Who on this core could contribute to a future Raptors championship?

The Raptors are about to face a financial crunch. What can they do to avoid being destroyed?

Over the course of this entire season, the Toronto Raptors have become less than the sum of their parts. There is inarguable talent, particularly at the top end of the roster. Why do so many teams want what the Raptors have within the top five or six? Mostly because everyone in that position is an exceptionally talented player. For a variety of reasons, they simply have failed to coalesce together this season. That has manifested in extraordinary dominant games — such as against the Sacramento Kings or Portland Trail Blazers in recent weeks — sandwiching a failure against the Golden State Warriors that saw simple back cuts slice Toronto’s defense to shreds.

The Raptors still have eyes on a championship. But perhaps realistic projections no longer predict 2023-24 as the start of the title window and are now are looking a little later down the line. And unless you’re playing NBA 2k, teams won’t and can’t do entire overhauls over the course of a few seasons and be competitive. If the Raptors do contend for a championship two-to-four seasons down the road, at least some members of the current roster will be there, fighting the good fight.

Who? Doing what? Let’s dive in to answer those questions, peeking behind the veil at what competitiveness might look like in the medium-term future.

This is the boring stuff, but let’s start with the financials to look at how outside factors can impact the changing shape of Toronto’s roster. Organized here by rotation players (who I’m considering as at least possible to remain on the team after next season) whose contracts are expiring soonest:

After 2022-23

Fred VanVleet (if he declines his player option)

Gary Trent jr. (if he declines his player option)

Thad Young (if the Raptors decline to guarantee his contract for next season)

After 2023-24

Pascal Siakam

O.G. Anunoby (if he declines his player option)

Precious Achiuwa (will be a restricted free agent, so Raptors are almost guaranteed to retain him)

After 2024-25

Chris Boucher

Scottie Barnes (will be a restricted free agent, so Raptors are almost guaranteed to retain him)

Christian Koloko (will be a restricted free agent, so Raptors are almost guaranteed to retain him)

It is likely that no matter what happens, Koloko will remain with the team. He’s an extraordinary defensive prospect who probably doesn’t have immense trade value around the league, so barring a shocking trade, Koloko will be around. Similarly, the Raptors have a long future of team control over the employment statuses of the Chaos Cousins, and fortunately for the Raptors they work unbelievably together. So that’s three players who will be around, making up quite a strong frontcourt: Barnes, Achiuwa, and Koloko. Looking three years down the road, I imagine Barnes will likely be a top-30 (ish) contributor at minimum around the league and a surefire star, while Achiuwa certainly has his own paths to reach that status. That’s a good base of certainty.

But who else on today’s roster will be around? There are some fairly obvious breadcrumbs the Raptors’ front office has left us in regards to their team-building philosophies that are important to review. One: the Raptors aren’t going to spend into the luxury tax unless they believe they have a championship-contending roster. Two: if the Raptors re-sign the current team in its entirety, including Trent and VanVleet, Toronto will be in the luxury tax. Three: based on Toronto’s 23-28 record, the Raptors are not a championship contender at the moment, nor will they be without some fairly drastic external help. (In other words, it’s unreasonable to expect development for players currently on the roster on its own to boost this team into the championship conversation).

So add all that together, and not everyone on the roster today is going to be here within a season or two. Smoke from reports by connected insiders seems to indicate that Trent is the most likely player to be moved. (Our own Samson Folk dug into the pros and cons of that exact possibility here). But Trent is a talented scorer and excellent shooter — those players aren’t exactly impossible to find in today’s NBA. Context helps Trent a huge amount in his current role, but ultimately the Raptors are a fair amount better with him on the bench. Given his positive trade value at the moment, Toronto’s looming tax bill, and the fact that of everyone among Toronto’s top-end players, he’s the most easily replaced, I imagine it’s quite likely Trent will be traded. In a vacuum, he helps this team a lot, and he’s in the midst of the best season of his career. This is not a critique of Trent. Just recognition of unfortunate realities that have been exacerbated by Toronto’s losing.

On top of that, expect the Raptors to decline to guarantee Young’s salary for next season. (That’s not reported info, but it would make sense given his on-court contributions this year.) If those are the only cost-cutting moves, and let’s pretend that the Raptors trade Trent for expiring money and a pick, the Raptors could re-sign VanVleet to his desired salary, draft players, and still be below the luxury threshold for next season. They would not be operating as a below-salary cap team, so it’s not like Toronto could make significant free-agency additions. And losing Trent just to save money? The Raptors would be further from championship aspirations, not closer.

Oh yeah, and then when Toronto would have to re-sign Anunoby, Siakam, and Achiuwa (he’s gonna get a real large raise) the following offseason, it would be in the luxury tax anyway. So even trading Trent for ostensibly nothing (not that that would happen, but just to make my financial point) would only kick the luxury-tax bill down the road a season.

