Biographies & Memoirs

Part Three

Scandals and Investigations


Playing Politics II: The Truman Connection

By 1945, barely one year into their ten-year term, Paul Ricca and his incarcerated cohorts had reached the end of their patience. Enduring the privations of their Atlanta prison hellhole was bad enough, but doing so while their fellows on the outside lavished in the wire and numbers profits was unbearable. Rubbing salt into their wounds were the early releases, in December 1944, granted to stoolies Willie Bioff and George Browne, both of whom immediately went into hiding. The situation was especially intolerable for the forty-seven-year-old Ricca, who, had he not been pinched for the Hollywood scam, would now be the boss of the Outfit. Thus Ricca made his decision: He and his fellows wanted a quick transfer to Leavenworth, a prelude to an unthinkable early parole.

Ricca initially attempted to obtain the transfer in the traditional way by having his attorney, Edward Monaco, who had brokered Ricca’s Indiana farm purchase, write a letter asking for it. When prison warden Joseph Sanford wrote to the Bureau of Prisons opposing the request, he noted his fears that “money is being paid to obtain the transfer of these men to Leavenworth.” Sanford added that he wanted the Atlanta prisoners sequestered from Nick Circella, who was already at Leavenworth, and kept distanced from their Chicago allies. The Atlanta Parole Board agreed with Sanford and let its federal superiors know it. When he was told of Sanford’s stance and the Atlanta board’s agreement, Ricca was shocked, so unaccustomed was he to having his demands refused. He decided to go over their heads, resorting to a strategy that had always succeeded: He called Chicago. When Ricca got word back to Accardo and the Outfit, the seemingly impossible task predictably fell to the gang’s political mastermind, Curly Humphreys. This would be verified fifteen years later, when the FBI overheard Accardo describing how the events had played out. Curly knew that such an undertaking would require every bit of political leverage he had acquired over the years, and then some. Fortunately for Ricca and the rest, Humphreys had spent the recent past forging alliances with pols whose influence extended even into the Oval Office. After considering the problem, Humphreys hit upon the solution: He would tap a sixty-eight-year-old Missouri attorney named Paul Dillon, a litigator he had employed in 1939 when he’d needed to obtain indictment dismissals for two Outfit thugs named John Nick and Clyde Weston, strong-arms used in the IATSE takeover. Humphreys’ kinship with the Missouri-based Dillon was a natural result of his role as the Outfit’s political liaison to that state. And in the shadowy world of underworld-upperworld collusions, this linkage gave Curly Humphreys leverage over the most powerful politician in the United States.

Truman’s Shadow World

When Curly Humphreys hit upon Paul Dillon as the solution to Ricca’s problems, he did so with the knowledge that Dillon was the St. Louis, Missouri, version of Chicago’s Sid Korshak, with one notable exception: Dillon’s gangster associates in Kansas City, Missouri, had sponsored the ascendancy of the thirty-third president of the United States, Harry S Truman. Humphreys knew that by playing the Kansas City card he was subtly threatening to open a Pandora’s box that Washington would be forced to address. For those like Curly Humphreys who knew the level of corruption in the upperworld, the rules of the game had to be bent. The Missourians were a Capone-like gangster named John Lazia, a Kansas City Democratic boss named Tom Pendergast, and an eager politician named Harry Truman. This triumvirate gave rise to President Truman and his appointees; their subservience to the Chicago Outfit virtually guaranteed that mountains would be moved for Paul Ricca.

Kansas City was known far and wide as Cow Town, since much of the cattle slaughtered in the Chicago stockyards originated from sales in Kansas City’s Livestock Exchange, a 205-acre parcel known as the Kaw, where ten thousand Western cows were sold daily. And the cattle connection to Chicago was merely the beginning. If Chicago was the most corrupt city in the country, Kansas City was a close second, with its municipal police department run by a former Capone gangster. Imported as prohibition muscle from Chicago by the Kansas City machine, ex-con Johnny Lazia quickly rose in the ranks from bootlegger to gambling czar. During Volstead, Lazia kept in regular contact with the Capone Syndicate, which counted Kansas City as one of its bootlegging distribution hubs. On one visit to Chicago, Lazia was officially anointed by Capone as the boss of Kansas City. Lazia mimicked his Chicago superior and alter ego in many ways. Using brute muscle, Lazia controlled not only local politicians, but also the city’s police force. At one point, Lazia forced the Kansas City Police Department to hire sixty ex-cons as cops. A former Kansas City FBI man recently recalled, “If you called the police station, Lazia was more than likely to answer the phone.”

