gang was the apparent defection of one of their own to Team Cermak. Teddy Newberry was a gambling-club owner and ward boss from the North Side who had sided with Capone’s Syndicate after the Beer Wars against the O’Banion crew. Such was Big Al’s gratitude that he had lavished on Newberry a diamond-encrusted belt buckle. Newberry became so trusted by the Outfit that he had assisted Curly Humphreys in a protection scam as recently as early 1932. Sometime that year, Cermak apparently made Newberry a better offer, and the triumvirate of Cermak-Touhy-Newberry began plotting a serious assault on Nitti and the Outfit. The assault had a personal impact on Curly Humphreys when his trusted labor adviser George “Red” Barker was gunned down by Touhy’s killers. When word reached the Outfit that Touhy and Newberry were Cermak’s approved gangsters, Curly and the Outfit set about plotting their revenge. All the while, events in Washington would force the gang to diversify its interests; the cash cow of booze was soon to disappear.


The violence associated with Capone’s regime was the last straw in the fast-growing movement to repeal Volstead. The Great Depression and the gangster era exposed the prohibitionists’ hollow promise that banning alcohol would lead to a prosperous nation. Too late, the nation realized that, in addition to rampant alcoholism, the ill-considered legislation had created powerful gangs. Once again taking the lead, America’s women, shepherded by Pauline Sabin’s Women’s Organization for Prohibition Repeal, pushed for repeal. It was a fitting development, given that women had been largely responsible for the birth of the prohibition movement. With pro-repeal sentiment taking off, the “dry unions” were now greatly outnumbered. Newspaper polls estimated the repealers at 80 percent of the populace.

By 1931, New York governor and presidential aspirant Franklin Roosevelt had joined the campaign against prohibition, asserting that $300 million could be raised in alcohol taxes to fight the depression that had gripped the country since the October 29, 1929, stock market crash. Furthermore, booze at least provided some comfort during the Depression. For the gangsters, Roosevelt’s potential election, and the possibility of an end to bootlegging, foreboded a massive drop-off in revenue.

On February 20,1933, Congress passed the Twenty-first Amendment, nullifying the Eighteenth. Ten months later, the needed three-fourths of states had ratified the measure. On December 5, 1933, the bootleggers were officially out of business, at least the booze business. The labor rackets were in full swing, under the guidance of Curly Humphreys, while Joe Accardo concentrated on gambling. But the profits from these activities would pale in comparison to the riches that awaited the boys in a few short years. In the meantime, the Outfit experienced firsthand what Big Al had often told them: “Nobody’s on the legit.”

The Outfit’s Political Education

The Outfit-Touhy counterplots took some time to coalesce, and so by June 1932, a stalemate was in place as the Chicago elite held its breath while welcoming the Democratic national delegation. And although both Curly and Joe advised the Outfit to keep violence to a minimum, there were nonetheless more than thirty gangland murders that year.

The 1932 Democratic nomination was tightly contested by two New York governors: Franklin Delano Roosevelt (the incumbent) and former four-time governor Al Smith. The Outfit had a front-row seat to the internecine backdoor warfare that chose the candidate. The boys would put this education in politicking to good use in many future presidential contests.

Accompanying the nation’s party hacks to Chicago were members of the Torrio-Luciano Commission. In his authorized biography, The Last Testament of Lucky Luciano, New York gang chief Charles “Lucky” Luciano recalled how he arrived in town with other mob luminaries, including Meyer Lansky, Longy Zwillman, Moe Dalitz, Phil Kastel, and Frank Costello. The group also included Kansas City machine boss Tom Pendergast, who was sponsoring the ascendancy of future president Harry S Truman. The mobsters were ensconced in six-room suites at the posh Drake Hotel overlooking Lake Michigan. Whereas the delegates were hosted by the local Democratic elite (headed by Mayor Anton Cermak), the gangsters were squired by Ricca, Accardo, Guzik, and the rest of the Outfit. “They supplied all the booze we needed for free,” Lucky remembered. Luciano said that the scene at the convention was similar to that at the Drake: “Liquor was for sale openly to any delegates at stands run by the heirs of Al Capone. In the hospitality suites run by the Outfit, liquor was free to all comers, and it was poured steadily and unstintingly all hours of the day and night. The bar was never closed and the buffet tables were constantly replenished.”

The nomination proved a dogfight, with a bitter Al Smith leading a vigorous “Stop Roosevelt” faction that succeeded in denying FDR the needed support for the first three ballot votes. Then, as they would in many future presidential contests, the upperworld turned to the underworld for assistance. The candidates’ aides and their sought-after delegates swarmed to the Chicago Stockyards and proceeded to maneuver the powerful ganglords. As Luciano recalled, “We waited until the very last second, and we had Roosevelt and Smith guys comin’ out our ears. They all knew we controlled most of the city’s delegates.”

While the mobsters procrastinated, Frank Costello held a meeting with Roosevelt’s advisers. Costello’s faction required a concession of their own: As governor, Roosevelt had recently unleashed Judge Samuel Sea-bury on a civic corruption investigation, and the New York “mob delegation” wanted the dogs called off. As Luciano recalled, “When Frank got the word that Roosevelt would live up to his promise to kill the Seabury investigation - I mean like tapering off so he could save face - it was in the bag for him.” The gangsters instructed their delegates to support Roosevelt.

