Tom Brady is always at the Kentucky Derby, usually in full derby-style. According to football writer Chris B. Brown who was at the tracks, it was rumored Brady put $4,700 on Orb this year. Since Orb won, this would leave Brady with about $23,500 in winnings.
There's video of Brady screaming in celebration after Orb won, so we're guessing he definitely won a bunch of money. Brady starts screaming at the 20 second mark (via Big Lead Sports):
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