In this episode of Celebrity Blackjack, the cards take strange turns as a player goes from worst to first and a few favorites end up being shut-out. D.L. takes off to an early lead, but when he falls behind with three hands to go, he bets it all and loses. Caroline Rhea develops a weird dynamic with the dealer and an even weirder dynamic with the cards. At first, she just keeps losing and insults everyone from the dealer to D.L. Nearly out of the game, she then bets heavily and wins several hands in a row. The final hand comes down to her vs. Willie Garson, with everyone else out. Although Willie is good gambler, he is so far behind that the result is basically assured. The game ends with a dealer blackjack and Caroline takes home the money for her charity, having smartly bet only $5,000 in her secret final bet.

• William Baldwin
• Steve Harris
• Alex Borstein