By 1934, 10 percent of the city’s police force had a criminal record. In 1934, a reporter for the New York Herald-Tribune wrote, “If you want excitement with roulette, cards, dice, the races . . . ask a patrolman on the Kansas City streets. He’ll guide you.” One thief recalled, “This town was fast, had good booze joints, plenty of targets, and some of the laziest cops in the country.” During Lazia’s tenure, which lasted until he was murdered in 1934, Kansas City possessed a host of social ills that rivaled those of its Windy City big sister: unsolved kidnappings and murders, rigged elections, and labor sluggings. In 1939, federal judge Albert L. Reeves said, “Kansas City is a seething cauldron of crime, licensed and protected.”

Lazia was allowed to flourish for decades due to his partnership with Democratic boss Tom Pendergast. In a city with a mayor’s office that was legislated to be weakened, ward boss Pendergast thrived. Much as Jake Guzik sat on his throne in Chicago dispensing the Outfit’s largesse to a line of supplicants, so did Pendergast rule from his dingy Main Street office in Kansas City. All morning long (the office only stayed open until noon), Pendergast handed out political favors and city contracts to his subjects. “All right, who’s next?” Pendergast would grumble from his swivel chair and rolltop desk.

Tom Pendergast’s machine mirrored Big Al’s Syndicate in other ways. When his favored pols faced election day, Pendergast’s organization brought in Chicago-like vote sluggers. In the 1936 general election, Pendergast oversaw the posting of more than eighty thousand “ghost” votes. Like Capone with the Sportsman’s Park sideline, Pendergast brought horse racing to Kansas City at his Riverside Park Jockey Club. As Kansas City grew increasingly amoral under Lazia-Pendergast, the predictable vices such as gambling and prostitution took hold, all dancing to the tune of the world-class jazz musicians who gravitated to Kansas City as they did to Chicago. Rising stars included Lester Young, Coleman Hawkins, and arguably the world’s greatest jazz sax player, Charlie Parker, who was born in Kansas City in 1920. “Most of the jazz spots were run by politicians and hoodlums, and the town was wide open for drinking, gambling, and pretty much every form of vice,” pianist Mary Lou Williams remembered.

As his stature grew, Pendergast formed an alliance with the Chicago New York Commission. When he traveled to New York, Pendergast was seen in the company of Lucky Luciano and Frank Costello. He showed up at the infamous 1929 Atlantic City gangster convention and was on hand with the Outfit in Chicago when they and their New York brethren decided to support the presidential candidacy of Franklin Roosevelt. The Kansas City contingent also delivered the vote for FDR. According to IRS investigations, Pendergast delivered 20,687 votes in his First Ward, although the sector only maintained 19,923 registered voters. A local reporter found that one voter had registered forty times, using different names, but the same birth date. When the Lazia-Pendergast alliance was held responsible for a botched hijacking of a federal prisoner in 1933, in which four federal agents were killed, the machine rocketed to the top of the federal authorities’ priority list.

What is most critical in any discussion of corruption in Kansas City is an understanding of the relationship between the Outfit and the Pendergast machine, a relationship that figured into Curly Humphreys’ overall strategy. From the days of Al Capone, the Pendergast-Lazia machine fell under the ultimate control of the Chicago Syndicate, and later, the Outfit. Bill Roemer, an FBI agent in Chicago who would later use hidden microphones to eavesdrop on the Outfit’s most private conversations, summed up what he learned of the Chicago-Kansas City gangster linkage: “The Kansas City mob is a subsidiary of the Chicago mob. Every family of La Cosa Nostra west of Chicago belongs to Chicago . . . the Outfit takes a hunk of their income and oversees their activity.” As his personal representative in Missouri, Curly Humphreys utilized the talents of St. Louis’ Egan Gang muscleman Thomas Whalen. Humphreys also formed Outfit partnerships with St. Louis handbook operator Tony Giardano and racketeer Frank “Buster” Wortman. Authorities noted frequent trips by these men to Chicago, especially Wortman, who became a close personal friend of Humphreys’.

