2.
Honest to God, we’ve been in the wrong racket all along.
-Al Capone to Curly Humphreys, 1930
One of the first enterprises embarked on by Al Capone’s heirs was in fact initiated during the Big Guy’s reign. Local lore holds that soon after his recruitment into the Syndicate, Curly Humphreys explained to Capone how the dreadful state of labor-employer relations could work to the gang’s benefit. Humphreys had once again absorbed the essence of recent American history, churned it around in his cranium for a while, and produced a synthesis that would benefit both him and his gang. It was classic Humphreys, displaying the great foresight that saw him dominate the early years of the Outfit’s reign.
In 1886, when the American Federation of Labor (AFL) was formed, workers began enjoying a period of great success. With improving wages and workplace conditions, laborers finally had a voice to be reckoned with: the union. For four decades, laborers enjoyed the benefits of unionization, until a post-World War I recession ended the party. Throughout the Roaring Twenties, unemployment quietly rose, as wages began dropping. In addition, the corporate world began to employ the same Communist-scare tactics that the anti-ethnic groups had used in proselytizing the virtues of alcohol prohibition. Given the nation’s postwar patriotic fever, Americans were coaxed to equate “workers” and “unions” with Marxist philosophies. Those who remained loyal to the unions were marginalized as Bolsheviks. With labor relations rapidly deteriorating, the workers’ unions seemed impotent against the onslaught of antiunion sentiment.
Union membership thus dropped from a prewar high of four million to two million by the late twenties. Employers now felt emboldened to enforce strikebreaking, blacklisting, and vigilantism in their antilabor fervor. The corporate world appeared to be trying to undo labor’s four decades of success.
Employers lost their advantage when businesses began failing by the thousands. Given the precarious atmosphere, businessmen wanting to remain solvent now desperately sought concessions from the workforce. But with workers already in near revolt and the battle lines long-since drawn, the two sides were locked in a chaotic economic free fall. Both employers and employees needed someone who would understand their plight and advance their interests. And Curly Humphreys saw his next great scam: He would offer to represent both sides, while in reality playing them off against each other as the Outfit robbed them both blind. The added beauty of the plan was that it exemplified a maxim that Humphreys had long since adopted as his personal credo: It is far easier to muscle in on established businesses than to build them from scratch.
Even before Humphreys was recruited by Capone’s Syndicate, the young Einstein of Crime had deduced the potential gains to be had in the operation later called labor racketeering. In 1922, at the tender age of twenty-three, an independent Curly had made a futile attempt to convince the milk drivers’ union to ally with the janitors’ union, giving them more than double the bargaining power with tenement owners. Humphreys was more successful in convincing elevator operators to allow him to extort high-rise dwellers. Curly put a simple proposal to the residents of the upper floors: “No pay, you walk up and down twenty floors every day.” To be sure, Curly Humphreys did not invent labor racketeering, but he was the only Chicago gangster capable of bringing out its full potential. The beauty of Humphreys’ synthesis was that he knew where the real profit was located.
The essential elements of a labor racket consisted of terrorizing small businesses into needing protection (euphemistically called a trade association), for which they paid a percentage of their gross income. Simultaneously, as perfected by Humphreys, the racketeer represented the workers (a union in name only) in their grievances against their employers and their trade associations. It was perhaps the most laughably obvious conflict-of-interest arrangement that has ever existed.
In the Chicago of the 1920s more than two hundred such rackets existed, with names that covered every conceivable business with any income worth extorting: the Concrete Road, Concrete Block, Sewer and Water Pipe Makers and Layers Union; The Jewish Chicken Killers; The Kosher Meat Peddlers’ Association; The Master Photo Finishers; The Newspaper Wagon Drivers and Chauffeurs; The Vulcanizers Union; The Undertakers; The Excavating Contractors; The Master Bakers of the Northwest Side; The Distilled Water Dealers; The Street Sweepers Association; and so on.
Al Capone agreed with Curly’s assessment and began planning phase two of his regime, with Curly Humphreys to have a prominent role. Once Capone gave Curly the go-ahead, the takeovers commenced. Humphreys was prescient enough to know just where to turn for an insider’s education into the labor situation: George “Red” Barker. Barker was a bookkeeper by trade, and an avid reader and scholar. But his intimate knowledge of the labor situation inspired his recruitment by Humphreys and Capone. Through his connections with bankers and financiers, Barker obtained union balance sheets and details of the size of their individual treasuries. With Barker’s advice, Humphreys and Capone decided which unions and associations were ripe for takeover. Barker’s first victory for Capone was in taking over the seat of Local 704’s president, James “Lefty” Lynch, on the Teamsters Joint Council.
