Gambling is a dangerous pastime, particularly when a bet emerges from a social media argument. Last summer, Bill Simmons guaranteed the Toronto Raptors wouldn't be in the top six in the East. Almost ten months later, Simmons is eating those words, and the Raps are in the playoffs.
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.
— Bill Simmons (@BillSimmons) June 26, 2025
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.
There are a lot of big personalities with bold opinions in the world of sports. Two of the most confident are Bill Simmons and Kendrick Perkins. Both of them have made names for themselves over the years with sometimes controversial takes that garner a lot of attention.
During the offseason in the summer of 2025, Simmons and Big Perk got into a bit of a debate on social media about the Raptors' performance in the upcoming season. Simmons seemed borderline offended by the idea that Toronto would be top six in the Eastern Conference.
To be fair to Simmons, it had been a minute or two since the Raptors were considered contenders. Trading for Brandon InrIngramgram, who spent most of the previous season injured, didn't really help their projections for 2025-2026. There were more than a few people who didn't see the potential.
The Raptors are proving their haters wrong
Unfortunately for Simmons, the season went a different direction than he had thought. While the Raptors had a bit of an up-and-down year, they finished fifth in the East and are in the playoffs for the first time since 2022. It's a huge step for a young team that's gone through some major changes.
Now, Perkins is calling in the bet, saying he would like Simmons to make a donation to a charity of his choosing. While this seems to be put to bed, there is a long-running beef between the two pundits that has manifested as arguments on any number of NBA-related topics.
While that enmity is unlikely to end anytime soon, it's not really what matters. What does matter is that the Raptors did, in fact, make the playoffs this season, which is an incredibly important step for this team. They need postseason experience to figure out how to attack the next level.
Whether pundits believe in the Raptors is irrelevant. The team needs to believe in themselves, their growth as a unit, and what the future holds for them. These playoffs will show the Raptors what they need to be real contenders, giving Simmons and Perkins something new to bet on.
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