Feature Articles

June 2002

The Worlds Richest Cop

Tubbo Gilbert, The Mob and The Power of the Press

By John William Tuohy

      Daniel "Tubbo" Gilbert crawled out of a Chicago slum called the Valley and grew to be one of the most politically powerful, and wealthiest lawmen in American history.

      A neglected child, Gilbert went to work as a wagon boy at age 11 at the busy train depot that once dominated the valley's center. An ambitious young man, in 1913 Gilbert ran for, and won, a position as the Secretary of the Baggage and Parcel delivery union, local 725.

      It was an easy win. His opponent withdrew in the middle of the election, on Christmas night, after somebody shot him in the rear end.

      He ruled over the local with brute force, fear and intimidation. During one wildcat strike, called by the membership without his authority Gilbert beat the striker's leader so badly that he was indicted for assault with intent to kill. The indictment, of course, was later suspended with leave to reinstate. However, the records later disappeared from the criminal courts building.

      Gilbert served on the governing council of the very mobbed up Chicago Teamsters Union until 1917, when he was appointed, through political clout, to the Chicago Police force on April 6, the day the United States entered the First World War.

      While on the force, Gilbert pursued a separate career in union politics, keeping his position as the secretary treasurer of local 725.

      On the force, Tubbo earned a reputation as a brutal, thick necked cop, who was smart enough to surround himself with more capable and brighter underlings.

      He also engaged openly in city politics, and, before long, Gilbert was a political power in Cook County. As a result, his rise in the police department was unprecedented. After serving less then five years as a patrolman, he was promoted to the rank of sergeant and a year later he became a lieutenant. By 1926 he was a captain, and, from 1931 until December 5, 1932, he held the rank of supervising captain, when he was promoted to the States Attorney, or the District Attorney's, chief investigator, a position he held for eighteen years.

      Most people in Chicago thought that it was only a matter of time before he was appointed chief of police.

      As the states attorney's office, chief investigator, Gilbert was the head of his own private police force, which would eventually number over one hundred seasoned investigators, and, as he did in the unions, Tubbo ruled over his department with an iron fist.

      Once, during a city wide election, Tubbo learned that one of his investigators was a spy for Mayor Edward J. Kelly's camp. Tubbo took the cop into his office, locked the door, and beat the man senseless with his fists.

      Charges were filed, but again they were dropped, and all records concerning the charge, disappeared. Around 1930, Tubbo needed money to finance his political ambitions and, as a result, he called a press conference and announced that the States Attorney would "look into the internal workings of the city's unions and clean that business up."

      Critics quickly noted that he never said he would close it down.

      In November of 1936, Tubbo was questioned about his role in helping the Chicago Teamsters, still under the mobs control at that point, fix milk retail prices in Chicago.

      The scandal also involved Dr. Herman Bundesen of the Chicago Board of Health, and officials of local 753 of the milk driver union. All of them, the indictment read, conspired to fix the amount of milk delivered in the city to squeeze out the smaller guys.

      States Attorney Thomas Courtney, who had high political ambitions of his own, refused to allow Tubbo to resign over the scandal, or even to request his resignation, telling the press: "If many people feel that politics has entered into this," Courtney said, "then I won't disagree with that conclusion." Of course, Gilbert and Courtney were close.

      Once, in 1935, they were both accused of using the States Attorney's Office to selectively harass a political leader named Harry Perry, who was also a city Alderman.

      Perry had stated publicly that he feared for his life, and, on March 24, 1935, after Perry had filed a formal complaint against Courtney and Gilbert, he was driving home from a political rally on the South side under the protection of two Chicago police detectives. Suddenly, a dark sedan pulled up alongside Perry's car and a pistol fired from the back seat let off eight rounds into Perry's car which swerved out of control and crashed.

      Remarkably, no one was hurt but Perry withdrew his complaint against Gilbert and Courtney the next morning.