When Johnny Lazia went on trial for tax evasion in 1934, he threatened to “blow the lid” on corruption in Kansas City. Instead, he was murdered on July 10, 1934, gunned down at 3 A.M. as he arrived with his bodyguard at his home. Among the secrets Lazia took to his grave was the connection of Boss Pendergast to the official infrastructure of Kansas City. One of the keys to the survival of the Lazia-Pendergast machine was its sponsorship of county judges who gave them both credibility and a wide berth for their shenanigans. Tom Pendergast and Johnny Lazia, the men who sanctioned election-day beatings, kidnappings, and murders, chose as their main “front” an army pal of Pendergast’s nephew Mike Pendergast. The beneficiary of the machine’s power hailed from Independence, Missouri, a small town just a fewr miles to Kansas City’s northeast. His name was Harry S Truman.

Like the city that fostered his career, Harry Truman was a split personality. A well-liked World War I hero, Truman was, on the one hand, a gregarious, hardworking public servant who was never proved to have been anything but scrupulously honest. These personal attributes, however, confound psychohistorians who attempt to reconcile them with his blind allegiance to friends and sponsors who were among the most corrupt of the era. As his entree to political corruption in 1922, Harry Truman was first given, by Tom Pendergast, the plum role as the machine’s county judge, a position that included many executive responsibilities, such as setting budgets and allocating county contracts. Pendergast’s fixing of the election was so blatant that Truman won by the astonishing count of 137,000 to 9,000. Although Truman’s tenure as judge was highlighted by his hardworking dedication to saving taxpayers’ money, it also included the occasional nod to his patron. In return for Pendergast’s continued support, Truman made what some have called illegal justice-of-the-peace appointments and gave road construction contracts to Pendergast’s shady friends. Truman biographer Richard Lawrence Miller wrote that Truman “not only knew of the machine’s illegalities but participated in some of them.” Truman himself noted that he had looked the other way while his patron plundered the city’s treasury. Between 1930 and 1934, Truman maintained a handwritten journal in which he candidly described how he returned Pendergast’s support. The documents, now residing in the Truman Library, are referred to as the Pickwick Papers, since Truman made the jottings on Pickwick Hotel stationery. “I had to let a former saloon keeper and murderer, a friend of the Big Boss [Pendergast], steal about $10,000 . . . from the general revenues of the County to satisfy my ideal associate,” wrote Truman.

Kansas City old-timers assert that Truman did much more than look the other way. Roger Morris, a prize-winning author and former senior staff member of both Presidents Richard Nixon’s and Lyndon Johnson’s National Security Councils, recently related a family story of growing up in Boss Pendergast’s Kansas City. As a young boy in the late forties, Morris was watching television with his grandmother as President Truman appeared on the screen. “Grandma, it’s the president,” said young Morris. “Oh, that’s just Harry. I could tell you all about him.” Morris eventually learned his grandmother’s story: In the 1920s, the woman had run one of the most successful brothels in Kansas City. Staying in operation obviously entailed payoffs to the Pendergast machine. The man who had picked up the weekly bribe was none other than Harry Truman, Pendergast’s bagman.

After the heat came down on Pendergast-Lazia in the wake of the 1933 massacre that claimed four federal agents, Pendergast decided he needed to boost his influence if he was to survive. He thus decided to elevate his judge, Harry Truman, to the position of U.S. senator. During the ensuing 1934 primaries, in which Pendergast funded Truman for senator, ghost voting was rampant, as was political terrorism; at the height of the electoral frenzy, four political activists were shot dead. When he was asked about vote irregularities in Kansas City in 1934, Truman gave a cynically crafted response: He had nothing to do with Kansas City politics; he voted in Independence.

