Born in Chicago, Herbie started working the rackets in the late 1950s. Blitzstein stood at 6 feet and weighed three hundred pounds and sported a goatee and moustache, dressed flamboyantly and drove a 1973 Cadillac Eldorado. It was said he had a close physical resemblance to the Italian opera singer Luciano Pavarotti. He lived at 6720 North Damen Avenue in Rogers Park, Chicago with his third wife, but spent a great deal of time at Felix Alderisio's bar, The Tradewinds in The Patch. He had been a close associate of convicted mob bookmaker Henry Kushner. When he was convicted of bookmaking by the FBI and sent to prison, Herbert took over his clientele along with mob bookmaker's Boodie Cowan, a bookmaker that was suspected of being murdered by Anthony Spilotro. He was later convicted of racket