Image: Mitchell Leff

Bill Simmons lost his wager with Kendrick Perkins after the Toronto Raptors successfully finished as the 5th seed in the Eastern Conference for the 2025–26 season.

The wager originated in June 2025 when Kendrick Perkins predicted on NBA Today that the Raptors would be a top-six team. Simmons mocked the take, calling it “crazy” and stating that Toronto would be nothing more than a “fun place to visit” during the season. He challenged Perkins on X (formerly Twitter) to “wager on it ASAP,” which Perkins accepted

 

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