The Los Angeles Clippers are trading Kawhi Leonard back to the Toronto Raptors, according to ESPN. The deal sends Leonard to the team with whom he won the 2019 championship and Finals MVP. That summer, he left Toronto to sign a free-agent deal with the Clippers. Now, seven years later, the Raptors are bringing the most talented player in franchise history back to Canada in one of the biggest trades of the offseason.
The return package for the Clippers includes Brandon Ingram, Gradey Dick, unprotected first-round picks in 2031 and 2033, a pick swap in 2027 and two second-rounders (2030 and 2033), per ESPN.
The Leonard era in Los Angeles included some of the highest highs in franchise history, but ultimately ended in disappointment. After trading Shai Gilgeous-Alexander and a historic package of draft picks to the Oklahoma City Thunder for Paul George in order to secure Leonard’s commitment, the Clippers only reached one Western Conference Finals with Leonard on the team. That was the first conference finals appearance in team history, but Leonard missed that series after tearing his ACL in the prior round against the Utah Jazz.
Meanwhile, the NBA is investigating whether the Clippers circumvented the salary cap through a sponsorship agreement between Leonard and Aspiration to direct more money to Leonard. That investigation has been ongoing since last offseason. The Clippers have maintained their innocence since the allegations, brought to light by reporter Pablo Torre, came to light.
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After years of injuries, Leonard has bounced back over the past two seasons to return to All-NBA form. Yet as the Clippers traded James Harden and Ivica Zubac at the deadline to launch a youth movement, a Leonard deal eventually seemed inevitable. However, with Leonard on an expiring contract, he had control over his possible destinations. After all, the whole league saw him leave Toronto the first time despite winning a championship. In fact, Leonard was reportedly only interested in signing an extension with his two former teams: the Raptors and the San Antonio Spurs.
Toronto has rebuilt its team entirely since Leonard last played there. No players from the 2019 championship team remain on the roster, and both top executive Masai Ujiri and coach Nick Nurse are gone as well. But current Raptors general manager Bobby Webster was part of the front office that built those 2019 champions, and last year, he put together a roster that had a surprisingly successful season.
The Raptors won 46 games, earning the No. 5 seed in the Eastern Conference behind a breakout season from Scottie Barnes, who made his second All-Star appearance. Despite playing the first round of the playoffs with several significant injuries, the Raptors managed to push the Cleveland Cavaliers to seven games in a near-upset. With Barnes ascending to true stardom, the Raptors decided to push to get back into genuine Eastern Conference contention. So let’s grade this trade for both sides:
Toronto Raptors: C+
Toronto adds star to pair with Scottie Barnes — but at a significant risk and cost
When the Raptors traded for Ingram at the 2025 trade deadline, they seemingly did so knowing that Scottie Barnes is an incredible all-around player whose biggest shortcoming would be clutch scoring. Ingram was supposed to be their late-game shot maker, and for most of last season, he was.
But he was overmatched in the playoffs before he got hurt. Even without him and Immanuel Quickley, Barnes thrived. He pushed the Cavaliers to seven games in the first round while functioning as the point guard. That series showed Toronto that Barnes is ready for a higher level of contention. He just needed the right co-star.
The Raptors wanted a half-court shot maker. Leonard is an apex half-court shot maker. There will be a bit of positional overlap since Barnes last season started taking more of the mid-range shots that Leonard prefers. But that’s a solvable problem considering how well Leonard can shoot from deep. Leonard needed to play with a younger star who could keep him fresh across the 82-game grind. Barnes needed to play with an end-of-game killer who could carry his team across the finish line in the closing minutes. In that respect, they both got exactly what they needed. The Raptors generated the fourth-most fast-break points in the NBA last season. If they maintain their turnover generation and willingness to run while adding Leonard’s half-court brilliance, their offense has a chance to be very, very good.
Leonard is not the same level of 48-minute defender that he was when he won Defensive Player of the Year, or even when he was last a Raptor. But, again, he won’t need to be. Toronto has great defenders everywhere. The trio of Barnes, Leonard and Collin Murray-Boyles is among the best defensive frontcourts any team can put on the floor this season. Jamal Shead is tiny, but a ferocious point-of-attack defender. Ja’Kobe Walter falls between Shead and the big wings: not quite imposing enough for the strongest forwards and centers, but a headache for most guards he encounters.
