Chief Wallaby to win the Kentucky Derby (+1000)
“So at the odds, right now he's 10-1 in wagering. I'll take Chief Wallaby in the hopes that he's going to take a step forward”
Golden Tempo won the 152nd Kentucky Derby at Churchill Downs on May 2, 2026; Chief Wallabee finished fourth, so the futures bet on Chief Wallabee to win the Derby lost.
Randomized to win
“I like a horse called Randomized in that race to go wire to wire.”
Raging Sea won the 2025 La Troienne Stakes (G1) at Churchill Downs on May 2, 2025 (Wikipedia), not Randomized, so the win bet loses.
Randomized / Raging Sea / Thorpedo Anna trifecta
“I'll give you a Randomized Raging Sea, Torpedo Anna trifecta.”
The bet requires Randomized to win, Raging Sea to place 2nd, and Thorpedo Anna to place 3rd; Raging Sea actually won the 2025 La Troienne Stakes on May 2, 2025 (Wikipedia), so the trifecta's win position doesn't match and the bet loses.