Luciano was saddled with the task of breaking the news to Al Smith. According to Luciano, Smith, who had long coveted the White House, broke down in tears on hearing the news. When told the details of the deal, Smith warned, “Frank, Roosevelt’ll break his word to you. This is the biggest mistake you ever made in your entire life by trustin’ him. He’ll kill you.” Ignoring the warning, the mob threw their considerable weight behind Roosevelt, who won on the fourth ballot. In the subsequent general election, Roosevelt handily defeated the incumbent Herbert Hoover. Joe Accardo’s wheelman at the time, the young Salvatore “Mooney” Giancana, allegedly told his brother years later that the Outfit financially supported the Roosevelt effort in Chicago, support that would greatly escalate in Roosevelt’s subsequent reelections. “Shit, he got to the White House thanks to Syndicate money,” Giancana supposedly told his brother (in Chuck Giancana’s Double Cross). Luciano was a bit more restrained in his summary, adding, “I don’t say we elected Roosevelt, but we gave him a pretty good push.” Although unproven, Lucky’s and Mooney’s allegations, if true, would help make sense of Outfit-related controversies a decade later.

Regretfully for the New York mob, the trap predicted by Smith proved accurate: After his inauguration the following year, Roosevelt turned Judge Seabury loose on his investigation. In The Last Testament of Lucky Luciano, Lucky talked of the hard-learned lesson:

Roosevelt had been a prick all along, but I gotta give him credit for one thing - he was really smooth . . . I always knew that politicians was crooked; that you could buy ’em anytime you wanted and you couldn’t trust ’em around the corner. But I didn’t think it was the same with a guy who was gonna be President. I never knew that muscle could buy its way into the White House. I never knew that a guy who was gonna be President would stick a knife in your back when you wasn’t looking. I never knew his word was no better than lots of racket guys’. But I guess nobody should become President of the United States on the back of a gangster.

Despite Roosevelt’s alleged betrayal, the Outfit would continue to dabble in presidential politics. Only Luciano’s close Outfit chum, Curly Humphreys, remained the voice of reason in these dealings. Three decades later, he alone would caution against the Outfit’s coddling of bootlegger/robber baron Joe Kennedy and his son Jack. Curly had not forgotten the Roosevelt double cross.

Although the Democratic convention came and went without incident, Mayor Anton Cermak remained obsessed with ridding the city of the Italian gang element before the spring 1933 opening of the World’s Fair. Local banker Rufus Dawes, brother of former U.S. vice president Charles Dawes, was directing the Chicago-hosted Fair, slated for a May 27,1933, grand opening. Given the Great Depression setting, the Fair’s name, “A Century of Progress,” seemed a contradiction. But the title was meant to illustrate the great strides made by the Windy City since its incorporation one hundred years earlier and had been in the planning stage a year before the stock market’s 1929 Black Tuesday.

Dawes and Cermak allegedly had nightmare visions of millions of Fair patrons witnessing the sideshow to which Chicagoans had become accustomed: gangland drive-by shootings. Such a spectacle could hardly be expected to lure investment capital - the real purpose of the Fair - into the city. Of course, Cermak’s actual agenda remained the same: to establish his own criminal organization. Thus the anti-Syndicate crackdown continued.

The Cermak-Outfit war finally entered its climactic phase on December 19, 1932, five months before the Fair’s opening. As the Outfit later learned from its spies, Teddy Newberry met with Cermak “special squad” detective sergeant Harry Lang, paying him the then astronomical sum of $15,000 to dispose of Nitti once and for all. Joined by Patrolmen Harry Miller and Chris Callahan, Lang drove to Nitti’s fifth-floor office at 221 North LaSalle Street, an address provided them by Cermak. The officers encountered six men, including the typically unarmed Frank Nitti. In later testimony, Callahan described what happened next: “We took the six men from the little anteroom into a larger office. We searched them. Nitti had no gun. While I held Nitti by the wrists, Detective Sergeant Lang walked up to Nitti from behind and shot him three times.” He had been hit twice in the back and once in the neck. While falling, a shocked Nitti gasped to Lang, “What’s this for?” Callahan recalled that Lang then returned alone to the anteroom and shot himself in the hand, the better to claim that he had shot Nitti in self-defense.

With Nitti’s injuries seemingly fatal, a police physician arrived and tended to Lang’s trivial hand wound while the bleeding Nitti lay unconscious. Later, at Jefferson Park Hospital, the gangster regained consciousness long enough to tell his treating surgeon (his son-in-law), Dr. Gaetano Rango, “I didn’t shoot Lang. I didn’t have a gun.” He then slipped back into unconsciousness. While Nitti appeared to be at death’s door, Lang and Miller were lauded by the City Council, given bonus pay and meritorious service awards. But back at Jefferson Park Hospital, unbeknownst to the self-congratulatory officials, Nitti was making a miraculous recovery.

When word of Nitti’s condition reached City Hall, Cermak, Lang, Newberry, and Miller were gripped with fear. They knew the Outfit’s retribution would be swift and bloody. Cermak changed addresses, doubled his personal security, and placed guards at the homes of his daughters. According to newsman Jack Lait, the Outfit placed a bomb under Cermak’s car when it was parked in the Loop, but the device malfunctioned. On December 21, Cermak, Lang, and Miller suddenly left town for an extended stay in Florida. The official explanation for the trip was Cermak’s need to recuperate from a bout of dysentery. Many, however, believed that the timing of his illness was far too convenient to be coincidental. Before his departure, a clearly shaken Cermak told a reporter that the Outfit had threatened his life, and so he had bought a bulletproof vest. His parting charge to his troops was “Wage bitter war on the gangsters until they are driven from our city.” Two weeks later, Teddy Newberry’s body was found in a ditch in suburban Indiana. He was still wearing the diamond-studded belt buckle given him by Al Capone years earlier.