That means the Raptors are likely to deal more than just Trent this trade deadline. VanVleet is playing like a bonafide star again, and he should have positive value this deadline if the Raptors deal him. (If he goes to a contending team that asks less of him, and is able to support him with more and more dynamic guards in the rotation, that team will see its title chances boom. I see a VanVleet deal as potentially the key to this year’s championship, much like Marc Gasol in 2018-19.) (Again, Samson discussed the pros and cons of a VanVleet deal here.) Anunoby has been dangled on the trade market for some time, and the Raptors are making it seem like three first round picks aren’t enough to steal him away from Toronto. Siakam, if the Raptors opt for a total rebuild, would be the most valuable player of all.

There are two distinct possibilities. One, the Raptors avoid the luxury tax by tearing down the team — it would take more than a Trent deal to accomplish this. Two, the Raptors improve the team via trade to the extent that paying the luxury tax is amenable because they are championship contenders.

In regards to the first, the Raptors would probably have to sell the farm. The original remaining trio of Barnes, Achiuwa, and Koloko would be the only safe names, and the Raptors would push the contention window far down the road, perhaps six or eight years. I doubt outside of those three, any of Toronto’s current players would be likely to be on the roster at that point. The Raptors would acquire a king’s ransom if they tore down the whole roster this deadline, and it would take a huge amount of time for those picks to eventually become productive players competing for a championship. A whole lot could happen between now and then, including the whims of ping-pong balls, so it’s basically impossible to predict.

In regards to being a buyer at this deadline and becoming a championship contender in the short term, I discussed a few possibilities here and here for possible trade targets who could improve the Raptors to that extent. My explanations for both players are much longer in those pieces, but even though both are risks, I see Zach LaVine and Karl-Anthony Towns as the two mostly likely such possible acquisitions. Toronto would need to keep Siakam, or else there wouldn’t be enough talent to contend anyway. But it would need to trade a whole heck of a lot of talent to acquire one of those players. Most likely, Anunoby and some other valuable players would go out the door. Perhaps Trent? And, woah, the picks the Raptors would need to offer. The Raptors could also trade VanVleet, but given his impending free agency, age, injury status, and productivity, there’s virtually no way they could trade him and become better in the short term. If they’re trying to become a championship contender for next season, VanVleet would have to stay.

Is that a championship team? Say, the starting lineup of VanVleet-LaVine-Barnes-Siakam-Achiuwa? Or VanVleet-Barnes-Siakam-Achiuwa-Towns? How about the middle ground of VanVleet-Buddy Hield-Barnes-Siakam-Myles Turner with Achiuwa and Trent coming off the bench?

Hard to say. The Raptors would need to rebuild a whole lot of depth. One underrated component of that 2019 championship squad was the depth; Toronto was better in the regular season with Kawhi Leonard resting games, and it was so deep that Anunoby missed the playoffs and it didn’t matter. This year’s Raptors are nothing like that. Maybe Boucher remains a contributor, and Koloko would become a really impressive bench big within a season or two, but the Raptors would need much more for the above potential starting groups to contend. There’d need to be bench wings, dynamic bench guards, shooting, and more. Sub-.500 teams usually don’t trade their way into championship contention, so you’d have to think the Raptors aren’t a normal sub-.500 team (which very well might be true).

But every step along that road is treading length-wise on a thin, risky blade. Building a championship contender on the fly is hard, and even though the Raptors have plenty of talent, there’s a big gap between talent and contention. It would be possible, but it would be very risky, considering the Raptors could end up becoming a middling playoff seed, never contending for championships, and simply ending up where they are now a few seasons down the road but without picks.

There is a middle ground. Toronto could deal some of its big-name contributors at the deadline but not all, keeping the contention window firmly in the two-to-four year range. Maybe Trent, VanVleet, and Anunoby are sent packing, with heartfelt thank-you videos upon their returns, but Siakam stays. That would push the luxury tax far down the road. Of course, Siakam would have to okay such a situation and want to re-sign when his contract is up, so there’s risk in that option, too. But maybe the Raptors could try to have their cake and eat it too. Then the foursome of Siakam, Barnes, Achiuwa, and Koloko become the four who’d stay and start over together again. That’s a whole lot of talent that is proven to fit together, and the Raptors get another chance to building a team that works around that core. Trading Trent, VanVleet, and Anuonby would give the front office a hoard of players and picks from which to choose in building that roster.

No matter what, there’s so much risk for Toronto. In the big picture, the team has an extraordinary outlook. The team has all its future first-round picks. The young talent in Barnes and Achiuwa is almost unmatched leaguewide. The veteran talent is established. But because they haven’t put it all together, now this trade deadline represents the cliff edge that eventually Toronto must tumble down. At least they get to choose how they fall. Unfortunately, choices must be made because of finances — without the luxury tax, none of these problems would exist. And the lesson of this season, given all that’s happened, is this: Losing can foul even the most pristine of waters. Now it will be up to the front office to unsnarl the vines and turn the Raptors’ long-term outlook back into an oasis before the well is poisoned.