Big-name NBA analyst loses Toronto Raptors bet and Scottie Barnes wants him to pay up

For a team that won just 30 games last season, many didn’t have the Toronto Raptors making the NBA playoffs on their Bingo card this year, let alone finishing in the top five.

Popular sports podcast host Bill Simmons was so doubtful the Raptors would be in the postseason that he made a wager with former NBA player turned analyst Kendrick Perkins. Now, after Toronto clinched the fifth seed, Raptors All-Star Scottie Barnes is asking the podcaster to pay up.

Last June, Perkins said on NBA Today that he believed the Raptors would finish as a top-six team in the Eastern Conference this season. Simmons fired back on his own show, calling the take "crazy" and saying Toronto would be nothing more than a "fun place to visit" during the 2025-26 season.

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

The two agreed to a wager, and after the Raptors improved their record to 46-36 with a win Sunday over the Brooklyn Nets, Perkins made sure social media knew he kept the receipts.

"Somebody tell [Bill Simmons] he can just make a donation to my non-profit that's for the youth in communities that are less fortunate," Perkins tweeted just hours after Toronto secured a playoff spot.

Simmons has yet to address the bet on his show or social media, but Barnes soon joined the conversation, telling the podcaster to settle up.

Barnes replied to Perkins’ tweet, saying: "send dat asap."

send dat asap!

— Scott Barnes (@ScottBarnes561) April 13, 2026

Perkins, 41, played 14 seasons in the NBA, including the first eight years of his career with the Boston Celtics. Simmons, 56, is an outspoken Boston sports fan who rose to prominence as an NFL and NBA columnist with ESPN, and now hosts one most popular sports podcasts in the U.S.: The Bill Simmons Podcast.

On the most recent episode of Simmons' show, he doubled down on doubting Toronto, saying the Raptors "don't have it in them" to beat the Cavaliers. 

"It would have to be a real collapse, since [Raptors] don't have enough offensive options," he said.

The Raptors’ playoff campaign will begin on Saturday, April 18, on the road against the Cleveland Cavaliers at 1 p.m. EDT.