Word of Newberry’s passing terrified the trio of tourists visiting the Sunshine State. Five weeks later, on February 13, 1933, Mayor Cermak attempted to mend fences with now President-elect Roosevelt, who was visiting Florida, and whom Cermak had not supported at the previous summer’s Democratic National Convention. It has been also said that Cermak hoped to persuade Roosevelt to attend opening day of the upcoming World’s Fair. What happened next eerily presaged the assassination of President John F. Kennedy thirty years later: A lone nut fires three shots at a political leader on a Southern-state tour, with rumors spreading of organized crime involvement.

After greeting Roosevelt at a public appearance in Miami’s Bayfront Park, Cermak, who had uncharacteristically neglected to don his protective vest, was shot by a former Italian army sharpshooter named Giuseppe Zangara. When his Chicago secretary rushed to his hospital bedside, Cermak managed to say, “So you arrived all right. I thought maybe they’d shot up the office in Chicago too.” The fifty-year-old Cermak lingered for three weeks before succumbing to gangrene and pneumonia, and Zangara was summarily tried and executed.

The accepted version of the murder has it that Zangara was a complete psychopath who, despite being a sharpshooter, missed his real target, Roosevelt, a man whom he paradoxically said he admired. But in Chicago, another theory held sway: Cermak’s killing was intentional, a fallout from the Outfit-Cermak power struggle. Municipal Judge John Lyle, Chicago’s fiercest and most knowledgeable antimob jurist of the era, opined, “Zangara was a Mafia killer, sent from Sicily to do a job and sworn to silence.” The expounded theory posits that Zangara, whose occupation was betting on dogs and horse races, owed the mob huge gambling debts and was ordered to kill Cermak or be tortured to death. It was also alleged that he had been promised that his mother would be cared for should he be caught in the act. Lastly, renowned criminal attorney and criminologist August Bequai learned in his research for his book Organized Crime that Zangara gave an interview shortly before his execution in which he admitted that he had been ordered by the Outfit to kill Cermak. Although, when recently queried, Bequai could not recall the source of his contention, it was likely none other than the most famous syndicated columnist of the time, Walter Winchell. Using all his powers of persuasion to finesse his way past Zangara’s prison guard, Winchell obtained the only interview with the killer. According to what Winchell told his editors, Zangara was ordered to kill Cermak, and that had he missed, the fallback plan was to assassinate the troublemaking mayor on the opening day of the World’s Fair. Winchell’s editors declined to print the story since Winchell had no way to prove its veracity. However, sixty years later, thousands of Secret Service records obtained by investigative journalist John William Tuohy virtually proved the mob-hit allegation.

It turns out that the thirty-three-year-old Zangara had immigrated to America ten years before the Cermak murder. Settling in New Jersey, Zangara became a bootlegger, which resulted in his 1929 arrest for operating a massive thousand-gallon still. After spending seven months in Atlanta Federal Prison, he relocated to Florida, where he became addicted to gambling at both the horse and dog tracks. Zangara’s addiction was worsened because most of his bets failed to deliver. According to government records, Zangara became “juiced up” and was forced to work off his vigorish by becoming a drug mule: He couriered narcotics from a south-Florida processing plant to members of the New York Commission. However, for reasons unclear, Zangara went afoul of his controllers. Documents hint that he was possibly caught cheating them out of their profits. In any event, Zangara was earmarked for elimination. However, before the hit was enacted, Paul Ricca picked up the telephone.

The Waiter called Dave Yaras, a feared Outfit enforcer and labor liaison to Florida, who was moonlighting with Zangara’s New York dope pipeline. Ricca informed Yaras that the Cermak situation in Chicago had become unbearable, and that the Outfit had decreed that Cermak should be whacked, most suitably when out of town. And he was on his way to Florida. Did Yaras have any ideas? Yaras offered up the doomed Zangara. With Ricca’s consent, Zangara was made an offer he couldn’t refuse: either be killed horribly on the spot or kill Cermak and take his chances by pleading insanity in a state with liberal laws regarding mentally unstable criminals. Zangara chose the latter.

Unbeknownst to Zangara, he had more to fear than the Florida legal system. Sources told the Secret Service that Ricca dispatched two of his best killers, Three Fingers Jake White and Frankie Rio, to kill Zangara in the post-assassination confusion. On the morning of February 13, tipped by the gangsters, Zangara first proceeded to the Bostick Hotel, where Cermak was going to privately call on the owners, Horace and May Bostick, who were longtime friends. However, by the time Zangara arrived, Cermak had departed. The owners of the hotel nonetheless remembered seeing him on the premises stalking the Chicago mayor. “Zangara’s object in coming here,” May Bostick told the Secret Service, “was to kill Cermak.”

