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Betting Highlights
Favorite Bet of All-Time
As a young journalist trying to make a go of it in St. Louis, I placed $10 -- the equivalent of a pitcher of beer -- on a 40/1 shot in the Breeders’ Cup Classic named Volponi that wound up winning by six lengths. There’s nothing quite like jumping up and down in your boxer shorts in front of a black and white television set in a sparsely furnished apartment, that I’ll tell you.
Most Heartbreaking Bet
I bet a lot more than $10 on the 2019 Kentucky Derby. When the horses crossed the wire, I thought I had hit the exacta with one favorite, Maximum Security, and one long shot, Country House. I also had both horses to win and place. That would have been an extremely handsome payout, but Maximum Security infamously got taken down -- and way out of the money -- for creating contact on the far turn. Country House wound up winning as a result, so I still made a tidy profit, but it was the most deflating victorious wager I’d ever experienced.