Local 704 represented the Coal Teamsters, responsible for much of the fuel deliveries to the lucrative Loop area of downtown. The takeover of such a union would allow Capone’s boys to extort all the hotels and businesses when the bitter cold Chicago winter hit. Lynch had unwisely decided not to step down voluntarily and consequently had both of his legs shot out from under him by Capone’s enforcers. At the next council meeting, his chair was assumed by Barker, with no objections from the other petrified council members. In short time, Barker raided 704’s treasury and transferred virtually the entire bounty into Capone’s bank account. When winter hit, the extortions began, with Capone actually passing on some of the largesse to coal-truck drivers, who received handsome wage increases.
Barker also orchestrated the takeover of the Ushers’ Union. At the time, Chicago utilized thousands of ushers at movie theaters, burlesque houses, ball games, prizefights - virtually any indoor or outdoor event. Typically, Barker not only forced promoters to use his union, he had the businessmen bribe him to underpay his workers. In typical racket style, both sides were played.
Having proved his value, Barker became Curly Humphreys’ right-hand union adviser. Barker’s relationship with Humphreys was not a one-way street, however, as Barker learned the art of “persuasion” at the foot of the didactic master; whenever possible, Curly coaxed and cajoled his targets, explaining how he alone could deliver both the worker and the employer from the throes of underpayment and/or overpayment, depending on whom he was cajoling. When his charm failed, Curly resorted to threats and kidnappings, quickly earning a reputation as Chicago’s premier kidnapper. The abductees were rarely harmed, and although ransom was demanded, the focus of the slugging was the takeover of the organizations.
Curly got his start in big-time labor racketeering when he fixed his crosshairs on a prey that proved surprisingly easy to bag: the Midwest Garage Owners Association (MGOA). At the time the Syndicate began focusing on labor racketeering, David “Cockeyed Mulligan” Albin owned the MGOA, a modestly profitable operation. Curly Humphreys saw a quick and easy way for garage owners, and the Syndicate, to increase their cash flow exponentially. But first Humphreys had to take over the MGOA. That was quickly accomplished when Curly and his partner, George “Red” Barker, paid a visit to Albin.
As was his style, Humphreys attempted to cajole Albin into bringing in the Syndicate as his partner, adding that Albin would be wise to stop attending association meetings; Curly would be MGOA’s new mouthpiece. Albin declined Humphrey and Barker’s overture, and the gang was forced to ratchet up the stakes. One night, Syndicate enforcer Danny Stanton came to Albin with his partners, Smith & Wesson, leaving Albin to agonize over a bullet wound through his foot. Like Lefty Lynch of Local 704, Albin was never again seen at an MGOA meeting, his chair now occupied by Curly Humphreys.
Humphreys had reckoned that if automobile vandalism rose drastically, it would be far easier to convince car owners to garage their vehicles. Therefore, next, a willing group of thugs were enlisted to do the dirty work. For that, Humphreys and Barker turned to the 42 Gang, a group of young toughs from the Maxwell Street area who specialized in just such malevolence. The gang, which consisted of dozens of young boys who revered Ali Baba and the Forty Thieves, adopted their name when they realized they had two more members than Baba’s claque. (One future Outfit boss, Salvatore “Mooney” Giancana, would rise from this gang after a stint as Joe Accardo’s wheelman.)
As per Curly’s plan, the gang spread throughout Chicago, often led by Humphreys himself, wielding ice picks to puncture hundreds of car tires. Soon, a newspaper ad appeared, taken out by Humphreys’ MGOA, offering the union’s secure garages to the troubled car-owning populace. When the MGOA’s business doubled overnight, the Outfit collected not only their monthly association dues, but an additional kickback for each car stored. For their efforts, the 42 Gang would collect 10 percent of the take.
Invariably, some disabled cars were left unrepaired for a time, but Curly had that covered as well. After a few palms greased at City Hall, the MGOA became Chicago’s official car-towing contractor, hauling off the now ticketed vandalized vehicles. Policeman issuing the tags received a five-dollar kickback.
Although Humphreys proceeded to maneuver his way into scores of unions and associations, he was far from fulfilled in his racketeering ambitions. The young schemer quickly realized that there was no real money in associations with such arcane names as the Golf Club Organizers, or the Safe Movers. The real plums were intimately tied to the Windy City’s position as America’s service industry capital, and to the beverage that was in even more demand than booze. Thus the Outfit, under the expert counsel of Curly Humphreys, set their sights on the cleaning industry and the milk business.
