A failed attempt at scoring Kirstie Alley's underwear leads the Red Sox third baseman to enlist his mistress in an attempt to win a spring training bet. But when the spurned mistress dishes a tell-all to Playboy magazine, Boggs' deceitful ways are exposed. 

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A failed attempt at scoring Kirstie Alley's underwear leads the Red Sox third baseman to enlist his mistress in an attempt to win a spring training bet. But when the spurned mistress dishes a tell-all to Playboy magazine, Boggs' deceitful ways are exposed.  Learn more about your ad-choices at <a href="https://www.iheartpodcastnetwork.com">https://www.iheartpodcastnetwork.com</a>

Trickeration is a weekly show that breaks down the boldest and craziest acts of deception in sports. Each show will feature interviews with principle participants in these sporty schemes and deep dives into how and why these attempts to unlevel the playing field ultimately succeeded or failed. Sportswriter Matt Waxman investigates tales of grooved pitches, savage hustles, chilling pranks and more.

Trickeration

A failed attempt at scoring Kirstie Alley's underwear leads the Red Sox third baseman to enlist his mistress in an attempt to win a spring training bet. But when the spurned mistress dishes a tell-all to Playboy magazine, Boggs' deceitful ways are exposed.

Wade Boggs and the Kirstie Alley Underwear Bet

https://api.omny.fm/orgs/e73c998e-6e60-432f-8610-ae210140c5b1/clips/8cf41e39-b0fe-4354-867f-ae30018b0e66/transcript