At 9:25 that night, Tony Cermak was seated on the park’s bandstand as Roosevelt’s car approached, and while Zangara waited in the crowd of fifteen thousand, Roosevelt’s vehicle stopped mere feet from Zangara. With Roosevelt lifted onto the trunk, Zangara had a clear shot at the president’s back - but did not take it. Instead, he waited for the president to spot Cermak: “Tony! Come on down here.” Cermak walked down and spoke with the president for about three minutes, then returned to the stage area. With Cermak at one end of the stage, and Roosevelt’s car on the other side, some thirty feet away, Zangara fired three shots in Cermak’s direction. William Sinnot, a New York policeman injured in the attack, said, “He was no more shooting at Mr. Roosevelt than I was.” Mark Wilcox, a Florida congressman who witnessed the shooting, stated emphatically, “He was shooting at Cermak. There is no doubt about that. The killer waited until Mr. Roosevelt sat down and then fired.” For his part, Roosevelt agreed with the other eyewitnesses that he was not the target. For the rest of his life he reiterated the opinion that Zangara was “a Chicago gangster” hired to take out Cermak.

Upon hearing news of the attack, the Chicago police department moved to have the Miami authorities round up eighteen Outfit associates known to be in Miami. However, Chicago state’s attorney Tom Courtney, known to be in the pocket of the Outfit, countermanded the department’s request before they could send it. Meanwhile, the imprisoned Zangara, who futilely pled insanity, took the prison’s warden, Leo Chapman, into his confidence. Chapman told the Secret Service that Zangara was anything but insane, and that he was in fact linked to “some sort of criminal syndicate.” Zangara’s last words before receiving twenty-three hundred volts in the electric chair were “Go ahead and push the button. Viva Italia! Viva Comorral” Comorra is an Italian word synonymous with Mafia.

Back in Chicago, firehouses sounded their alarms in celebration upon hearing of Cermak’s death: The late mayor had hounded the firefighters with unannounced midnight raids to catch men who might be dozing on the job. In short time, Sergeant Lang was fired from the police force and tried for assault with intent to murder Nitti. After hearing damning testimony from both of Lang’s partners, the jury returned a guilty verdict. Lang, however, had other ideas. “I will blow the lid off Chicago politics and wreck the Democratic Party if I have to serve one day in jail,” he threatened to a throng of reporters. Within hours he was granted a new trial, and when bail was posted at $15,000, so many worried politicians chipped in that the court was awash in $45,000 cash. Lang was said to have chuckled when he heard. He must have laughed harder when his new trial was postponed into oblivion and never occurred. Interestingly, after his firing from the force, Lang left the Cermak sphere and sided with another crook, Maxie Eisen, a racketeer and former associate of none other than Big Al Capone.

After the trial, Nitti took a much needed vacation at the Florida home of Capone’s cousin, Charlie Fischetti. Chicago crime experts believe that Nitti never fully recovered from his injuries, suffering lasting neurological injuries that rendered him incapable of taking charge of the Outfit. Some months later, acting as the “caretaker” chief of the Outfit, Nitti returned to Chicago and met with his board at what the locals referred to as Little City Hall, on the third floor of the Capri Restaurant on North Clark Street, directly across from official City Hall. According to a union boss who was taken to the Capri, the Outfit maintained a supersecret room on the third floor where they held daily meetings. “This dining room was so private,” the labor organizer said, “that you couldn’t get in there unless the elevator operator recognized you.” In attendance were Curly, Joe, Paul, Sam Hunt, and the Fischettis. Nitti advised his crew of decisions made at a meeting at Charlie Fischetti’s Biscayne home that summer, a convocation also attended by the Lansky brothers from New Jersey, and Jack Dragna, Rosselli’s Los Angeles partner. At the Capri, Nitti ticked off an agenda largely dictated by Chicago’s position as the country’s hotel and service industry mecca:

• Invest in beer and liquor businesses, then control restaurant and bartenders’ unions to increase the sales of their own brands.

• Expand into hotel and food operations, building on the groundwork already laid by Curly Humphreys.

• Get into the entertainment business, especially nightclubs and musicians’ unions.

• Take over the race wire and bookmaking businesses.

Nitti advised his gang, “The bartenders” union is our biggest lever. After we get national control we will have every bartender in the country pushing our brands of beer and liquor.’ But Nitti was wrong. Although the control of the bartenders’ unions would be lucrative, it would pale in comparison to other schemes soon to be devised.

While waiting to assault the Touhy half of the Cermak-Touhy alliance, Humphreys, Nitti, and the Outfit spent the spring cashing in on the “Century of Progress.” Even before the gates were opened on the first day of the Fair, the Outfit reaped huge profits. With land having to be cleared on Northerly Island, just off Lake Shore Drive, and massive construction projects necessary, the organizers were at the mercy of the trucking and construction trade unions, which in turn were controlled by the Outfit. Curly and his boys saw nothing wrong with taking a 10 percent cut “off the top” on all work performed at the Fair. After all, the upperworld had been collecting its 20 percent graft for decades. That fee was the price fixed to guarantee work permits for lucrative jobs. Private contractors automatically added the fee to their job estimates, a tribute paid “to take care of the boys downtown,” as one such businessman put it. The Outfit, led by Curly Humphreys, paid a visit to the Fair’s builders and convinced them of the wisdom of tacking on the added 10 percent for the Outfit.