The Laundry Wars
Chicago’s hotel industry, to say nothing of its countless brothels, required hundreds of thousands of sheets and towels to be cleaned every day. This, combined with the personal needs of millions of residents and tourists, meant that the revenues of the cleaning business actually rivaled those of bootlegging. At even a few cents per item, simple mathematics demonstrated that the laundry trade was the place to be. With the Outfit’s huge two-faced “protection” fees added on, the profits could be astronomical.
In anticipation of a future career as a laundry kingpin, Curly Humphreys took his first step by acquiring his own laundry businesses. In the case of the Boulevard Cleaners, owner Paddy Berrell was paid an early-retirement buyout of $35,000 to let Curly take over. It is anyone’s guess how Humphreys came to own the long-established Drexel Cleaners, but the acquisitions were brilliant strokes that, like all of Curly’s ventures, served multiple purposes: They gave Curly a “front” job to legitimize his income; and they gave the Syndicate somewhere to practice creative accounting, making moneys disappear and reappear as needed. The in-store book work was handled by Curly’s first wife, Clemi, while Jake Guzik held up his end at the Syndicate headquarters. Humphreys’ second wife, Jeanne Stacy, laughs when recalling a Curly pun that she firmly believes was its first usage: “He used to joke about the money he was hiding at his laundry. He called it ’laundering money.’”
But most important, Humphreys’ ownership of laundries like Drexel and Boulevard gave him a foothold in the industry he would soon engage in a massive hostile takeover. Curly considered it going to school. As a strong believer in adult education, Humphreys knew that to successfully take over the laundry business, he had to first learn the business from the inside. In addition, as a bona fide boss in Capone’s organization and a legitimate member of the dry-cleaning business, Humphreys now possessed a double-barreled arsenal he could use to cajole both the employers’ trade associations and the workers’ unions.
By the time Capone and Humphreys targeted the laundry industry, Walter Crowley was already running the scam for the upperworld. As manager of the Master Cleaners and Dyers Association, Crowley oversaw the terrorizing of hundreds of small neighborhood tailor shops, forcing them to submit to his protection association. The tailor shops were not desired for their minimal “tailoring” profits - sewn buttons and so on but for their role as drop-off points for soiled linens and clothing. These items had to be jobbed out to huge central cleaning facilities, where the profits were infinitely larger. Recalcitrant shops were burglarized and bombed, or acid was thrown on the clothes they had consigned. With many of the little shops in line, Master Cleaners made its first tactical mistake by launching assaults on the holdout shops that had combined to form their own protective association, the Central Cleaning Company. Crowley hired thugs who took brass knuckles to the faces of Central’s drivers; delivery trucks were overturned; clean garments were smeared with oil, and when that failed to work, they were sprinkled with acid. The immediate beneficiaries of all the terrorizing were the hired sluggers, the best of whom could earn a tidy $1,000 a week.
In desperation, Central’s president, Ben Kornick, turned to the North Side gang, led by George “Bugs” Moran, for protection. The North Siders were paid $1,800 per week to have their enforcers ride shotgun on Central’s delivery trucks. Kornick’s strategy succeeded, and Crowley’s Master Cleaners backed down, only to redirect their arsenal at Morris Becker’s operation. It was the beginning of the end for Crowley, and the entree that Humphreys, quietly running Drexel Cleaners, had long awaited.
Between 1910 and 1928, Morris Becker had built the ten largest cleaning and dyeing facilities in Chicago. Crowley’s dream of acquiring total control of the cleaning business necessitated Becker’s compliance. As had been the case with Kornick’s Central Cleaning, Becker’s employees were slugged and robbed, and his facilities bombed. For the coup de grace, Becker’s unionized workers were ordered to strike. Soon, the inevitable occurred when Crowley met with Becker and assured him that his troubles would end immediately after Becker joined Master Cleaners and anteed up a $5,000 “initiation fee.” “We had to go to Walter Crowley,” Becker later recalled to the local news media, “and stand on the carpet and receive our punishment for being born in America and thinking we had some rights as American citizens in a free country.” Not long after showing Crowley the door, Becker was visited by Sam Rubin, Crowley’s strong-arm.
“I’ll tell you something, Becker. You have to raise prices,” Rubin dictated. Crowley’s forces wanted Becker to force a 50 percent price rise, most of which would be siphoned off to Master Cleaners. Becker replied, “The Constitution guarantees me the right to life, liberty, and the pursuit of happiness - and to set my own prices.”
