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Changes are coming for the Toronto Raptors.

Over the next few days, we’ll venture to break down all sides of what’s next for the organization following a disappointing 41-41 season that ended with an abrupt play-in exit against the Chicago Bulls. Toronto has three significant free agents Fred VanVleet, Jakob Poeltl, and Gary Trent Jr. On top of that, both Pascal Siakam and O.G. Anunoby are extension eligible and could be looking for long-term money.

But let’s start at the very top.

Siakam will be eligible for a four or five-year extension this summer contingent on if he earns an All-NBA nod. The safe bet would probably be he doesn’t earn a spot. Depending on where you draw the line for games played, he’s probably seventh or eighth in All-NBA forwards voting, but at least a couple of voters have penciled the 29-year-old down for a third-team spot.

If Siakam does earn a spot, he and the Raptors can agree to a super-max extension of five years, roughly $290 million, based on 35% of the salary cap. Toronto doesn’t necessarily have to offer him the full supermax. Rudy Gobert, for example, was super-max eligible with the Utah Jazz but signed for just less than the full max.

Conversely, should Siakam miss All-NBA, he’d be eligible for a four-year extension at roughly $ 192 million, based on 30% of the salary cap. That number could grow to five years, roughly $249 million should Siakam opt to play out this season and then re-sign with the Raptors when he hits free agency and fail to make All-NBA next season as well.

For now, the season's end is still a little too raw for Siakam to contemplate his future with the team. Finding out if he made an All-NBA team this year is certainly the first step. After that, conversations will need to be had.

“I don’t know what’s gonna happen but obviously this is Year 7 for me being here, this feels like a part of me,” Siakam said Thursday. “It’s probably the most I’ve been somewhere outside of Cameroon and it feels like home. I’d definitely love to be in Toronto and it’s a part of who I am as a person, I feel like they’ve seen me grow and this feels like home.”

Siakam did make it clear Thursday that he wants to win. A long drawn-out rebuild or a rejigging of the roster to take a step back doesn’t seem particularly appealing. This past season took a toll on him and he seems disinterested in doing that again.

“I wanna win, that’s one of the reasons I play the game,” he said. “It brings you joy, it brings you happiness, those years or those times when we have good seasons and we play good basketball and we’re winning, it’s probably the happiest.”

“I feel like it’s better than anything, really,” he added. “You can go out there and make a lot of money but if there’s no joy in doing what you’re doing, what’s the point? I feel like that’s the type of person that I am, winning brings me joy and I wanna make the most money that I can make but I also want to enjoy it.”

At the trade deadline, Siakam made it clear — at least publicly — that he leaves front office decisions to the front office. He’s happy to go out and play basketball and leave the big decisions to others. Unless, he said, his phone starts ringing and it’s him who is on the move.

Considering Toronto’s situation this summer, that might not be out of the question. With three of the Raptors’ six best players heading into free agency and Scottie Barnes borderline untouchable, Toronto’s best way to shake up the roster would be to move on from Siakam or Anunoby. 

If the deadline chatter was any indication of what’s to come, those calls will be had. Siakam is valuable. He may not be a top-15 player in the league, but he’s in that next tier and desperate teams may be willing to pony up for a player who just averaged 24.2 points, 5.8 assists, and 7.8 rebounds per game.

After seven years with the organization, Siakam’s future is more complicated than ever before. He’s heading toward a payday and clearly has a love for Toronto and the Raptors organization, but something has to give and after a disastrous 2022-23 season, maybe it’s Siakam.

Further Reading

Scottie Barnes acknowledges DeMar DeRozan's daughter may have effected Raptors

Raptors season ends at free throw line as 2nd half collapse proves costly vs Bulls

Raptors talk Jakob Poeltl's impact & bench confidence as play-in vs. Bulls nears