One sultry August afternoon I went out to Arlington and put a thousand on a long shot to win the third race. I did crazy things as a matter of routine back then, and when the colt came in by half a length at forty to one, I knew there was a God in heaven and that he was smiling down at my craziness.
The winnings provided me with the clout to do the thing I most wanted to do, and I promptly set out to turn my dream into reality. I requested a private counsel with Bingo Walsh in his penthouse apartment overlooking Lake Michigan. Bingo was right-hand man to Boss O’Malley, who had one of the largest setups in Cook County. Gambling parlours, numbers operations, whorehouses, protection squads, slot machines–Bingo managed all these enterprises with a firm hand, accountable to no one but the boss himself. I was lucky to have him as my mentor.
Once I laid out the plan to him and he got over his initial shock, he grudgingly gave me the green light. It wasn’t that he thought the proposition was unworthy, but I think he was disappointed in me for setting my sights so low. He was grooming me for a place in the inner circle, and here I was telling him that I wanted to go my own way and open a nightclub that would occupy my energies to the exclusion of all else. I could see how he might interpret it as an act of betrayal, and I had to tread carefully around that trap with some fancy footwork. Luckily, my mouth was in good form that evening, and by showing how many advantages would accrue to him in terms of both profit and pleasure, I eventually brought him around.