“The hell with the Constitution,” said Rubin. “As far as you are concerned, I am a damned sight bigger than the Constitution.” Again, the demand for $5,000 was leveled. Again, Becker refused. Becker’s actions over the next few days displayed his naivete: He sought relief from Chicago’s corrupted legal system. Becker and his son delivered volumes of specific and corroborated evidence to the state’s attorney’s office. Soon the grand jury brought indictments against fifteen members of the Master Cleaners and Dyers Association. If Becker felt optimistic, he had no knowledge of the similarities of upperworld and underworld crime: The white collars could put in the fix with the best of them.
Master Cleaners wisely retained the services of a litigator famous for legal bombast and melodrama, Clarence Darrow. Perhaps the most famous American trial lawyer of all time, Darrow gained fame for his rhetoric-heavy defense of the downtrodden and underprivileged, as well as his staunch support of the union movement. As a social reformer, he made history in his 1925 defense of John Scopes’ right to teach evolution. But in his zeal to give voice to the voiceless, Darrow also defended murderers. In 1924, Darrow perorated against anti-Semitism while defending the undeniably guilty murderers Nathan Leopold, Jr. and Richard Loeb. In his lifelong support of the union movement, Darrow gained the acquittal of Big Bill Haywood, a union leader charged with murder. That Master Cleaners was a corrupt, strong-arm union did not discourage the seventy-one-year-old Darrow from leading their defense.
As Chicagoans tell it, the fix was in “from top to bottom” for the Master Cleaners’ trial. After an anemic presentation by the prosecutor, and despite a mountain of incriminating evidence, the jury took all of fifteen minutes to acquit Crowley and his colleagues. Morris Becker quickly found the nearest phone booth and asked the operator for the number of the Metropole Hotel. As Becker later recounted, “The police, the state’s attorney, the United States attorney would, or could, do nothing. So, we called a man who could protect us - Al Capone. He did it well.”
Actually, the task was delegated to Curly Humphreys and was just the opening he needed to initiate one of the Outfit’s most lucrative takeovers ever. The very day after the court’s verdict, Morris Becker and five other cleaners met at the Metropole with Capone, Humphreys, Guzik, and two of Capone’s lawyers. An arrangement was reached to form a new corporation, Sanitary Cleaning Shops, Inc. On the board of the new venture, along with five other business owners, was Al Capone. For his participation, Capone was paid $25,000 plus a large percentage of the profits, while Curly received $10,000 per year to act as “arbiter” in labor conflicts. Big Al Capone began telling people, “I’m in the cleaning business.”
INDEPENDENT CLEANERS BOAST GANGSTERS WILL PROTECT WHERE POLICE FAIL ran a local headline. The mere inclusion of Capone’s name on Sanitary’s incorporation papers was all that was needed to end Crowley’s vision of a Master Cleaners dynasty. As Morris Becker later said, “I have no need of the police, of the courts, or the law. I have no need of the Employers Association of Chicago. With Al Capone as my partner, I have the best protection in the world.” When interviewed many years after his retirement, Becker still insisted that the alliance with Capone was the right thing to do, and that Capone was an honest partner who lived up to his end of the bargain. “If I had it to do over again, I would never ask for a more honest partner in any business.”
With Master Cleaners on the run, Humphreys went for the jugular. Sam Rubin and his fellow Master Cleaners thugs began receiving late-night phone calls in which they were warned that their wives would be dipped in acid unless Master Cleaners brought in Curly Humphreys to run the shop. After a few broken arms and blown-up porches, Humphreys was invited into Master Cleaners. He had finally bagged the golden goose, along with its $300,000 treasury nest egg. The grand plan was completed when Humphreys grabbed Local 46 of the Laundry, Cleaners, and Dye House Workers International Union.
In all, some 157 businesses were bombed during the sixteen-month laundry war. It should be noted, however, that when Curly employed the bomb, he made certain that it went off at 5 or 6 A.M., to minimalize the chance of casualties. Predictably, when the ashes had settled, Capone’s Syndicate stood victorious. Although Curly and the Syndicate were now the dominant forces in local laundering, one obstacle remained to total control: Al Weinshank. As a labor racketeer, Weinshank had recently allied with Bugs Moran’s North Siders, who in turn had partnered with Ben Kornick’s Central Cleaning Company. As a criminal version of the Civil War, this contest pitted Weinshank and the North against Humphreys and the South, climaxing with Chicago’s own version of Antietam. In fact, the manner in which this final thorn was removed from Humphrey’s side may have been an overlooked component to one of the nation’s most infamous crimes.
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 measures, 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.