Lilly and the horse races
Were the races fixed? It seems like she was assigned to place bets on very specific horses. Was the goal to bet on all major long shots just in case they came in? That seems like a losing proposition -- betting huge sums on horses that have little chance of winning, on the premise that the payouts will be smaller on the rare times that one of them does win.
So I'm guessing the races are fixed, and Bobo knows which long shots are going to win.