      In April of 1935, the mob almost had its own police chief, when Gilbert

      temporarily left his job in the States Attorney's Office to take another job in the department, as commander of the uniformed patrol. This position placed him one step behind the chief of police. Interestingly enough, this job also placed Gilbert over the vice and gambling units. Nevertheless, in July of 1935, Gilbert stepped down from the uniform position and returned to the chief investigator's post after disbanding the gambling squad.

      The fact that Gilbert was a mob flunky was reaffirmed in May of 1939, when Gilbert was seen, over a three-day weekend, at the Arlington Hotel in Hot Springs, Arkansas, with Frank Nitti. They were spotted in the hotel's bar, and on the links, where Gilbert used gold-plated golf clubs that Nitti had given him as a present.

      During all this time, Gilbert remained in the union business. By the fall of 1938, Gilbert controlled at least seven unions. He dictated who would, or would not, hold office, and, obtaining Gilbert's approval was essential before union leaders began organizing drives. When labor leaders conducted business without him, Gilbert never hesitated to have them arrested.

      Before the 1948 election, both candidates for the states attorney position were asked if they would keep Gilbert on if they won, and both said they would fire him.

      But, the contest winner, John Boyle, reneged, and said that he would only fire Gilbert on Mayor Kennelly's directive. That directive, of course, never came.

      By 1950, most Chicago crime reporters considered William "Tubbo" Gilbert, now a Captain, not only to be the political boss of the Chicago Police Department, but also a full-fledged member of the Chicago crime syndicate, answering directly to Murray Humpreys.

      However, Gilbert's career took a turn for the worse after he was nominated to be Cook County Sheriff, and was widely considered a shoo-in for the post.

      The major issue in Gilbert's campaign was gambling, and Gilbert swore, that if elected, he would close down all of the illegal gambling in Cook County within six months.

      The Chicago Tribune, which had opposed Gilbert's nomination from the start, published papers it had stored away since 1941, papers which Jake Guzak, the mob's money man, had accidentally left in an oven when he moved out of an apartment.

      Those records summarized the profits and loss of the gambling for the mob for one month and they said that under the monthly payoffs "Tub ... $4,000." Gilbert denied the charges by explaining that his friends called him "Tubbo" and not Tub, so, by his logic, it couldn't have been him.

      The newspapers, television and radio covered Gilbert's ties to organized crime, but the voters didn't seem to be listening. Tubbo Gilbert would win the election, hands down.

      Then Gilbert's name came up during the Chicago hearings of the Kefauver Committee, and Tubbo was requested to testify before the committee. Ray Brennan, a renowned Chicago crime reporter said: "What Happened to make Dan Gilbert testify before the Kefauver committee was that Rudy Halley, Chief counsel and some other senate committee people were at the Morrison hotel the night before the Chicago hearings opened. Halley telephoned Gilbert at home after talking in private with Kefauver. Kefauver, a politically ambitious democrat, was aghast at the peril of annoying the all powerful Chicago democratic organization. Halley told Gilbert by phone, in effect 'you are invited to testify at tomorrow's hearings. You are not under a subpoena. You may accept this invitation, or you may decline.' Of course Gilbert declined.

      "I listened in on the conversation on an extension phone without Halley's knowledge. As a result we carried a page one story and banner headlines saying Gilbert was afraid to testify. Dan couldn't stand the heat from the Sun Times. He made a deal with the committee."

      Dan Gilbert testified, for two hours, but his testimony was behind locked doors, a most unusual thing and the transcript was impounded.

      Since it was just before the election and Kefauver was a good democrat, he agreed to the terms that Tubbo Gilbert had set up.

      They questioned Gilbert for two hours behind closed doors. When it was over, Estes Kefauver gave a briefing that left "more questions then answers." Brennan tried everything he could to find out what had happened behind those closed doors, but was unsuccessful. He had more or less given up, and had retired to Nick's Bar for a drink "when inspiration struck."