As senator, Truman consistently turned away those seeking federal relief employment if they bypassed proper channels, i.e., the Pendergast machine, which controlled the local branch of the Works Progress Administration (WPA). To one supplicant Truman curtly replied: “If you will send us endorsements from the Kansas City Democratic Organization, I shall be glad to do what I can for you.” When U.S. Attorney Maurice Milligan announced that he was going to investigate the Pendergast machine’s role in the massive 1936 election fraud, Truman immediately returned to Kansas City and met with Big Boss Pendergast. Soon Truman announced he was going to use his senatorial privilege to block the attorney’s renomination by the full Senate. Only after pressure was exerted by President Roosevelt himself did Truman cease his obstructionism. An infuriated U.S. district judge, Albert Reeves, who was a prime mover in the election investigation, described Senator Truman as “a man who had been nominated by ghost votes, who had been elected with ghost votes, and, if the truth were known, [had] a ghost writer.”

Not only was the underworld aware of Truman’s shady sponsors, but President Roosevelt himself expressed dismay at the collusion. “I told Harry Truman the other day that he better get away from that crowd out there,” Roosevelt told the U.S. attorney from Kansas, Maurice Milligan, in 1939. However, when Pendergast was finally reined in that same year by Milligan and the carnivorous IRS chief Elmer Irey and sentenced to a fifteen-month term, Senator Truman personally called the prison director to ensure Pendergast’s fair treatment. “I want you to know he’s a friend of mine,” implored Senator Truman. “I’m not asking for any favors for him, do you understand, but I wanted him treated no differently from anybody else.” As Truman himself later explained: “I never desert a sinking ship. He was my friend when I needed him, and I will be his.” Elmer Irey responded by calling Truman “a creature of Boss Pendergast.” Pendergast was paroled after one year and died five months later.

Seemingly free of the Big Boss’ legacy, Truman went about the business of the Senate. After Pendergast went away, his empire was taken over by another Chicago-connected gangster, Charles Binaggio, who strengthened alliances with the Outfit and its wire service, the Trans-America. With such powerful allies, Binaggio became, like Pendergast, a fearsome Missouri power broker, with several politicians in his pocket. One of his representatives, state senator Edward J. “Jelly Roll” Hogan, often attended secret Democratic caucuses with the imposing Binaggio sitting at his side.

When Binaggio sought to purchase the gubernatorial election of Forrest Smith, he borrowed $200,000 from the Outfit. Binaggio was believed responsible for the fraud and murders that accompanied the defeat of Truman’s nemesis Roger Slaughter. With Binaggio using the services of Outfit gunmen such as Tony Gizzo, Mooney Giancana began referring to Truman as “our boy.” Curly Humphreys’ daughter, Llewella, then an eight-year-old, recalled that on one of her family’s vacations, her father gave them the grand tour, impressing the youngster with his Capitol Hill connections. “He even knew Harry Truman, and at one time when Mother and I were in Washington, Harry Truman showed us around,” Llewella recalled in 1984. “He became president of the Linked States shortly thereafter.”

Truman: A President the Gangs Could Control

As the 1944 Democratic National Convention loomed conveniently in Chicago, the nation’s pols began positioning themselves to control the all-important vice-presidential nomination: Insiders knew that the failing Roosevelt did not have long to live and that the VP nomination actually amounted to the de facto presidential pick. Since virtually no one supported the current vice president, Henry Wallace, who was deemed too liberal and detached for the job, the jockeying began for pretenders to the throne. The issue was fairly settled, although without Wallace’s knowledge, on June 27, when Democratic National Committee chairman Robert Hannegan told Roosevelt that Wallace had to go. President Roosevelt agreed and soon found himself lobbied not only by upperworld personages, but also by representatives of the underworld. This was still the era of the smoke-filled-room dealmakers, decades before the 1972 primaries wrested some of the nominating power back to the general public. The underworld wanted Pendergast’s boy Harry Truman in the number two slot, against even Truman’s own wishes. According to Truman expert Marquis Childs, Truman was “scared to death” of the nomination, fearful his association with the Big Boss would be dragged out into the light. Truman called the Chicago convention “that miserable time.” But Truman’s own desires mattered little. The underworld wanted a president it could manipulate in a crunch, such as the Ricca parole affair. And one of the key components of the underworld’s Truman putsch was their long association with Roosevelt’s top adviser, labor leader Sidney Hillman.

