Former Chicago insurance broker Michael Segal’s sentencing for a federal conviction on 19 counts of fraud and racketeering related to nearly $30 million in missing premium trust funds has been delayed indefinitely.
Segal, former owner and CEO of Near North National Group, was due to be sentenced in March, but the date was rescheduled numerous times, with the most recent date being yesterday.
This time, U.S. District Court Judge Ruben Castillo has delayed the sentencing and ordered a psychiatric evaluation for Segal’s allegedly precarious mental condition. Segal, who has been housed at a federal jail in downtown Chicago since being found guilty in June 2004, has reportedly struggled physically and emotionally. His businesses have been sold off in order to pay fines and compensate his clients, and his wife has filed for divorce.
According to Steve Warmbir of the Chicago Sun-Times, Segal has found himself so distracted while in jail that he requested a stenographer to help keep track of his thoughts on his own sentencing.
Earlier, Segal requested leave from federal prison to treat an alleged scabies condition he’d developed while in jail. He was denied leave because he is considered a flight risk.
No new sentencing date has been set. Segal faces more than 20 years in prison.


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