Toronto should be among the very best defenses in the NBA. The Raptors ranked fifth last season, and that was with Ingram in Leonard’s place and Murray-Boyles still finding his footing as a rookie. Now they are not only loaded with talent, but also with versatility. They genuinely have enough wing defense and size to switch every screen if they want.
You could make a compelling case that the Raptors are now the Eastern Conference’s second-best team. The Boston Celtics are in a state of flux with Jaylen Brown on the trade block. In the Eastern Conference Finals, the Cavaliers got absolutely waxed by the New York Knicks — as did almost everyone else. We’ll see how Tyrese Haliburton looks as he returns to the Indiana Pacers following his torn Achilles. The Miami Heat are trying to build around Giannis Antetokounmpo with minimal resources. The Detroit Pistons are still looking for a secondary scorer.
On paper, the Raptors probably have the most balanced roster of any of them. They pose a far more severe threat to New York than anyone in the East did last year… if they can stay healthy.
Raptors taking major risk at hefty price
The immediate questions here are medical. Toronto, led by the highly regarded vice president of player health and performance, Alex McKechnie, did an excellent job of keeping Leonard healthy during the 2018-19 season. He’s much older now, and the Raptors just made a significant investment in him moving forward. Leonard is eligible for a contract extension, and reports have indicated that Toronto was the only team he was willing to sign with. A big extension could go poorly, given Leonard’s age and history of injuries. It’s hard to imagine the NBA allowing this trade to go through if the results of its investigation into Aspiration could affect Leonard’s status with the Raptors, but it is worth noting that the investigation is still technically ongoing in the background here. We don’t know what its findings could mean for Leonard.
Now we have to address the compensation. In a vacuum, two first-round picks and a swap are a reasonable price for someone as accomplished as Leonard. What matters here is which first-round picks Toronto gave up: a 2027 first-round swap that’s non-trivial considering the swap rights the Clippers owe to the Thunder… and unprotected picks in 2031 and 2033.
In the NBA right now, there are effectively two classes of first-round picks. There are picks covered by lottery reform that come between 2027 and 2029, and then there are picks slated to convey after that. In the simplest terms, we do not know what the lottery rules will be in 2030 and beyond. The lottery reform the NBA recently adopted lasts only through 2029. The rules could change in ways that could be enormously advantageous for these picks. Miami is the only other team to trade multiple picks in the 2030s this offseason, but did so for a 31-year-old Antetokounmpo.
Leonard is four years older and has a more extensive injury history. It is at the very least improbable that he remains in Toronto when these unprotected picks eventually convey, and if he’s still there, he’ll be a different player. Now, Barnes, 24, and Murray-Boyles, 21, are young. If they’re still in place, the Raptors should remain competitive. But the NBA is a cruel and random league, and no team can just assume it’s going to be great five and seven years down the line.
Perhaps more importantly, giving up these picks now costs Toronto the liquidity it might need to build a team around Barnes and Murray-Boyles later. Even if Leonard is great for a few years, who is going to be the scoring star the Raptors pursue when he ages out of his own stardom? Lacking those 2030s picks will make it harder for Toronto to find that player if it needs to.
Had these picks been in the 2020s, I would have given the Raptors a “B” or a “B+.” They made their team significantly better and potentially entered the championship picture by making this deal. You don’t compete for championships without taking some risks. There’s one trophy at the end of the season and 29 teams don’t win it. The Knicks just won theirs, in part, by giving up far more to get a far worse player in Mikal Bridges. Whether it was Leonard or someone else, the Raptors were going to take this risk on someone.
But given all the risk factors associated with Leonard, whether or not Toronto should have pulled the trigger here is probably a toss-up. It doesn’t have the sort of downside risk that, say, the Phoenix Suns took on when they traded all of their picks for Kevin Durant. But there’s no such thing as guaranteed success with trades. The risk here was enormous… but the reward potentially could be as well.
Even if the Raptors aren’t quite at the level that, say, the Thunder or the Spurs are, they weren’t at the level the Golden State Warriors were in 2019 either. All it takes is one injury, one lucky break, and if you put yourself in a position to take advantage, you can break through and win a title. I think the Raptors are there now. They once again have a puncher’s chance at the trophy that only Leonard has ever been able to get them.
