The Outfit

by Gus Russo

  When the bootlegging war with the North Siders reached its bloody St. Valentine’s Day climax in 1929, Curly Humphreys may have played a silent but critical role in its planning. Ostensibly, bootlegging rival Bugs Moran had been targeted by Al Capone, but the death of Weinshank had at least as much effect on the laundry wars as it did on the bootlegging wars. The real target may have been Weinshank, who was killed in the Valentine’s Day bloodbath, not Moran, who was not even present. And the planner may have been Humphreys, not Capone. “The St. Valentine’s Day massacre never really made sense,” asserted Chicago researcher Mike Graham. Graham reasoned that Capone would not have assented to such a suicidal attack, i.e., Capone’s Syndicate could never have weathered the inevitable civic backlash. Graham and others believe that the agenda for the killings is still open to speculation. For some, the Humphreys-Weinshank rivalry is at least as plausible a theory as any other, since Humphreys was the chief beneficiary of the Weinshank murder. Curiously, on Valentine’s Day, 1936, seven years after the massacre, one of its supposed triggermen, Jack McGurn, was gunned down after trying to muscle back into the Outfit. On his body was a sardonic Valentine’s greeting that smacked of Curly Humphrey’s sense of humor:

  You’ve lost your job

  You’ve lost your dough

  Your jewels and handsome houses

  But things could be worse, you know

  You haven’t lost your trousers

  It is not widely known, but McGurn was a scratch golfer who might have turned pro if he had lived. Once, when playing the Western Open in Illinois, the Chicago police “goon squad” was dispatched to the links to harass McGurn, who was in danger of actually winning the event. “You fuckin’ dago,” the cops yelled as McGurn (born Vincenzo Gibaldi) putted on the last four holes.1 Their tactics worked, and Jack “the Duffer” McGurn went in the tank at the end of the round.

  Got Milk?

  By 1931, Curly Humphreys felt confident enough about his racketeering skills to revisit the milk industry, which he had approached without success in 1922. Since his induction into the Syndicate in the midtwenties, Humphreys had been trying to convince Capone to get into the dairy business. Curly saw it as a direct way for the underworld to enter the upperworld: The boys could at last combine wealth with the respectability that accompanied legitimate, upperworld, white-collar scams.

  Curly was his usual convincing self, and according to Chicago journalist and Humphreys’ friend George Murray, Capone began extolling the virtues of milk to his fellows: “Do you guys know there’s a bigger markup in fresh milk than there is in alcohol? Honest to God, we’ve been in the wrong racket all along.” During one prolonged soliloquy, he sounded like an evangelist who had just seen the light: “You gotta have a product that everybody needs every day. We don’t have it in booze. Except for the lushes, most people only buy a couple of fifths of gin or Scotch when they’re having a party. The workingman laps up a half a dozen bottles of beer on Saturday night and that’s it for the week. But with milk! Every family every day wants it on their table. The big people on Lake Shore Drive want thick cream in their coffee. The big families of the yards have to buy a couple of gallons of fresh milk every day for the kids.”

  Although by 1931, Capone was facing serious court battles with the government, he also knew that convicted tax cheats only served a few months prison time, on average. He may have seen his imminent incarceration as a much needed rest, from which he would reemerge as an upperworld milk baron. Curly was given the OK to infiltrate the milk business.

  Humphreys’ experience told him that the quickest way to take over an ongoing upperworld racket was to first gain control of the relevant workers’ unions. His style mandated that force be used only as a last resort: The velvet glove of the payoff was always offered before the hammer of kidnapping. His assault on Local 753 of the Milk Wagon Drivers’ Union began in the late spring of 1931. This powerful union was sitting on a treasury of almost one million dollars. At the time, Robert G. “Old Doc” Fitchie was the local’s president, and Steve Sumner was its business manager. History showed that part of Humphreys’ modus operandi was the use of a trusted partner, such as Fred Evans or Red Barker, in his operations. For the milk operation, he once again teamed with his garage-scam confrere, Red Barker, and a third conspirator, named Frankie Diamond, whose brother was married to Capone’s sister, Mafalda.

  On a spring night in 1931, not long after Capone’s tax indictment, Humphreys and Diamond paid a visit to Steve Sumner. According to later testimony by Sumner, Humphreys took the floor and in his typically charming tones asked Sumner for a favor. “Since 1926,” Curly began, “Capone has been trying to diversify his investments in legitimate business while consolidating his brewing and distilling empire. He is opening a retail dairy business.”

