Beyond the Bike Tour: Is Cashman's Sleepout NYC's Toughest Charity Event?
Podcast: The Carton Show with Craig Carton & Chris McMoniglePublished On: Fri Nov 21 2025
Description: BT & Sal kick off the show by discussing Yankees GM Brian Cashman's annual Covenant House Sleep Out, an amazing charitable commitment to raise awareness for youth homelessness. While giving him immense credit for his decade-plus dedication, Sal wonders if Cashman is secretly dreading the night, comparing it to the physical struggle of Boomer's bike tour. The debate heats up with questions about the logistics of the sleepout: How much security is provided? Does he really sleep all night, or is it a "symbolic" few hours? And what does the GM do when nature calls? Ultimately, the hosts conclude that Cashman's long-standing commitment proves he's a true "scrapper" who doesn't tap out, even on a cold New York night.
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