Sidney Hillman: Labor Statesman with a Secret Life

Forget everything else. The key to Ricca’s parole was the White House. And we held the keys to the White House - we had the Pendergast machine, and we had Sidney.

-A retired Outfit associate

“Labor’s Statesman” Sidney Hillman straddled the moral chasm as deftly as any duplicitous personage in history. A 1907 Russian immigrant to Jim Colosimo’s Chicago, and from there to New York in 1914, Hillman and his wife quickly rose from the garment-worker rank and file to leaders of that industry’s workers’ unions. An icon of the labor movement, Sidney Hillman was president and cofounder of the Congress of Industrial Organizations (CIO). At the time of the 1944 convention, Hillman was Roosevelt’s key labor adviser and a prime influence on FDR’s choice for a running mate. Lionized as a champion of workers’ rights, Hillman was undeniably responsible for improving the plight of America’s workforce, teaming up with Roosevelt to forge such New Deal legislation as the Fair Standards Act. At one point, Hillman was considered the second most powerful man in America. However, Hillman’s secret relationship with the underworld gave the nation’s gangsters a powerful voice in delivering the VP slot to Tom Pendergast’s protege.

Rising up from the bitter struggles of the New York labor movement, Sidney Hillman used the muscle of the Outfit’s Commission partners to fortify his Amalgamated Clothing Workers (ACW) in its violent rise to the top of the New York labor scene. A man described as cocksure, self-absorbed, and relentlessly hateful, Hillman made deals with the devil to force holdout garment manufacturers to recognize his fledgling ACW. In one instance, manufacturer Guido Fererri was murdered days after having a bitter argument with Hillman’s Amalgamated. The prime suspect was labor slugger and kingpin of the Commission’s “Murder, Inc.” Lepke Buchalter, the same Lepke who had participated in the Commission’s formative meetings and had also traveled to Chicago as the New Yorkers’ representative in the Hollywood studio extortion scheme. When Lepke was questioned for the Fererri murder, he called Hillman, who quickly arrived with his attorney, future New York mayor Fiorello La Guardia. Lepke was never charged. In 1941, when Lepke was serving a forty-four-year sentence in Leavenworth for narcotics and racketeering violations, New York DA William O’Dwyer tried to extradite him for the Fererri murder, for which he could have received the electric chair. However, Hillman’s great friend Franklin Roosevelt continually procrastinated in signing the extradition papers. Meanwhile, Pulitzer Prize-winning journalist Westbrook Pegler reported in the New York World-Telegram (syndicated in 121 papers) that Lepke had worked for the ACW when Hillman had ordered the murder of an independent trucker named Joseph Rosen.

Eventually, Lepke was returned to New York, where he was executed for the Rosen hit in 1944, becoming the only gang boss (to this day) to receive that ultimate official sanction. While on death row, Lepke detailed the revelations Hillman had hoped would never come. Buried in the Bureau of Narcotic’s Murder, Inc. files at the New York Archives is a mountain of testimony detailing the relationship between Hillman and Lepke, much of it from the mouth of the imprisoned Lepke. From 1932 to 1937, Hillman paid Lepke $350 per week, with $50 going to the Commission’s Lucky Luciano. For his pay, Lepke terrorized laborers and manufacturers into kowtowing before Hillman’s ACW. Hillman gave Lepke huge bonuses of $25,000 when he successfully broke a strike, and another $25,000 for fixing a murder rap. As for the Fererri murder, Lepke told authorities it was ordered by Hillman. Both the FBI and the Bureau of Narcotics corroborated the Lepke testimony. Harry Anslinger, the thirty-year veteran crime fighter and head of the Bureau of Narcotics concluded, “The facts fitted together too precisely for error.” However, no one was about to go after the second most powerful man in America.