Held on the Lake Michigan shoreline between Twelfth and Thirty ninth Streets, the 1933 World’s Fair ran for two years, attracting more than thirty-nine million visitors. Its main theme was the number of recent scientific breakthroughs in use of lighting (the Fair’s lights were turned on when rays from the star Arcturus were focused on photoelectric cells at disparate astronomical observatories, transformed into electricity, then transmitted to Chicago).1

Not all the fair’s exhibits were high-minded. The earthy, hedonistic pleasures were in evidence, if not advertised by civic promoters: Exotic “fan dancer” Sally Rand showed her wares at the Streets of Paris emporium; wine and women flowed at the Ann Rutledge Tavern. With so much money to be made at the Fair, the members of the Outfit were not about to look the other way after construction was completed. They were, in fact, among the chief beneficiaries of the tourist largesse. While Chicago’s newest corrupt mayor, Edward Kelly, squired dignitaries around the grounds, Al Capone’s heirs controlled many of the Fair’s critical functions, including parking, hot dog, hamburger, soda, hatcheck, towel, and soap concessions. What services they did not operate outright, they nonetheless profited from by collecting “protection” money. Curly Humphreys owned the most popular ride at the Fair and, with Fred Evans, controlled the popcorn concession. While Curly was on the lam later that year in Mexico, he hired a manager who picked up the weekly profits from each booth. Al Capone’s brother Ralph virtually cornered the market on bottled water and sodas, while Paul Ricca ran the San Carlo Italian Village, where the Outfit socialized after hours. The roulette wheels were spinning and the dice rolled under the supervision of Outfitter James Mondi. Outfit boss and Capone cousin Charlie Fischetti said at the time, “If a wheel turns on the fairgrounds, we get a cut of the grease on the axle.”

When the fairgrounds emptied at night, the adult attendees partook of the Outfit’s other amenities scattered throughout the rest of the city: brothels, casinos, massage parlors, and saloons. Prohibition came to an end during the first year of the Fair, an event that only escalated the partying at the Outfit’s clubs, which operated twenty-four hours a day. With these and other gang enterprises enjoying robust business, the transition to post-Volstead was reasonably smooth.

Curly’s Revenge

With Cermak removed from the scene and the “Century of Progress” filling the Outfit’s coffers, Curly Humphreys was free to redress the personal attack by Roger Touhy, not to mention the murder of his friend Red Barker and the shooting of Frank Nitti. Humphreys’ vengeance had the added bonus of simultaneously removing a major Outfit adversary. The plot was brilliant in concept and actually played out over several decades before reaching its denouement. At the time, an English friend of Curly’s, John “Jake the Barber” Factor, was living in Chicago, on the run from the law in Great Britain. Factor, brother of future cosmetics baron Max Factor,2 had been charged with participating in an $8-million stock swindle involving South African diamond-mine securities ($160 million by today’s count). It seemed that Jake had struck a partnership with the king of New York bootleggers, Arnold Rothstein, to stake him $50,000 to set up the swindle. Among Factor’s victims were widows, clergymen, elderly investors, and most significant, members of the British royal family and the chief of Scotland Yard. When the scam was discovered, Factor fled to Monte Carlo, where he quickly created another crime syndicate that successfully broke the casino bank by rigging the tables. Before authorities caught on, Factor had fled once again. In 1931, when the British government located Factor in Al Capone’s Chicago, they commenced extradition proceedings.

Factor was by now a multimillionaire, thanks to the profits from the British and Monte Carlo swindles, and enlisted a strong legal team to stall the federal government for over two years, but by 1933, they had run out of maneuvers. When Curly Humphreys learned that the statute of limitations on the extradition would soon run out, he envisioned his elegant, if elaborate, revenge against Touhy. Only a mind like Curly’s could see the connection.

Factor had been summoned to appear in federal court on April 18, 1933, for what was certain to be his one-way ticket back to England. By amazing coincidence, Jake the Barber’s nineteen-year-old son, Jerome, chose this moment in history to become a kidnapping victim, coincidentally giving Jake an incontestable excuse for having the proceedings postponed yet again. With a $200,000 ransom on Jerome’s head, Chicago police, apparently unaware of Factor’s friendship with Curly, raided the headquarters of the the best kidnappers in Chicago, the Outfit. There they encountered Curly Humphreys, Joe Accardo, and Sam “Golf Bag” Hunt. The gangsters were incredulous, telling the cops that they were in fact strategizing on how to get the young boy freed. Jake himself admitted that he went to Curly for help. After all, Curly was not only Chicago’s best kidnapper, but also one of its best negotiators.

Eight days later, Jake and a carload of Outfitters rescued Jerome on the city’s West Side, but they failed to catch the kidnappers. “We spotted them in their car,” the Barber recounted, “but some policemen came along and the criminals sped away.” Neither Jerome, who was allegedly blindfolded the entire time, nor Jake could identify the scoundrels. With Jake’s legal confrontation in D.C. temporarily postponed, phase one of Curly’s plan was complete.

On May 29, frustrated Supreme Court officials reset the date for Factor’s hearing. It was a last-ditch motion, since the statute was due to expire in early July. But by a propitious turn of events, this time Jake Factor himself turned up kidnapped.

On June 30, 1933, Jake Factor disappeared after leaving an Outfit-controlled saloon in the northwest suburbs. Twelve days later he surfaced, walking the streets of suburban La Grange, appearing bleary-eyed and bearded. He told a policeman he had paid $70,000 in ransom to his kidnappers, whom he could not identify. But the totality of Factor’s physical appearance invited skepticism. As later described by the detaining patrolman, Bernard Gerard: “Well, his tie was in place . . . and he was wearing a light linen suit, which was clean. His sleeves were wrinkled. His pants were somewhat wrinkled. His shoes were quite clean, no marks or dirt on them; no marks of dirt on his hands. He also had a white handkerchief, which was very clean - wrinkled, but no marks of dirt on it. His nails and hands were perfectly clean, cleaner than mine, and I have just cleaned them . . . The cuffs of his shirt were pressed and clean. His collar was straight [and] in place.”

