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There was so much angst surrounding the Toronto Raptors’ first Kawhi Leonard trade.

A lot of it had to do with giving up DeMar DeRozan, a good-if-flawed player who had shown unyielding loyalty to the Raptors and seemed to truly enjoy being the face of the franchise. Beyond that, there was wild speculation that Leonard might not report to Toronto, and certainly concerns that even if he showed up, his heart wouldn’t be in it. It seemed to ignore that the Raptors were only giving up DeRozan, Jakob Poeltl and a 2019 first-round pick for Leonard, and that LeBron James had just departed for Los Angeles, leaving the Eastern Conference wide open.

Masai Ujiri, Bobby Webster and the front office were taking a calculated risk with a roster that had smashed its head on the ceiling multiple times. Eight years later, Webster, now running the Raptors with Ujiri in Dallas, has taken a much bigger risk. With their trade for Leonard, the Raptors could wind up being on a downswing just as they are about to be without two of their own picks in the span of three years. Leonard will be out of the league, while the end of Scottie Barnes’ prime will probably be in sight. That is a scary downside following a trade for an injury-prone 35-year-old player.

However, there is a huge upside, and it’s one Raptors fans already know: Even at this age, Leonard has been one of the league’s best 10 players whenever he’s on the floor. He is significantly better than Brandon Ingram on a per-minute basis, and now the Raptors don’t have to spend more time hoping Ingram will become a player he is not. Primarily, Webster is betting on three things: the Raptors’ medical staff, the strength of the culture and style that coach Darko Rajaković has built and, above the rest, Scottie Barnes.

While this is an aggressive, win-now trade, it leaves the Raptors some flexibility to make future moves. Leonard, clearly, is more valuable than Ingram and Gradey Dick. The risk, then, lies in the draft picks they are surrendering — a first-round pick swap in 2027 and unprotected first-rounders in 2031 and 2033. The Raptors are also moving two second-rounders.

It’s frightening to be without those picks so far off into the future, but structuring the deal like that allows the Raptors to further prune the roster. They can still trade the other end of the 2027 swap as well as their 2029 pick. They can also move swaps in 2028, 2030 and 2032. If Poeltl, again a Raptor if you haven’t been paying attention, holds up as poorly as he did last year, they might have to, given he is owed $56.8 million in 2027-28 and 2028-29, the same two years Leonard’s extension is likely to cover.

If the trade was a bit richer in picks than expected, it should be noted that the Raptors managed to keep all three of Collin Murray-Boyles, Ja’Kobe Walter and Jamal Shead, their most important players on rookie contracts. They also kept Allen Graves, whom the Raptors picked with the 19th selection of last month’s draft.

The Raptors will need those young players to perform because it will be hard to add to the roster. Leonard is entitled to a 15 percent trade kicker, which the Clippers would pay but would go on the Raptors’ cap sheet. (Players can also waive a kicker, as Marc Gasol did in 2019 when the Grizzlies traded him to the Raptors.) That could raise Leonard’s 2026-27 salary from $50.3 million to $57.5 million, and immediately put the Raptors over the luxury-tax threshold with just 12 players signed to main-roster deals. Alijah Martin, a 2025 second-round pick who spent last year on a two-way contract, became the 12th player after he signed a two-year deal worth $4.8 million on Wednesday, according to a team source, who was granted anonymity because no deals are official during the league’s moratorium. The second year of the deal is a team option. A team must carry at least 14 players on standard NBA deals.

According to a team source, the matter of Leonard’s trade kicker is still undetermined, with the Raptors considering several different structures to allow them to fill out their roster. A lot should be clearer by Monday at noon, when the moratorium is lifted.

However, because the Raptors used the salaries of Ingram and Dick to bring back more salary than they traded away in the form of Leonard, the Raptors are “hard-capped” at the first apron, which is set at a smidge beyond $209 million, this season. As of now, Leonard isn’t in a position to accept his trade kicker because Immanuel Quickley, RJ Barrett and Poeltl have $6.5 million worth of incentives that count toward the hard cap, even if they are not ultimately reached, per The Athletic’s John Hollinger. If you don’t understand that, just realize that there is more maneuvering to come. The issue has to be resolved, one way or another.

