What's the best path for the Raptors next season?

The future may start now, but there's still time to do it better

If Masai Ujiri could give a spiel about winning at every practice, post game presser, and every day in between, he probably would.

His latest public appearance, first in conversation with Matt Devlin regarding the extensions for Scottie Barnes and Immanuel Quickley and then taking questions from the media, featured that mantra that “We will win in Toronto.”

The point of amusement came at the very end of his session with the media, when his patended dialogue was followed up by a simple question of “When?”

Ujiri has been stressing patience since last season’s trade deadline and that nervous laugh followed by “We’ll see” screamed — at least in my opinion — that this is going to be an extended process.

Granted, there’s no way to answer that with certainty. No one anticipated that Kyle Lowry and DeMar DeRozan would lead the franchise to the level of success they did in 2013-14 and by the very next season they were already victims of their own success after a 49-win season worthy of the fourth seed ended in a first-round sweep at the hands of the Washington Wizards.

Therein lies the tricky part of this latest rebuild effort. I mentioned in the previous post that 2024-25 will be the last season with low expectations for Scottie Barnes and Immanuel Quickley. Cover your ears, Raptors fans, I think the organization needs to take advantage of those low expectations and be bad now to be better when real expectations kick in.

Barnes will earn $10.1M this upcoming season before his salary balloons to $38.7M the following season. Quickley will be earning a flat $32.5M in 2024-25 and that number will remain the same for the following four years of his contract (He can earn up to $12.5M more over the five years based on meeting incentives). R.J. Barrett’s services will cost $25.8M in the upcoming season and just under $58M over the course of the next two seasons.

Bruce Brown Jr. will cost the team $23M next season after his team option was picked up. With Gary Trent Jr. out of the picture, it’s unfortunate the Raptors couldn’t renounce Brown, find an agreement with a suitable free agent (or two) and delay the Quickley re-signing until they did so (because of Quickley’s low cap hold).

If Toronto could have acquired a first-round pick for Brown, it would have happened by now. As of this moment, it will be about hoping he can be a better version of himself for the Raptors at the start of the season and contending teams feeling a greater urge to acquire him.

All told, the Raptors currently have about $170M in guaranteed salaries to pay next season, the luxury tax limit is about $171M, the first apron at $178M, and the second apron at $189M. With this inflexibility, I do believe it makes another poor season record-wise the most viable option for 2024-25.

Now, that doesn’t mean you have to come out of the gate with one mission in mind. The Raptors were 17-17 at one point in the Tampa season before going into a 10-28 tailspin to land the seventh best odds which led to the fourth pick and Barnes. Even this past season, the team was 15-21 before finishing 10-36 the rest of the way and landing the eighth pick that went to San Antonio. You can compete for about half the season before recognizing that pushing for a ninth or 10th seed isn’t really worth it.

Barnes may not like it, as he suggested when he rebuffed claims that the Raptors are even in a rebuild:

I absolutely love that answer. It’s the attitude you want the franchise player to have and the competitive spirit that should keep the front office on their toes. He also has about 45 million reasons to be as competitive as possible and maximize his chance of making an All-NBA team next season.

Having said that, the reality of the East — barring injury — is this: Boston, Philadelphia, New York, Milwaukee, Orlando, Indiana, Cleveland, and Miami all project to be better next season. That’s the top eight seeds in some shape or form out of the picture. Toronto certainly has a case to be better than the rest, but is the ninth or 10th seed really the optimal outcome for the franchise when you know you have your own pick in a very good draft after sending this year’s to San Antonio?

Emphasizing winning habits with a new core is certainly an important part of good culture building and holding all involved accountable. As someone who’s generally been anti-tanking, I’m not going to say it’s wrong to compete. When you lose relevance, it’s a long road back.

I also feel that the second apron brings along a tectonic plate shifting set of rules that forces your hand and so the thinking needs to adapt accordingly. With the Raptors likely to be at best mediocre next season, right up against the luxury tax, and having messed up the Siakam trade, maximizing the quality of next year’s pick feels essential to increasing the odds of top tier success.

Denver is a prime example of just how punitive the second apron can be. Despite having a three-time MVP, having won a championship a year ago, and having their core of Nikola Jokic, Jamal Murray, and Michael Porter Jr. secured long-term, they ceded Kentavious Caldwell-Pope to Orlando because of potential second apron implications after already suffering a key loss in Bruce Brown last off-season. Who’s being prioritized? Their own picks in Christian Braun, Peyton Watson, and Julian Strawther.

The idea of a dynasty is already fading with six different champions over the last six years and the second apron is set to make the concept extinct. Boston looked a class above this season but with new ownership on the way and their two star players on long-term deals worth in excess of $300M, hard decisions are just around the corner. Tiny championship windows will become the norm and hence the increased pressure for front offices to become little things kings.

Do I think finishing with the ninth or 10th seed is a bad path? No. I just don’t think it’s the optimal path and nailing those margins is crucial right now. At this point, it’s hard to predict just how bad you need to be for a legitimate shot at a top-four pick.

In the 2022-23 season leading up to the Victor Wembanyama draft, it was almost as if the NBA sent out a memo about avoiding tanking from the very beginning and so there were just four sub-30 win teams (Detroit, San Antonio, Houston, Charlotte). Last season, with a relatively weaker draft, there were seven sub-30 win teams (Detroit, Washington, Charlotte, Portland, San Antonio, Toronto, Memphis).

This year, you expect Detroit, Brooklyn, Washington, and Portland to definitely be worse than Toronto. Atlanta and Utah are also in play depending on what happens with Trae Young and Lauri Markkanen, respectively. Being in that mix for the sixth to eighth best lottery odds should be in play. As noted earlier, you don’t have to be dreadful from the very beginning to be in the mix for lottery odds outside the top four.

Is there a real path to a sub-30 win season? Possibly, especially considering the lack of certainty at the shooting guard position and the genuine opportunity to prioritize development.

The backend of last season was such a drag because players like Jordan Nwora with no real future with the franchise were getting minutes and any of the players with long-term outlooks were either injured or away from the team for personal reasons. This season, you could actually have the likes of Ja’Kobe Walter, Jonathan Mogbo, Jamal Shead, and of course Gradey Dick making real strides at the end of the season. Even big minutes for Davion Mitchell could be worthwhile.

After all the struggles of last season and the constant debate about whether conveying the pick to San Antonio or not would be worth it, I get it’s hard to fathom the idea of another bad season.

The past is the past, though, and just as there was a poster titled ‘The Future Starts Now’ to introduce Barnes and Quickley’s new extensions, it won’t really start until the following year and navigating this upcoming season the right way is a decision that the organization needs to get right.