  While Curly initially stated that he was only approaching Sumner as a peace gesture, asking that Sumner refrain from giving Al’s new operation any union troubles, it wasn’t long before Curly got around to the real purpose of his visit: He wanted Local 753 to stake Al’s new business. When Sumner refused; an unhappy Humphreys lowered the boom: “Your union has a million dollars in the treasury. I will hand you a hundred thousand dollars cash. All you have to do is walk away. Leave town. I’ll take over from here.”

  Sumner replied, “That’s out of the question,” and the meeting broke up. Steve Sumner was no fool. He immediately began fortifying both his office and his home in anticipation of the Humphreys bomb squad: bulletproof glass was installed on his car; his headquarters was shielded with sheet-metal plates; bodyguards were employed.

  But Curly Humphreys was no fool either. In December 1931, while Sumner was circling the wagons and Capone was starting his jail term, Curly and Red Barker kidnapped the union’s president, Old Doc Fitchie. In short time the ransom note appeared, demanding $50,000 for Fitchie’s safe release. Sumner immediately caved. “I handed Murray Humphreys fifty thousand dollars cash in December,” Sumner later testified. Fitchie was released unharmed, and two months later Humphreys chartered a new corporation named Meadowmoor Dairies, with an initial capitalization of $50,000. Meadowmoor then had the effrontery to sue fifty-one other unionized dairies to prevent them from forcing Meadowmoor into becoming a union shop. This would allow Meadowmoor a “vendor’s license,” allowing Curly et al. to pay lower wages and hire underage delivery boys, much as newspapers are allowed to employ newsboys. Once Meadowmoor was established, with one C. W. Schaub fronting as president, secretary, and corporate director, the business prospered.

  And though his recent travails were with Humphreys and the underworld, Steve Sumner would later inform an investigating tribunal something it would probably rather not have heard about its own culpability. He testified about the true essence of organized crime in Chicago, and by extension the entire United States: the upperworld. “The racketeering started here in Chicago years ago,” Sumner advised. “It was first brought in by big business. The men whom we generally look to as being above the average were the very men who were the lowest. They brought them [the underworld gangsters] in.” Or, as one veteran Chicago investigator concluded, “The Irish, the Germans, the Poles - they got here first and had already made the move up to judicial corruption and white-collar crime. The Italians were just the last ones here, so they’ll be the last ones out.”

  Much as Capone’s soup kitchens created goodwill among the city’s less fortunate, so too did Meadowmoor have a lasting positive impact on the way milk was bought and sold in the Windy City. Through the Outfit’s representatives in the city council, new rules were adopted that for the first time established a definition of Grade A milk, forbidding lesser grades to be sold within the city limits. Further, the Outfit’s pols gained passage of the city’s first dated-milk ordinance, which established the first guidelines that allowed mothers to protect their children’s health by screening the milk they ingested. Throughout the parliamentary debate over these bills, the upperworld politicians fought hard against the measur
es, which they feared would cripple the established dairies. But the Outfit fought harder and prevailed. Meadowmoor prospered for decades and still exists under the banner of the Richard Martin Milk Company, the name having been changed in 1961, and the present owners are not controlled by the underworld.

  Unmentioned in most gang histories are the benefits that accrued from an association with Curly and the Outfit, not the least of which was protection. Dr. Jay Tischendorf remembers a story told by his grandfather, who drove a horse-drawn milk wagon in the years after Curly Humphreys had taken over the Milk Wagon Drivers’ Union. “My grandfather was robbed at gunpoint by two men who took all that day’s receipts,” Tischendorf says. “My grandfather was distraught. He apologized to his boss, who told him to not worry. The boss said they were not going to the police. Instead they were going to the union.” In one week’s time, the two scoundrels’ bodies were found floating in Lake Michigan.

  Regretfully, not all the Outfit’s racketeering takeovers were as bloodless as the laundry and milk operations. When Humphreys set his sights on Ben Rosenberg’s dry cleaning business, Rosenberg resisted Hum­phreys’ cajoling. Typically, the pressure escalated to Plan B, when Curly dispatched Philip Mangano and Louis Clementi, who spilled acid on clothes in four of Rosenberg’s trucks. When that failed, they beat Rosenberg mercilessly. Then Ben Rosenberg did the unthinkable: Instead of rolling over, he went to the police. When a grand jury returned indictments against Mangano and Clementi, Rosenberg turned up dead, murdered before the case could come to trial.

  Humphreys remained largely unscathed throughout the many years of his labor racketeering. On the few occasions when Humphreys was detained for questioning, he was able to either talk his way out of arrest or pay off the cops before they had time to announce their appearance. On one occasion, a witness to one police confrontation with Humphreys witnessed the payoff king whip out his wallet as soon as he encountered the officers. Proceeding to count out ten $100 bills, Curly asked, “Can’t we settle this right here among friends?” Usually they could.