Los Angeles Clippers: A+
Clippers execute brilliant pivot, ship out Leonard at peak of his value
A move like this became inevitable the moment the Clippers traded for Harden, and perhaps as far back as their initial acquisition of Leonard. The Clippers thankfully just completed their obligation to the Thunder from the Paul George trade… but now still owe three years’ worth of pick control to Oklahoma City and the Philadelphia 76ers for the Harden acquisition. They have been operating at a substantial asset disadvantage for years now. As Leonard aged, it became clear that the championship window he once opened was closed.
From a medical standpoint, Leonard is something of a time bomb. He appeared in just 266 of a possible 472 games in his first six seasons with the Clippers. Had Los Angeles tried to move him after last season, the value return likely would have been minimal. But Leonard just played 65 games at an All-NBA level. Considering he just turned 35, the odds of him remaining that available next season and beyond are not great. Leonard’s trade value was never going to be higher than it was this offseason, and with no championship upside in keeping him, the Clippers had little choice but to act. Since the Raptors were the only team Leonard was known to be willing to extend with, the Clippers didn’t have much leverage to drum up any sort of bidding war.
Under that context, getting the specific picks they got is frankly astounding. This is a potential franchise-altering move for the Clippers, who are suddenly in a pretty enviable long-term position. Let’s start with that 2027 swap. Before this trade, the Clippers were essentially guaranteed to pick at the bottom of the first round. Not only do the Thunder have the right to swap with them, but Oklahoma City can force them to take Denver’s pick instead of their own. Now, the Clippers buy into some Toronto downside risk in case Leonard gets hurt, and the Thunder can’t access this pick.
Why 2031, 2033 unprotected picks are so valuable
The picks in the 2030s are the potential game-changers here. They are among the most valuable outstanding draft assets in the NBA, and the job the Clippers have done in pivoting off of a doomed era over the past six months has been an outright front office masterclass. In January, they had a near-the-end Harden, a near-the-end Leonard and an in-his-prime Zubac who quietly was not playing quite as well as he had in his breakout 2024-25 campaign.
They turned those three players into an All-Star point guard a decade younger than their old one in Darius Garland, Bennedict Mathurin, who they could still re-sign in restricted free agency, the No. 5 overall pick in this year’s NBA Draft (Keaton Wagler), three valuable future first-round picks (2029 from Indiana and 2031 and 2033 from Toronto) and that quietly interesting 2027 swap. This should be the blueprint for how middle-of-the-standings front offices with older rosters try to pivot. Once they wait out the pick control they still owe from the original Harden trade a few years back, they’ll be among the more asset-rich teams in the NBA.
So what is the plan with this newfound flexibility? I would imagine it’s something like the one they put in place after Chris Paul left in 2018 to join the Houston Rockets. The Clippers re-signed Blake Griffin that offseason only to flip him for more assets. They preserved cap flexibility moving forward — as they are positioned to do now — with the idea that at some point in the near future, there would be another disgruntled star or two who wanted to come play in Los Angeles. That’s ultimately what happened, and they secured Leonard and George.
In the interim, the idea will be to develop their young players and remain competitive enough to attract future stars. That’s a pretty attainable goal. Ingram is flawed and disappointed for Toronto in the playoffs, but he also made the Eastern Conference All-Star Team last year at the NBA’s scarcest position. He can at least slide into Leonard’s small forward slot and give the Clippers some offense. Dick was a former lottery pick. It never quite clicked in Toronto, but maybe the Clippers can get him back on track. The Clippers have the flexibility to add talent this offseason. Garland was terrific after his arrival from Cleveland. The Clippers managed to win 48 games without Paul or Griffin in 2019.
This is a very competent organization with a great coaching staff. They are not going to be pushovers if Garland can just stay on the court.
It’s going to take the Clippers a few years to re-enter the championship picture, but if they do so, it will be because of the trades they’ve made over the past six months. They turned one of the bleakest outlooks in the entire NBA into a near blank canvas with plenty of youth and future draft capital to work with.
The Leonard era may not have been as successful as they hoped, but they can now move forward with the hope of one day building something better.
