“He was part of [Blagojevich’s] inner, inner circle, about as close to the sun as you can get.”

Those days were gone. Now Kelly was holing up on and off in this trailer near 173rd and Cicero. His marriage was on the rocks—he was shacking up in a downtown condo with his girlfriend, Clarissa Flores-Buhelos, a married woman two decades his junior. The feds had indicted him three times in two years; he had pleaded guilty twice, and he was slated to go on trial with his old pal Blagojevich on the third set of charges. A decade or more of prison loomed. In fact, Kelly was expected to turn himself in within a few days. “My life is over,” he had admitted to reporters four days earlier, in a rare unguarded moment before the press.

By Bryan Smith, Chicago Magazine (2010) 

City/Regional Magazine (CRMA) Award nominee