Kendrick Perkins reminds Bill Simmons about Toronto Raptors 'wager'

Almost as soon as the 2025-26 NBA regular season officially ended, Kendrick Perkins made sure everybody knew he kept the receipts for Bill Simmons.

The former NBA player who's now a prominent commentator in ESPN's coverage of the league sent out a reminder via social media at 2:10 a.m. on Monday, April 13, that he was right about the Toronto Raptors and Simmons – the former ESPN personality who founded The Ringer website and podcast network, hosts "The Bill Simmons Podcast," and wrote "The Book of Basketball," – was wrong.

This particular feud between Perkins and Simmons dates back to June 2025 when Perkins posted a video in which he called Simmons a "fool," among other things, after apparent criticism Simmons had levied against Perkins for predicting the Raptors would be a top-six seed in the Eastern Conference during the 2025-26 season. Simmons, at the time, offered to put a "wager" on Perkins' take.

Well, the Raptors will be the No. 5 seed and face the No. 4 seed Cleveland Cavaliers when the Eastern Conference playoffs begin this weekend.

Perkins didn't forget about Simmons' proposition for a bet. It's unclear if either side actually agreed to terms prior to Perkins resurfacing their original back-and-forth on Monday.

"Somebody tell @BillSimmons he can just make a donation to my non profit that’s for the youth in our communities that are less fortunate," Perkins wrote on his X account over the original tweet exchange with Simmons.

Perkins, 41, played 14 seasons in the NBA, including the first eight years of his career with the Boston Celtics. Simmons, 56, is an unabashed Boston sports fan who came to national prominence as a columnist at ESPN beginning in the early 2000s, including a two-year stint as an analyst on ESPN's NBA Countdown show.

"I don't know who anointed you the preacher or king or the head honcho of basketball, of the way things need to be. What have you done? Have you ever played?" Perkins said to Simmons in his initial video posted to social media on June 26, 2025. "... You feel like you're sitting on this throne. You got in your feelings because I feel like the Toronto Raptors are going to be a top-six seed in the Eastern Conference this upcoming season? So? That wasn't a crazy take or anything to that nature. It's a real thing, fool."

Simmons wrote back to Perkins in June he was, "honored that you sat in a car for 2+ minutes to scold me on your iPhone like this, even though we are a combined age of like 92. If you actually think Toronto will be top-6 in the East in anything other than 'most fun place to visit' – let’s wager on it ASAP."

Perkins was ready to collect just as soon as the NBA regular season concluded.