But the discrepancies didn’t matter to a state’s attorney’s office controlled by Curly and the Outfit. Touhy was soon named the chief and only suspect in the case. Many years later, mob-fighting federal judge John P. Barnes described the arrangement between the Outfit and a compliant state’s attorney’s office: “The [Capone] Syndicate could not operate without the approval of the [state’s attorney’s] office . . . The relationship between the State’s Attorney’s office, under [Tom] Courtney and [Dan] Gilbert, and the Capone Syndicate, was such that during the entire period that Courtney was in office [1932-44], no Syndicate man was ever convicted of a major crime in Cook County.”

In rapid succession, Courtney’s goons arrested Roger Touhy and persuaded the Washington authorities to cancel Factor’s extradition proceedings, now that he was a material witness in a capital case. Touhy was tried twice in the Factor case, the first jury unable to reach a decision. Although Factor identified Touhy, his admission was suspect given that he had earlier testified that he had been blindfolded the entire time. Two weeks later, the second trial produced a surprise witness, Isaac Costner, or Tennessee Ike, who, when asked under oath to state his occupation, replied, “Thief.” Ike stated that he was with Touhy during the kidnapping but he was against the idea. Touhy was found guilty this time around and sentenced to ninety-nine years in prison. Meanwhile, Jake the Barber was allowed to stay in the country as “a friend of the court.” Twenty years later, Ike filed a deposition in which he admitted that he was put up to the false testimony by U.S. assistant attorney general Joseph B. Keenan, who promised to cut Ike a break on a thirty-year sentence for mail robbery if he agreed to testify against Touhy. When Keenan reneged, Ike filed the damning deposition.

But it was too little too late for Roger “the Terrible” Touhy, who languished in prison until 1959, when the abomination was finally reversed. When Judge Barnes finally reviewed the case, he concluded that “the kidnapping never took place.” The parole board agreed. Unfortunately for Touhy, he released his autobiography, The Stolen Years, simultaneously with his release from prison, wherein he referred to Curly Humphreys as a pimp.3 Compounding his error, Touhy announced that he intended to sue Factor, State’s Attorney Tom Courtney, Ricca, Humphreys, and Accardo for $300 million for wrongful imprisonment. One wonders what Touhy could have been thinking; it was obvious to many that he was signing his own death warrant. By this time, the Outfit, in collusion with its New York Commission partners, was on the eve of bilking the Teamsters Pension Fund out of hundreds of millions of dollars to finance casino construction in Las Vegas. Touhy’s suit held the ominous potential for exposing this massive conspiracy. Thus it came as no surprise when, on December 16, three weeks after his emancipation, Roger Touhy was murdered with five shotgun blasts, while Jake Factor dined at the Outfit’s Singapore Restaurant. The Daily News reported two days later that “police have been informed that the tough-talking Touhy had given Humphreys . . . this ultimatum: ’Cut me in or you’ll be in trouble. I’ll talk!’ On his deathbed, the former gangster whispered, ’I’ve been expecting it. The bastards never forget.’”

Jake the Barber continued his association with the Outfit for many years. After finally serving six years in prison for mail fraud involving the fraudulent sale of other people’s whiskey receipts, Factor moved on to Las Vegas in the 1950s. At that time, the Outfit had expanded its empire into Sin City, and Curly Humphreys sponsored Jake for a position as manager of one of Vegas’ (and the Outfit’s) first premier hotel-casinos, the Stardust. In 1960, just months after Roger Touhy’s release from prison and subsequent murder, Factor sold Curly Humphreys four hundred shares of First National Life Insurance stock at $20 a share, then bought them back after a few months for $125 per share. Curly netted a tidy $42,000 profit.

In the 1950s, Factor began drawing on the great fortune he had amassed during his early British stock swindle, to embark on a successful PR campaign aimed at creating the persona of Jake the Philanthropist. His frequent six-figure donations to various charities earned him numerous humanitarian awards. Some have asserted that another reason for Touhy’s murder was that a free Touhy could easily destroy the Barber’s hard-won reincarnation as the beneficent John Factor.

In 1960, the Immigration and Naturalization Service (INS) was considering deporting Factor back to England to face the massive mail-fraud charges brought against him decades earlier. Also in 1960, Jake Factor contributed $22,000 to the presidential campaign of Joseph Kennedy’s son Jack, becoming JFK’s single largest campaign contributor. In 1962, the INS moved to deport Factor, but was thwarted when Attorney General Bobby Kennedy brought Factor to Washington to speak with him and review the INS case. Factor later told the press that Bobby Kennedy slyly brought up that he needed donations to help secure the release of 1,113 Cuban Brigade soldiers captured by Castro’s forces after the disastrous April 1961 Bay of Pigs invasion. Reports had been circulating for months that Bobby Kennedy was placing threatening calls to business leaders with tax or other pending legal matters, practically extorting the funds from them. In conversations monitored by the FBI, the Outfit was clearly impressed by Kennedy’s mastering of the “velvet hammer” extortion approach. On one occasion, the agents reported that Giancana aide Chuckie English “pointed out that the attorney general raising money for the Cuba invaders makes Chicago’s Syndicate look like amateurs.” After a number of meetings with the Barber in December 1962, Bobby Kennedy recommended to his brother that Factor be pardoned. Factor told reporters that he had contributed $25,000 to Kennedy’s “Tractors for Cuba” fund.4 President Kennedy granted Jake’s parole on Christmas Eve, 1962, the same night the prisoners landed in Miami, and just one week after the INS had announced its decision to deport Factor.

