Kyle, win-win scenario

Mommy’s little boy giving Mom a win.

Joel, letting the addiction win

Andy, often Ava, win-win

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Kline, Keeping His Championship as Cassidy [THEME] [EARNING THE

Mike, currently Mia, not a guaranteed win [Theme] [Bet Gone Wrong]

Challenger #42 of 64, going for the win

Denied the win

Chelsea, Guaranteed Win (CYOA) Part 12

Can't Win for Losing

Andrew, now Alyssa, letting the best man win