  Humphreys’ union struggles were only one of the responsibilities he assumed when Big Al “went away.” Given his natural talents, Curly became, most likely by default, the Outfit’s liaison to their political and law enforcement allies. In a tradition going back as far as Chicago’s nineteenth-century bosses, compliant, graft-addled cops and politicians were an integral part of organized crime’s success in Chicago. Hum phreys’ sharp-witted second wife recently described her husband’s modus operandi: “He was buying cops like bananas - by the bunch.” Hum­phreys’ hold over Chicago’s finest became so total that veteran policemen were routinely dismissed for harassing Outfit members. The gang’s Einstein had similar success in the city and state legislatures, where Outfit-controlled pols routinely blocked anticrime bills. When one Illinois governor threatened to pass get-tough laws, the Outfit sent an emissary directly to the governor’s mansion with their proposal. “Drop the crime bills, chief, and we’ll pass the two main planks of your program for you,” offered the gang’s representative. When the chief executive refused to cave in, the Outfit made good on its threat, killing a key bill to establish a state Fair Employment Commission, and a bill calling for a badly needed new state constitutional convention.

  Starting with Capone’s reign the gangsters looked to one politician in particular to advance their interests. His name was Roland V. ’Libby’ Libonati. With Capone’s and the Outfit’s support, Libonati was propelled upward to the state legislature, where he served for twenty-two years, and from there to Washington (1957), where he became “the mob’s congress­man,” installed on the powerful House Judiciary Committee. After all, it was said, the “white collars” had their representatives, why shouldn’t the Outfit?

  Libby developed a colorful persona, and a verbal style that earned him the moniker Mr. Malaprop. Libonati waged a one-man war on the English language with phrases that are remembered in the Windy City to this day: “No one should speak asunder of the governor”; “I am trying not to make any honest mistakes”; “The moss is on the pumpkin”; “Chicago is the aviation crosswords of the world”; “I resent the insinuendoes”; “Chicago will march on to new platitudes of learning”; “. . . for the enlightenment, edification, and hallucination of the alderman from the Fiftieth Ward . . .”; and the unforgettable “walking pedestrians and tantrum bicycles.”

  Libonati, whose attorney brother Eliador also frequently represented Capone, flaunted his role with the Outfit, appearing often in public with the Big Guy himself, even being photographed sitting with Capone and “Machine Gun” Jack McGurn at a Chicago Cubs baseball game. “I was very proud when he [Capone] asked me at the ball game to speak to his son,” Libby later recalled. “Mr Capone showed me great respect as a person of Italian extraction who represented one of the pioneer families in Illinois . . . I treated him with like respect as I would any American. If people treat me nice, I treat them nice.” In 1930, when the Chicago police’s goon squad wanted to round up some of the boys for routine questioning regarding Capone’s whereabouts, they knew right where to go: Libby’s campaign headquarters, where he was celebrating his election to the state legislature. There, according to police reports, they bagged some twenty gangsters “hanging out.” On that occasion, Curly was among those taken in for questioning. Libonati was himself once arrested while in the company of Curly, Paul Ricca, Frankie Rio, and Ralph Pierce. When Frank Nitti was imprisoned in 1931, Libby was a regular visitor. That same year he represented Joe Accardo when Accardo was arrested for a hit. In that instance, counselor Libonati came to the rescue, seeing to it that the indictment was nol-prossed. He did likewise for Paul Ricca years later. Three decades later, Libby’s top aide, Tony Tisci, would become the son-in-law of future boss Sam Giancana.

  For more than four decades Libby and Curly would work together to stall the efforts of the G, especially future attorney general Bobby Kennedy, to prosecute the Outfit.

  Under Curly’s stewardship, and with his wife, Clemi, keeping the books, labor racketeering was perfected, turning a modestly profitable con into a multimillion-dollar operation, with the Outfit controlling as much as 70 percent of the city’s unions. In 1928, the boys were seeing an estimated $10 million a year in profit from Curly’s rackets; by 1931, estimates escalated to over $50 million - small by bootlegging standards, but with unlimited potential, since unlike Volstead, labor was never going to be repealed.

  While the unions were coming under Humphreys’ control, Joe, Paul, and Johnny were quietly laying plans for future conquests with a national scope. However, before the Outfit could put its bold new schemes into motion, a number of temporary hurdles needed to be overcome.

  1. Gibaldi, a talented athlete in many sports, was given the name Jack McGurn by his boxing manager. Irish brawlers, à la Jack Dempsey, were perceived as more marketable at the time.

  3.

  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.