But soon after, the inexperienced attorney general began to have misgivings about what he had done. Jack Clarke, who worked in the investigative police unit of Chicago’s Mayor Daley, recently recalled what happened next. “Bobby Kennedy called me and asked if there would be any problem if Jake Factor were pardoned. When I explained the details of Factor’s Outfit background - Capone, Humphreys, the Sands, et cetera Bobby went, ’Holy shit!’ He then explained that he had already approved the pardon.” Clarke adds that Bobby’s dealings with the Factor case were not atypical. “RFK didn’t know what he was doing in the Justice Department. He had no idea of the subtleties, the histories of these people.”

It is impossible to know if Bobby Kennedy grasped the historic and complex relationship between the upperworld barons, such as his own father, and the hoods with whom the barons consorted. If he did, he may have thought twice before launching his full-scale assault on the underworld.

Eventually settling in Los Angeles, the much traveled Factor took particular interest in the welfare of underprivileged black youth in the Los Angeles district known as Watts. In the 1960s, after bestowing a million-dollar endowment (allegedly through the Joseph P. Kennedy Foundation) on a Watts youth center, a Los Angeles Times reporter brought up his ties with the Outfit. Factor broke into tears, asking, “How much does a man have to do to bury his past?” The reporter could easily have countered, “Perhaps an apology to Roger Touhy’s family, for starters.”

Factor died of natural causes in 1984 in Beverly Hills. His Los Angeles Times obituary headline read JOHN FACTOR, NOTED PHILANTHROPIST, DIES AFTER LONG ILLNESS.

On June 27, 1933, “the Man” finally caught up with Curly Humphreys and his labor racketeering. Apparently the Milk Wagon Drivers’ Union business manager, Steve Sumner, was not intimidated by the Humphreys muscle. Although Sumner could not prove who actually snagged his partner, Doc Fitchie, he was certain who collected the $50,000 ransom: Curly Humphreys. Without a witness to the actual kidnapping, the court found itself in a quandary and was forced to indict Humphreys on the only charge that seemed to stick in 1930s Chicago: federal tax charges. Thus Humphreys earned the distinction of becoming the only man known to have been charged with not paying taxes on a ransom he received for a kidnapping of which he was never accused.

Instead of answering the charge, Humphreys took the opportunity to pursue one of his favorite hobbies: traveling. After hiring a manager to look after his affairs at the “Century of Progress,” Curly fled the Windy City, “lamming it,” as he put it, for sixteen months. This period gave the first hints of trouble in the Humphreys’ marriage. According to conversations overheard by FBI bugs planted years later, Humphreys spoke of how he was accompanied by “a little blonde I used to have” on his escape. Among other locales visited by Curly and his mistress was Mexico, where Humphreys pursued his passions for fishing, reading, and photography. In future years, Curly expanded into documentary filmmaking.5 The Chicago Crime Commission quickly named Curly its new Public Enemy Number One. In its previous list of twenty-eight hoods, the Commission had failed to even name Humphreys, who now leapfrogged the competition to gain the top spot.

Returning to Chicago some fifteen months later, Humphreys pled guilty to the tax charge, adding that he alone was responsible for the financial misunderstanding. His performance as a “stand-up guy” succeeded in securing the release of others who had participated in the scheme. Curly paid his taxes (with interest and penalties) and calmly headed off to Leavenworth Federal Prison on October 31, 1934. Some knowledgeable observers perceived Humphreys’ acquiescence as reminiscent of Capone’s tactical vacation spent in the Philadelphia lockup. That conclusion was bolstered by the grand schemes to be undertaken by Humphreys upon his release from prison fifteen months later. On his departure for jail, Humphreys informed the press: “While I’m down there, I intend to study English and maybe a little geometry.” For Curly, the term college was not a just a cute euphemism.

The Big House was not such a cavalier subject, however, for the gang’s original architect, Al Capone. Initially placed in the overcrowded Atlanta federal penitentiary, Al displayed gallows humor mixed with some sense of optimism. “Uncle Sam got me busted on a bookkeeping rap,” Al told a fellow prisoner. “Ain’t that the best!” He added hopefully, “If I could just go for a walk. If I could just look at buildings again and smell that Lake Michigan, I’d give a million.” Any optimism Capone might have harbored was quickly tempered by the awful truth of his current situation. Soon after arriving in Atlanta, the Big Guy received a triple whammy: he was diagnosed with central-nervous-system syphilis, gonorrhea, and a perforated septum due to chronic cocaine abuse. He was only thirty-three years old.

As Al’s health went downhill, so did his temperament. He became prone to mood swings and long-winded boasting about his accomplishments. He was constantly harassed by some of the nation’s most violent miscreants, who were more than a little jealous of Capone’s previous life. “Where’re the broads and booze now, fat boy?” they taunted. The Big Guy was resented by low-life inmates, who dismissed his soup kitchen endeavors, instead perceiving him as an ostentatious rich bloat. He was practically a white-collar criminal locked up with child rapists. For the most part, the threats led to nothing and evaporated. Capone spent his days in the shoe repair shop and settled in as best he could. Just as Capone seemed to be coming to terms with his plight, his world was rocked by news that presaged Capone’s total descent into hell. In the fall of 1934, Capone was informed that he was being transferred to the penal system’s newly completed monument to sadism: The Rock, aka Alcatraz. This bleak institution, situated on a small island in San Francisco Bay, was already being whispered about in the mess halls of America’s prisons.