The luxury tax shouldn’t be a worry. The whole point of having Leonard is that you’re trying to win at a high level immediately, and that’s when you’re supposed to spend. Whether or not Leonard gets his trade kicker, the Raptors are unlikely to be able to offer more than minimum contracts to fill out the roster.

(As such, this might give last year’s second-round pick, Alijah Martin, who is currently a restricted free agent, and this year’s second-round pick, Jaden Bradley, a better shot of getting spots on the main roster. The minimum salaries for first- and second-year players count for less against the cap than minimums for any other level of experience, which slot in as if they are attached to second-year players for cap purposes. Still, the Raptors should probably be looking for a veteran centre as Poeltl insurance.)

Matters could get really complicated for the two years after that. Let’s assume Leonard gets a maximum-value extension, which would be based on the cap in 2027-28. For now, it seems as if it would be around two years and $126.9 million, with a starting salary in 2027-28 close to $62 million. That would have the Raptors with nearly $184 million in commitments for seven players — not including Barrett or Shead. The Raptors have full Bird rights on Barrett and will have the same on Shead if he finishes the season with the Raptors, so they can pay either whatever they want. However, that would bring the punitive aprons into play. The ownership group Maple Leaf Sports and Entertainment, led by executive chair Edward Rogers, and the Raptors will have some decisions to make.

A few things are non-negotiable. Vice-president of player health and performance Alex McKechnie, who had an excellent rapport with Leonard, will need to keep him largely healthy. Leonard said he was in a good place following the Clippers’ season, and that his surgically repaired knee hasn’t been a problem recently. Leonard played 68 games in 2023-24 and 65 in 2025-26. If he can play anywhere close to that — and as importantly, be able to make it through the playoffs, which was frequently a problem in Los Angeles — the Raptors should be delighted.

The more I think about it, though, the more this trade is a vote of confidence in Barnes. He had a very good season last year, but scored more than 20 points in just five of his 26 games after the All-Star break. The playoffs showed a different version of Barnes. He was still a defensive terror and a playmaking weapon, but he also averaged 24.1 points on 60.5 percent true shooting, which factors in the added importance of 3s and free-throw attempts. It was just a seven-game sample, but the Raptors likely wouldn’t have made this trade if Barnes didn’t show he was capable of that kind of play.

Expecting him to replicate what he did in seven games over a six-month season is silly, but the Raptors will need Barnes to be closer to that version of himself if they are to have a successful regular season. Remember, led by Kyle Lowry and Pascal Siakam, the Raptors went 17-5 in games Leonard did not play in during the 2018-19 season, helping them get the second seed in the Eastern Conference. Considering they escaped the second round by the slimmest of margins, winning Game 7 on their home court at the buzzer, that seems relevant. Excuse the most Toronto comparison ever, but who is Barnes, at his best, if not a mash-up of Lowry and Siakam?

That is why the Raptors can dream of this trade working out. Leonard is a much simpler fit than Ingram, and infinitely more proven in the playoffs. His shooting alone is crucial for the Raptors. While he has dominated the ball frequently since he left San Antonio, he knows what it means to play “0.5 basketball” based on his time with the Spurs. The Raptors finding a middle ground between throwing it to Kawhi and an egalitarian offense based on player and ball movement seems attainable.

He is not the world-wrecking defender that he was in his prime, but Leonard is still a nasty one-on-one deterrent. Imagine a lineup of Shead, Walter, Leonard, Barnes and Murray-Boyles, for example. The Raptors finished fifth in points allowed per possession last year. Health-willing, they should be able to repeat, if not improve on that.

The Raptors have opened themselves up to a lot of risk here. Also, the East is more competitive than it was in 2018. The New York Knicks have earned favourite status, while the Boston Celtics, Miami Heat, Detroit Pistons, Indiana Pacers, Cleveland Cavaliers and Philadelphia 76ers can all shoot for more than 50 wins, and they should not be called pie-in-the-sky dreamers for it. The offseason is far from done.

Now the Raptors can include themselves in that group. There are no guarantees, but this could be delicious theatre. And that’s why we watch sports.