The 40-year-old leader of one of Chicago's most violent street gangs, the Hobos, will learn if he'll spend the rest of his life in prison.

Gregory "Bowlegs" Chester on Thursday will be among the first members of the gang prosecutors call an "all-star team" of criminals to be sentenced.

Federal prosecutors want a life term for a conspiracy that included nine murders. Chester's attorney, Beau Brindley, asked for 20 years.

Chester says it's inconceivable someone with his deformed legs could become gang boss. Prosecutors say others did "his dirty work."

A government filing says Chester attended his trial after swallowing a balloon with drugs a visitor handed him. In an intercepted email, Chester explained he had just $2 and intended to sell the drugs to inmates to pay his lawyer fees.