Truman on the 1944 Ticket

On Monday, July 17, 1944, killer Lepke’s sometime employer Sidney Hillman called FDR’s train from his suite at Chicago’s Stevens Hotel. Along with Robert Hannegan, Hillman argued for Truman’s recruitment. FDR agreed. The next day, Hillman began massaging the reluctant Truman at a breakfast meeting at the Ambassador East Hotel. Hillman informed Truman that labor could not back Truman’s choice of the White House’s War Mobilization Director Jimmy Byrnes as Roosevelt’s partner. Hillman told Truman, “If it can’t be Wallace, we have a second choice, but it isn’t Byrnes.”

“Who then?” asked Truman.

“I’m looking at him,” answered Hillman.

Hillman’s influence-peddling was backstopped by Outfit-corrupted Chicago mayor Ed Kelly, who also worked behind the scenes in the anti-Wallace clique at the convention. Meeting with FDR, Kelly and the rest made their case for Truman with the sickly president. But it was Sidney Hillman whose opinion mattered most. Arthur Krock of the New York Times reported that when Robert Hannegan asked Roosevelt about potential veep nominees, Roosevelt replied, “Clear it with Sidney.”

The last person to fall into line was Truman himself. After two days of waiting for the recalcitrant Truman to agree, Roosevelt lost his patience, slamming down the phone on Hannegan when the party sachem reported that Truman was still balking. Roosevelt then employed a strategy later utilized by President Lyndon Johnson, who in 1963 pressured Chief Justice Earl Warren to head up the investigation of the assassination of President John F. Kennedy. On that tragic occasion, Warren demurred from the appointment, citing among other things his heavy workload at the Supreme Court and the “separation of powers” precept of the Constitution. Johnson then made an appeal that Warren could not refuse, telling Warren that only his imprimatur could prevent a Cold War conflagration. “Why, if Khrushchev moved on us, he could kill thirty-nine million in an hour,” Johnson exhorted. “I’m asking you something and you’re saying no to everybody when you could be speaking for thirty-nine million people.” After Warren wiped the tears from his eyes, he said, “I just can’t say no.” Roosevelt was no less insidious, telling Hannegan to relay a message to Truman. “You tell him if he wants to break up the Democratic Party in the middle of a war, that’s his responsibility.” To which Truman replied, “Well, if that is the situation, I’ll have to say yes, but why the hell didn’t he tell me in the first place?’1

Mooney Giancana was among many inside and outside the Outfit who believed that Truman’s links to Kansas City bosses and to FDR’s key New Deal adviser Sidney Hillman had guaranteed his placement on the 1944 ticket. The hidden agendas behind Truman’s selection, referred to as the Second Missouri Compromise, did not go unnoticed by the upperworld either. A dismayed Interior Secretary Harold Ickes was moved to write: “I react strongly against the method of his nomination and the seeming dominating position that the corrupt city bosses now have in the Democratic National organization.2 Eleanor Roosevelt wrote to the disappointed Henry Wallace, “It looks to me as though the bosses had functioned pretty smoothly.” The Chicago Tribune was the most vitriolic when it editorialized: “[We] are faced with the grinning skeleton of Truman the bankrupt, Truman the pliant tool of Boss Pendergast in looting Kansas City’s country government, Truman the yes-man and apologist in the Senate for political gangsters.”

As president, Truman appeared on the surface to have severed his ties to the Pendergast machine. A closer inspection of the record, however, gives a different reading. In 1946, Truman declared war on Congressman Roger Slaughter, a Republican contrarian who consistently opposed Truman’s legislative initiatives. To counteract Slaughter, Truman sought help from his old Kansas City backers, but by this time, Tom Pendergast was deceased. President Truman therefore placed a call to Tom’s nephew and successor as boss, Jim Pendergast, himself a frequent weekend guest of Truman’s at the White House. As a result of Jim’s interference in the next primary, Slaughter was defeated. The Kansas City Star uncovered evidence that the Pendergast-Truman machine had rigged the nomination process. During a subsequent inquiry, a female election watcher was shot to death on her front porch and the fraudulent ballots were destroyed in a City Hall safe that was blown up by dynamite.

