ESPN’s Kendrick Perkins and The Ringer founder Bill Simmons have a somewhat checkered history.
The pair initially found themselves in a public back-and-forth following the 2025 NBA draft, when Perkins predicted that the Toronto Raptors would finish in the top six of the Eastern Conference standings for the 2025-26 season while covering the event for the Worldwide Leader.
“[The Raptors] took Collin Murray-Boyles, and Perk said they have the pieces [to be] a top-six team in the East,” Simmons said at the time. “And at that point, I started looking for a third ESPN channel, but there were only two covering the draft.”
— Vid Clip Hero (@VidClipHero) June 26, 2025
After Perkins responded with a social media post questioning The Sports Guy’s basketball resume and wondering if he had been drinking before criticizing him, Simmons mocked the video and asked the ESPN analyst if he’d like to wager anything on Toronto’s finish.
I’m 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.
— Bill Simmons (@BillSimmons) June 26, 2025
Perk went on to address things directly on the Road Trippin‘ podcast.
“My problem with you is who the f*ck gave you the keys and said you was the gatekeeper for the game of basketball?” Perkins asked.
The NBA regular season wrapped on Sunday, and to Perkins’ credit, the Raptors finished 5th in the standings, setting up a matchup with the Cleveland Cavaliers in the first round of the NBA playoffs. The ESPN NBA analyst didn’t forget about Simmons’ wager proposition.
“Somebody tell (Bill Simmons) he can just make a donation to my non-profit that’s for the youth in our communities that are less fortunate,” Perk posted on Monday morning.
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 https://t.co/wTpp9b7Mod
— Kendrick Perkins (@KendrickPerkins) April 13, 2026
Perkins’ analysis hasn’t always been well-received, but after a 14-season NBA career, it’s clear he has insights into the game. What’s not clear is whether any official wager was actually agreed to, but a donation to Perkins’ non-profit would be a civil way for Simmons to own this one.
About Qwame Skinner
Qwame Skinner has loved both writing and sports his entire life. In addition to his sports coverage at Comeback Media, Qwame writes novels, and his debut; The First Casualty, an adult fantasy, is out now.