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 Party chief, attended the service 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 himself 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." In an appearance a few weeks earlier before a ...

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