Although inmates are prone to exaggeration, there was no way they could inflate the truth of this torture chamber. One prisoner transferred to Alcatraz said, “The buildup makes Alcatraz pretty bad, but the reality is worse.” The prison sat above an abandoned military garrison on a 120foot promontory. Prisoners were housed in single-occupancy, five-by-nine- foot cells, not allowed to communicate with one another, or the guards for that matter. With the exception of cafeteria time, the prisoners were kept in silent confinement. Men were routinely driven over the edge by the boredom alone. Rule infractions landed a prisoner in D Block, or solitary confinement, in which the cells were completely devoid of light, and the prisoners received only bread and water through a slit in the door. This sadistic chamber broke down some men in six minutes, others in a couple days, yet some were kept in for as long as six months, exiting into the light of day clinically insane. One unhinged inmate, assigned to chopping wood on the dock, suddenly began chopping the fingers off his left hand. After removing them all, he begged a guard to amputate his chopping hand.

When Capone got the news of his transfer, he was fully aware of what it meant, as were his prison tormentors. “You’re going to the Rock, Al, have a nice long ride to Alcatraz,” someone teased. Capone exploded in all directions. His cellmate, Red Rudensky, later wrote about the event: “All the fire and hate and strength and torment erupt[ed] suddenly.” Capone let loose a profanity-laced tirade at the guards, attacking them with all his might. “You’ll never take me out of here!” he shouted before flinging himself at a guard, who signaled for help. When it arrived, the Big Guy was thrown into a wall, slumping to the floor unconscious.

Capone had good reason to be frantic over the news. His tenure on the Rock, coupled with his insidious illness, was nothing short of a prolonged nightmare. Initially, Capone’s work assignment was on the bucket brigade, mopping the bathhouse floor, where he earned the nickname The Wop with the Mop. After a year of begging, Capone persuaded the warden to allow him twenty minutes a day to form a band with other prisoners. Al had his family send him top of the line banjos, mandolins, and music charts and he succeeded in teaching himself some rudimentary songs. On drums was “Machine Gun” Kelly, while sax chores were handled by kidnapper Harmon Whaley. The ensemble was disbanded after a violent row erupted during a rehearsal.

After the disbanding, things went quickly downhill for Capone. As in Atlanta, there were factions who hated Capone simply because he was Capone. He was a racketeer businessman imprisoned with two-bit thugs. One Alcatraz clique known as the Texas Cowboys made it their mission to kill the Big Guy. After one of the gang stabbed Capone repeatedly with a scissors from the barber shop, Capone was rushed to the hospital. The offender was given an incredible six months in solitary. Meanwhile Capone’s sexual paresis had spread to his brain, and he became increasingly delusional and disoriented. Physically, he lost his impressive girth, his hairline, and his Italian-olive complexion. After one frightening bout of delirium in 1938, Capone was placed in a mental ward, but it was clearly too late. When Capone got into a disgusting feces-throwing battle with a patient in an adjacent cage, officials knew it was only a matter of time before he would be remanded to his wife’s custody.

In 1935, with Curly, as well as Jake Guzik, now imprisoned, Frank Nitti, Paul Ricca, and Joe Accardo were left to oversee the Outfit’s business. Although Nitti had seniority, it was Ricca, as liaison to the Commission, and Accardo who took charge behind the scenes. Ricca seized the moment and nourished private relationships with Meyer Lansky and Lucky Luciano. Although Nitti was allowed to sit on his leather throne at the Bismark Hotel, the Ricca-Accardo-Humphreys triumvirate created a power fusion that far exceeded Nitti’s own designs. While Ricca’s work was mostly ambassadorial, Accardo’s talents, which differed from Humphreys’, drew him to a racket much more suited to his tough-guy exterior: gambling.

1. The Chicago Crime Commission’s director, Virgil Peterson, described the Fair: “[It] epitomized a new age - an age of steel, electricity, chromium, aluminum, and modernistic architecture. Most of the buildings were completely without windows. Day and night they were illuminated by electricity. At night, colored illumination added to the beauty of the exteriors of the futuristic buildings. The Travel and Transportation Building was a block and a half long. Inside were locomotives, multiple-motored transport planes, and a cross section of an ocean liner.”

2. Max Factor single-handedly reinvented Hollywood’s look with his development of Pan-Cake makeup. Prior to this, stars were painted with vaudeville-style greasepaint. Factor was also the originator of the pouty-lip look and is widely considered the father of the cosmetics industry. When his products went commercial, they dominated stores for decades. Factor, who was immortalized in the Johnny Mercer song “Hooray for Hollywood,” died in 1938.

3. Joe Accardo saw to it, however, that Teamster truckers would refuse to ship the book, and that Chicago bookstores were frightened off from carrying the memoir.

4. It was reported that Factor’s payoff to RFK was an Outfit practical joke: The money came from the skim the gang was taking from Las Vegas casinos, about which more will be seen.

5. Humphreys shot one such epic on location at Alcatraz, sarcastically dubbing the sound track with the popular song “Hail, Hail, the Gang’s All Here.” (His heirs still proudly display examples of Curly’s photographic prowess, including 8mm footage from Hawaii, Europe, Africa, Havana, and Asia.)

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