It’s an established truth that the best players in live-bankroll handicapping contests are able to treat the cash they put up like Monopoly money. That was never Joe Pettit. “I have too much respect for the dead presidents to push them all in the middle,” he said. Last Saturday at the Fourstardave Challenge at Saratoga, circumstances conspired in such a way that Pettit was able to take the shot he needed in the end without going all in. In the seventh race, he’d picked up around $10,000 thanks to a successful exacta back-wheel using 29-1 shot Violent Times. After that race, he was in third place, with Roger Cettina $2,000 ahead of him and Dave Nichols $5,000 ahead. Critically, there was also a $4,000 gap back to fourth. “That left me four races to take swings at Dave,” Pettit said, “and I thought that even if I fired and missed, there was still a chance I could hold my position in the tournament and still walk away with plenty on my bankroll.” Throughout the day, Pettit had spoken with a friendly player sitting near him without knowing who the guy was. This happens frequently in contest rooms, where it’s a collegial atmosphere but the handicapping and betting can get in the way of proper introductions. At some point, a camera crew came by to interview his new buddy. Pettit thought he might be the Day 1 winner, but it turned out that the man was Nichols, the very guy he’d been plotting a course to run down. Heading into the last race, the dynamic was the same. Nichols held a $7,000 lead over Pettit, and there was still a $2,000 gap between Pettit and fourth. The nightcap was a short field, off-the-turf race. “Dave must have thought, ‘There isn’t a bet they could make to catch me’ at that point,” Pettit said. Pettit’s top selection in the race was Fancycase, 4-1 through most of the betting. His wife and son watched as he punched a $1,300 exacta 10-1 and played $300 to win on the No. 10. He looked at exacta probables and was hoping to get back enough to take the lead. “I couldn’t believe the crowd gravitated so much toward the 1 and let the 10 go off at that price,” he said. “It was my son’s first visit to Saratoga, and he got a charge out of it,” Pettit said. “By Day 2, he understood the wagering part of it, learning what a box is and all that. Imagine being 13 and having your dad bet a $1,300 exacta? I may have ruined him.” Pettit and Nichols watched the last race together and shared their plays with one another. Fancycase won, but Pettit still thought the results might be close. He’d spaced out for a minute and hadn’t realized that the exacta probables he was looking at before the race were for $1, not $2, so he actually bet twice as much as he needed to. In the end, he had more than enough, finishing with $20,785 in his bankroll, plus more than $50,000 in prize money and a seat at next year’s Belmont Stakes Challenge. It’s very typical for a live-bankroll contest’s winner to be determined by the last race, and this time was no exception. “A lot of times, it’s a one-race rodeo,” Pettit said. “Players sit, sit, sit and go all in at the end.” Now that he’s had the experience of making a push put at the end – even if he did so with the safety net of the cushion between him and fourth place – Pettit feels much more likely to be able to do so again under other circumstances. “I don’t think it’s a coincidence that you see a lot of the same guys always knocking it down in the last race,” he said. “This was a perfect setup for me, but now that I’ve seen it come to fruition, I’m going to be less hesitant to take the big swing.”