When Congress hinted at an investigation of the Kansas City election fixing, Attorney General Tom Clark, about whom much more will be seen, assured the legislature that he had conducted a thorough investigation and that no facts supported the fraud allegations (although it later surfaced that Clark had not even read a 355-page FBI report on the election before he had cut off the probe.) However, a Kansas City grand jury concluded otherwise and indicted seventy-one vote sluggers, and the Kansas City Starconducted its own investigation and also found massive vote fraud, including many voters who had showed up at the polls only to learn they had already voted. Thus despite Clark’s pronouncements, Congress proceeded with its inquiry, and when Tom Clark came under fire from the committee chairman, he responded by saying that if he had conducted a full investigation “no one would be ruined except the Democratic Party.” The candid response prompted the chairman to retort, “And you are one of them. This was a family affair.”

Maurice M. Milligan, the U.S. attorney who had prosecuted Pendergast, wrote that “Harry S Truman’s career, without the help of Boss Pendergast, would have ended far short of the White House.” Milligan summed up the career of Truman thus: ’When the Senator became Vice-President in 1944, the political stock of the renascent Pendergast machine boomed, but it was nothing compared with the golden opportunities that came on Mr. Truman’s succession to the Presidency. New offices, vacancies and resignations which were within the gift of the President, all kinds of Federal patronage found grateful acceptance in the ranks of good machine men, all friends of the President.’

And Pendergast’s nemesis, Maurice Milligan, was promptly relieved of duty by the new president, who appointed a new U.S. attorney to the region. The dismissal came not before Truman’s friends concocted a nefarious scheme to manipulate Milligan to their own ends. When Truman’s Senate reelection bid had come up in 1940, it was widely assumed he would be beaten by the “good government” candidate, Missouri governor Stark. Truman’s people believed that their only hope was to persuade a third candidate, a sure-loser type, that he could actually win, convince him to run, thus splitting the good-government vote with Stark. Realizing that Milligan, a dull bureaucrat and lousy public speaker, was considering a run for the Senate, one of Truman’s closest friends, Tom Evans, paid a visit to Milligan’s brother to put in the fix. Evans convinced the naive Milligans that his intention was pure and that he firmly believed Milligan could be victorious. And to show his conviction, he handed Milligan a $500 campaign contribution. Truman wrote to his wife that if both Stark and Milligan ran, “that would be too good.” As planned, Milligan and Stark nullified each other while Truman snuck through with only a plurality of the vote. Truman historian Robert H. Ferrell wrote: “Truman could not have been renominated without the entrance of Milligan.”

By any measure, Truman’s presidency was as mixed as his personal ethos. To his admirers, he defeated the Japanese and Germans in World War II, established the state of Israel, and organized NATO. To his detractors, Truman was morally culpable not just for his Missouri compromises, but for the decision to drop an atomic bomb on the population of Nagasaki, after he had already done so on Hiroshima; his formation of NATO was a prime reason Soviet-U.S. relations chilled, leading to the costly and dangerous Cold War; he unnecessarily committed U.S. troops to Korea, fifty thousand of whom returned in body bags. Of Truman’s enigmatic moral code, Richard Lawrence Miller wrote, “Truman loved politics, but he held democracy in contempt . . . [He] would always act insensitively about terrors committed by his political allies in Jackson County . . . He had no patience for anyone, great or small, who felt honesty and public service more important than aid to the Pendergast organization . . . Was Truman really indifferent, or could he just not bear to think about his role and responsibility?”

The Transfer

By the time Truman walked away from a presidential reelection bid in 1952, he was dogged by scandalous accusations, not the least of which concerned his possible role in events surrounding Curly Humphreys and the Outfit’s imprisoned Hollywood extortionists. But while Truman was in office, Chicago’s Outfit was little concerned with debating his historical legacy. For the gangsters, all that mattered was that his past rendered him impotent in the face of pressure from America’s empire of crime.

