Who was Chicago's Dan Gilbert? 'The world's richest cop'

Dan Gilbert was a big shot, the kind of guy whose name rated boldface type in gossip columns throughout most of his 80 years. His 1970 funeral was a who's who of Chicago's establishment. Mayor Richard J. Daley and Col. Jake Arvey, the local Democratic Partychief, attended the services at Holy Name Cathedral. So, too, did a flock of business and union heavies.
It was a pretty good send-off for "the world's richest cop," as he was called by headline writers. The implication was that he didn't earn the title on a patrolman's salary or even a captain's salary, a rank he attained in a scant nine years on the job. Gilbert attributed his financial success to Lady Luck.
"You see in the press today that I'm a big bad gambler," Gilbert said, according to the Tribune's account of a 1950 political rally. "They say that I bet on football games and elections. Yes I do. And I'll bet on this election too — that I'll be the next state's attorney." Unfortunately, he was running for Cook County sheriff.
He had been even more forthcoming about his finances in an appearance a few weeks earlier before a U.S. Senate committee in Chicago to investigate organized crime. As a courtesy to the Chicago Machine, committee Chairman Estes Kefauver, a Democratic senator with presidential ambitions, heard Gilbert's testimony behind closed doors. "Tubbo," as Gilbert was known to friends and foes, said he was worth $360,000. At the time, he was making $9,000 a year as chief investigator for the Cook County state's attorney. Gilbert attributed the difference between the two amounts to commodities trading and gambling.
Mathematicians and wiseguys say the odds are against a gambler ending up ahead of the game, but Gilbert did make big money in commodities. In 1947, the Tribune reported that Gilbert's name was on a Department of Agriculture list of 100 elected officials "gambling in the wheat market ... when inside knowledge of administration market moves would have enabled a speculator in wheat to reap enormous profits."
Whatever its source, his fortune enabled Gilbert to live on Lake Shore Drive, a world apart from the Valley, the hardscrabble Near West Side neighborhood of his youth. The Valley was a place where police work, crime or union office seemed the best routes out of poverty. Gilbert chose all three. At 23, he was elected secretary-treasurer of a Teamsterslocal, giving him a foothold in union politics that he wasn't about to surrender upon becoming a cop in 1918.
Looking back at his career, George Bliss, the Trib's ace investigative reporter, noted that by 1938, Gilbert controlled seven Teamsters locals. "Union leaders took their problems directly to Gilbert and he was said to have dictated the men he wanted as officers of the locals," Bliss wrote in 1954.
Gilbert had no compunctions about mixing his police authority and union activities. When a 1934 strike of waiters and bartenders closed down the French Casino, which the Tribune observed "featured girls from the Folies Bergeres, in Paris," Gilbert ordered union officials to settle with the club, pronto. "The state's attorney is opposed to unjustified strikes," Gilbert told them, "and as far as I can see, there is no justification for this one." The club's owner controlled the Music Corporation of America, a powerful booking agent of nightclub acts.
The following year, Gilbert forbade a breakaway Teamsters faction to meet, sending cops to block access to the Hod Carriers' Hall, as the Tribune reported. When the insurgents gathered instead at the Bricklayers' Hall, Gilbert waited until the meeting was over, then arrested their leaders.
When John "Jake the Barber" Factor, mobster and half brother of Max Factor, disappeared in 1933, Gilbert had some minor hoodlums rounded up. Saying he suspected they knew something but couldn't prove it, he ordered them to leave town and pointed to an officer. "This man will bring you in feet first if you stay around," Gilbert said, according to the Tribune's account. "You may beat the law, but you can't beat bullets."
When Factor reappeared, just as mysteriously as he disappeared, he said he'd been kidnapped by Roger Touhy, another mobster; Touhy served 25 years before his conviction was overturned by a judge who denounced Gilbert's role in the affair. Finding that Touhy had been railroaded, Judge John Barnes ruled the jury had heard "perjured testimony, which Chief Investigator Gilbert procured and knew to be perjured."
Gilbert was already retired at that point. For decades, he'd been the Teflon cop. He was summoned before grand juries that declined to indict him. Tantalizing clues surfaced but led nowhere. In 1941, the Tribune reported the discovery of mafia financial records in the oven of an apartment formerly occupied by mob boss Jake Guzik. On a page that recorded payoffs for protection was the entry "Tub ... $4,000." Gilbert denied it referred to him, because his friends called him "Tubbo," never "Tub." In 1963, a loose-leaf notebook was found in a desk in the state's attorney's office. Inside were tidbits — names of girlfriends, mob associates, hangouts — of Capone-era hoodlums like "George 'Tony the Wop' Basso," "Thomas (Rubber Nose) Conley" and "'Two Gun' Ike Katsovitch."
"I never saw that book in my life," Gilbert told the Tribune.
By that time, Tubbo's luck was gone. When he ran for sheriff in 1950, he was tripped up by an enterprising reporter. Posing as a newly hired Senate staffer, Sun-Times reporter Ray Brennan conned the sealed transcripts of Gilbert's appearance before the Kefauver committee out of its transcription service. Publication of Gilbert's testimony sank his first, and only, run for public office. After losing by a landslide, he retired as a cop and spent his remaining years shuttling between the West Coast and Chicago, minding his real estate investments and securities portfolio.
Perhaps the proper eulogy for Gilbert, indeed for the whole shabby era, was something Cook County State's Attorney Thomas Courtney reportedly observed in 1936, when Gilbert was accused of conspiring to fix milk prices. Editorial writers and civic-minded citizens were demanding Gilbert be fired, but Courtney declined to do so, saying:
"If many people feel that politics has entered into this, then I won't disagree with that conclusion."