      Brennan flew to Washington, learned the location of the committee stenographic service, and then, posing as a Senate staff member, he dropped by the service "to pick up a copy of some guy's testimony."

      Remarkably, he was handed a complete copy of Gilbert's testimony. Reading the testimony over in a Senate bathroom, Brennan found out that Gilbert acknowledged the charges of assault, with intent with intent to kill, against him in the 1940 election, leveled by Judge Oscar F. Nelson, who was running for the states attorney's office against Courtney. The indictment was suspended and later disappeared from the police and court records.

      Gilbert said that it was true that his records from the police department were missing, and that he found that "suspect" and that he was a frequent guest of gangster Owney Madden in Hot springs.

      Gilbert also admitted that, while he was in office, justice in the states attorney office was on a "cash and carry basis."

      Gilbert, whose wealth was estimated to be in the millions by the newspapers, told the committee the right figure was around $300,000. He said most of the money came from trading on the speculation market where he was once listed as the biggest trader on the Chicago grain market.

      He admitted owning hundreds of thousands of bushels of wheat, which would eventually lead to his being hauled in for questioning, the federal government looking into manipulation of the grain on the Chicago Board of Trade.

      Gilbert also admitted that he owned 18,000 shares of Royal Crown Cola, extensive utility holdings, and to being "a gambler at heart" who gambled illegally while enforcing the law.

      The testimony also included Gilbert's income tax records which showed that he earned $7,310 in 1948 by wagering on football, baseball and prize fights and elections.

      When questioned about that, Gilbert bragged that the 1933 elections alone he made a $12,000 bet on Roosevelt and he boasted to the committee that he had bet on and won every election since 1921.

      When asked where he placed his bets Gilbert named a gambling joint owned by John Mcdonald at 215 North LaSalle Street.

      "That is not legal, betting, is it Captain Gilbert?" a committee member asked.

      "Well, no, it is not legal, no," Gilbert lied to the panel of lawyers.

      He also admitted that he had gambled in mob locations and that he gambled on everything and anything, baseball, football and even elections. The Kefauver committee secretly concluded that Tubbo Gilbert's administration as Chicago's top cop "was neglect of official duty and shocking indifference to violations of the law."

      The Sun Times printed the testimony, which both fascinated and appalled Cook County voters, who turned out in record numbers to vote against Gilbert. To add insult to injury, Brennan dubbed Gilbert "The World's richest cop" the day before the elections and the name stuck.

      Gilbert's defeat brought down most of the democratic ticket and handed the sheriff office to John "Two Gun" Babb, a Second World War hero who beat Gilbert by 400,000 votes.

      A few days later, Gilbert retired from the force and announced that he would take a position as chief of police at the Arlington & Washington race tracks, where his brother, Maurice, was a lieutenant.

      That was another mistake. Ray Brennan discovered that Maurice Gilbert had been out on sick leave from the Chicago police department since 1948, and had been drawing a steady paycheck from the department and the race track at the same time.

      Gilbert never held a grudge against Brennan for bringing him down, in fact, in one of Tubbo Gilbert's last tirades against the Chicago press he jabbed his finger into a reporter's chest and barked: "All of you's are a pack of rat ... the only one of you's who has any class at all, is Ray Brennan ... and he's a rat too."

      Brennan understood the back-handed compliment.

      President Harry Truman was less forgiving. He threw a fit over the Democrats' beating in Illinois, and Brennan was indicted for posing as a federal official to get Gilbert's testimony, a charge that carried a six-year term.

      The case against him dragged on for three years before the Justice department ruled that he "no criminal intent as we generally understand it."

      After that, Gilbert packed up his millions and moved to California, where he said he planned to open a detective agency in Los Angles, however, a few years later, he suffered a massive heart attack and went into a comfortable semi retirement. He returned to Chicago in the early 1970s, confined to a wheelchair, his legacy forgotten. He died there in 1977.

Mr. Tuohy can be reached by writing to

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