Fully knowledgeable of Truman’s vulnerabilities, Curly Humphreys placed a call to Pendergast’s legal mouthpiece in St. Louis, attorney Paul Dillon. For years, Dillon was the lawyer of record for Pendergast’s muscleman Johnny Lazia. In 1934 and 1940, Dillon managed (at Pendergast’s request) the St. Louis campaign offices for Harry Truman’s two fraud-filled senatorial elections, with the ’34 contest earning the title “The Bloody Election.” With his friend Harry Truman now president, Dillon had an open door at the White House, one of the rare few able to call on a president unannounced. As an added bonus, Dillon counted among his best friends T. Webber Wilson, chairman of the federal parole board.

Curly next enlisted Edward “Putty Nose” Brady to deliver to Dillon a list of the men he wanted transferred. Years later, when Congress launched a major probe into the transfer, they were denied access to the FBI files that disclosed the Bureau’s plumbing of the Brady connection. When Brady died in 1945, his widow, Helen, was allegedly the recipient of a $20,000 bequest, courtesy of the Outfit, according to a Cicero-based Outfit associate, Willie Heeney, who claimed to have delivered the gift.

Agreeing to take up the Outfit’s case, Dillon traveled east and began peddling his influence. Upon his arrival in Washington, Dillon first visited the assistant director of the Bureau of Prisons, Frank Loveland, to whom he introduced himself as a close friend of the president’s. Loveland allowed Dillon to make his plea, but ultimately denied the attorney’s request. Aware that his Outfit client Paul Ricca would not accept failure, Dillon proceeded up the chain, and on August 8, 1945, the Atlanta inmates, except for Rosselli, were transferred to Leavenworth, over the objections of prison officials. One year later, Johnny Rosselli was transferred to Terre Haute, Indiana. It may never be known exactly whom Dillon leaned on, but buried in documents discovered years later among the Bureau of Prison files is a memo noting that “[Attorney General] Tom Clark would like the subjects transferred to Leavenworth.” According to FBI sources, the gang left nothing to chance in its push to obtain the transfers. Years later “a reliable confidential informant” in Chicago reported that Johnny Rosselli had enlisted a well-known D.C. lobbyist, gambler, and ex-con named Samuel Roy Beard in the cause. The informant reported that “through his connections [Beard] was able to arrange the transfer of Rosselli and his associates.” The Bureau never determined exactly how Beard figured into the parole strategy.

While in Washington, Paul Dillon nurtured his friendship with the parole board chairman, T. Webber Wilson, with whom Dillon shared many social dinners. In two years, this friendship, in combination with Dillon’s other political purchase, would play a pivotal role in the fortunes of the Outfit.

Meanwhile in New York, Johnny Torrio’s Commission suffered a major setback: In February 1946, founding member Charles “Lucky” Luciano was deported to Italy. He had been languishing in New York State’s infamous Dannemora Prison for ten years on white-slavery charges. Luciano’s thirty-to-fifty-year sentence was reduced when he used his underworld connections in both the New York harbor and in Sicily to aid in the World War II Allied effort. Within months, Luciano relocated to Havana, Cuba, from where, according to Curly’s second wife, Jeanne, he made clandestine trips into the United States. “We used to meet him at the Plantation Yacht Club [Plantation Key],” Jeanne recalled. “The boys always threw big ’coming out’ bashes for Lucky at the club.”

Lucky’s removal only served to exacerbate New York’s intramural Mafia squabbles, a proclivity that has haunted them ever since. By contrast, Chicago’s Outfit was more unified and focused than ever, even considering the recent extortion convictions. The power this unity afforded them was soon to be put on display for the rest of the country.

1. Robert Hannegan, castigated by the Missouri press for secretly attempting to steal the state governorship from the 1940 Republican victor, was nonetheless named to head the DNC and the IRS district in Missouri by Senator Truman and was later appointed postmaster general by President Truman.

2. Ickes knew from whence he spoke: He was a former Chicago newsman who was the most influential supporter of 1920s reform mayor William Dever, one of the few Chicago mayors who actually tried to confront Syndicate-influenced political corruption.

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