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

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.

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The photo was blurry but unmistakable. Dressed in Western wear, next to a cowboy with a fistful of cash, was one of the most famous players in MLB. The story behind the story of the star athlete competing in a different sport, under a fake name, as told by the man who broke it.

The Secret Rodeo Life of Madison Bumgarner

“DOG GONE” blared the New York Times headline. An interview with the Princeton students who decided to pose as Yale cheerleaders in order to kidnap the famous mascot. Everything was going according to plan. Until the dog almost died.

The Handsome Dan Heist

A fishy triathlon time is met with skepticism. A rival coach’s investigation shines light on how she pulled it off. A furious disinformation campaign to obscure the truth. How and why a middle-aged Ironman competitor cut the course in a race with almost nothing at stake.

The Snowball of Chaos, Julie Miller

In a 2011 college football game between UCLA and Arizona, a man dressed as a referee enters the field of play and whistles the game dead. His goal? To get the ball and score a touchdown... naked. Former U of A student Jacen Lankow reveals how and why he attempted one of the greatest streaks in football history, and explains how to trick the TV networks into covering your moment in the spotlight.

Daddy, Why Is the Ref Getting Naked?

All that glitters is not gold. The 4-time NBA All-Star learned that lesson the hard way, falling victim to a spitting-image impersonator. "He got upset but what can I do?" says Hollywood Johnny Depp about the incident captured by TMZ. And later, a UCLA golfer explains the "Hollywood miracle" the Bruins helped pull off with a young pimple-faced Shia Labeouf.

Wade Boggs and the Kirstie Alley Underwear Bet

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