Michael Segal

Michael Segal spent nearly eight years behind bars for looting millions of dollars out of his company, Near North Insurance, to pay in part for a lavish lifestyle. Segal was also ordered to pay $842,000 and forfeit to the government his interest in his company and $15 million. And as part of a 2013 settlement, the government kept half of Segal’s $4.175 million interest in the Chicago Bulls — made up of a 1.7-percent limited partnership in the franchise, a 1.1-percent interest in the United Center and a 1.1-percent interest in the team’s broadcasting company. An appeals court found Segal should be allowed to buy back his investment in the Bulls at its appraised value. Segal began his insurance career as a political assistant to 42nd Ward Committeeman George Dunne, who also had a small insurance agency, as many Chicago politicians have for decades. The operation typically worked like this: If you wanted to get anything done in the ward — open a bar, store or restaurant, say — you made sure to buy your insurance from the alderman’s agency. After getting his law degree from DePaul University, Segal decided for good to stay away from elected office and do his business in private. He turned the small Near North Insurance Agency into a powerhouse brokerage with offices in Chicago, Nevada and Los Angeles. Segal happened to be good friends with Mayor Richard M. Daley’s brother, John Daley, who is a Cook County Commissioner and who has earned as much as $400,000 brokering O’Hare Airport contracts, according to a former top executive at Near North. Homer Ryan, the son of former Gov. George H. Ryan, is also a close friend and Near North broker. The elder Ryan was indicted last December by the U.S. Attorney’s Office on charges of racketeering. Segal also reportedly gave premium discounts – which could be illegal under anti-rebating laws – to politically powerful friends such as 42nd Ward Alderman Burton Natarus and ex-con U.S. Rep. Dan Rostenkowski.