TORONTO — Over to you, Alex McKechnie.
Over to you, Darko Rajakovic.
Over to you, Scottie Barnes.
Over to you, Kawhi Leonard’s 35-year-old knees.
Bobby Webster got his part done.
Thanks to as big a swing as has been made on the Toronto sports scene since the last time they traded for Kawhi Leonard, the Raptors are a wholly different team heading into the 2026-27 season than they were just a week ago — or certainly since an injured and over-extended group came up short in Game 7 of their first-round series against the Cleveland Cavaliers.
After years of tiptoeing around landing one of the NBA’s big fish — a run for Kevin Durant here, a swing for Dame Lillard there — the Raptors have landed one of the league’s ultimate whales.
Again.
If all goes well, Leonard will — Toronto fans are hoping — be picking up where he left off when he departed the Raptors for the Los Angeles Clippers in free agency in the wee hours of July 2, 2019.
Almost seven years later to the day, the Raptors reached an agreement on the framework of a trade that will see 2025 all-star Brandon Ingram, 2023 first-round pick Gradey Dick and unprotected first-round picks in 2031 and 2033, a first-round pick swap in 2027, as well as second-round picks in 2030 and 2033 head to the Clippers for Leonard's services.
As well, it is expected that Leonard — who will earn $50.3 million this season — will get a two-year contract extension, which would likely be valued at about $126.1 million and would take the just-turned 35-year-old through his age-37 season.
It’s a bold move that seemingly came out of nowhere, only bubbling up into the NBA rumour mill in the past week. It’s a remarkable statement of intent by Raptors executive vice president and general manager Webster in his first solo run through the off-season since taking over as head of basketball operations in the wake of former team president Masai Ujiri’s departure last summer.
Webster received a five-year contract extension with the Raptors earlier this month and didn’t waste any time using the confidence the organization showed in him to make a high-risk, high-reward bet that has thrust the Raptors back into the heart of the NBA conversation in a way that hasn’t happened since before the pandemic.
The immediate term benefits could be tremendous, with Leonard adding his all-NBA play from last season to a group that finished fifth in the Eastern Conference, boasted the NBA’s fifth-best defence, and had the youngest overall roster in the playoffs.
The risk is that Leonard’s injury history catches up to him, robbing the Raptors of the short-term gains while mortgaging the club’s future, as they will be surrendering valuable draft assets when Leonard is long retired and Barnes is in his 30s.
But nothing ventured, nothing gained in the NBA, and standing pat carried its own risks. Ingram has two years and $81 million remaining on his contract, the second year a player option. One way or the other, the Raptors were going to have to make a decision on his future, neither of which they were likely thrilled about. If Ingram had a season comparable to what he put up last year, he was a sure bet to opt out of the final year of his contract, which would pressure the Raptors to either sign him to a long-term — and likely expensive — extension or begin exploring the trade market with uncertain returns given Ingram’s contract situation. Alternatively, they could let Ingram walk for no return at all. One way to think about the relative risk is that the Raptors chose the upside of a working relationship with Leonard for the next three years over tying themselves to Ingram or crossing their fingers on whatever his trade value would be in the coming 12 months. They chose Leonard.
The deal came together over the past 48 hours. Per sources, the two sides engaged in elevated discussions over the weekend but seemingly came to an impasse on Sunday as the Clippers were asking for more than the Raptors were willing to give: three first-round picks and some of the Raptors' top young players. The Raptors turned away requests for all-NBA rookie Collin Murray-Boyles and breakout second-year wing Ja’Kobe Walter. Even as negotiations picked up on Monday, one league source suggested that the Clippers were trying to extract second-year point guard Jamal Shead. No dice.
That the player compensation ended up being Ingram, the soon-to-be 29-year-old all-star, and Dick, who fell out of the Raptors rotation and was seeking a change of scenery in any case, explains why the pick compensation was relatively significant.
Still, that the Raptors landed the seven-time all-NBA selection and two-time defensive player of the year coming off one of the best seasons (a career-high 27.9 points per game with 6.4 rebounds, 3.6 assists and 1.9 steals on 50.5 per cent shooting, including 38.7 per cent from three) says plenty about Leonard’s determination to return to Toronto.
And why not?
His single year as a Raptor was almost scripted in terms of its dramatic arc, where Leonard went from a reluctant newcomer to pop-culture icon (“I’m a fun guy”; “Boardman gets paid”; Kawhine-and-dine), all while quieting doubters after a controversial (health-related) exit from San Antonio, where he had initially made his mark as one of the league’s two-way greats.
In a single, magical season, he led the franchise to its only championship, creating a dream sequence of highlights and memories: ‘The Shot’ that bounced on the rim four times before falling and eliminating the Philadelphia 76ers in Game 7 of the second round; his fast-break dunk over Giannis Antetokounmpo that nearly brought the (then) Air Canada Centre down as the Raptors pulled away from the Milwaukee Bucks in Game 6 of the Eastern Conference Finals; his “F-that, let’s get both” statement of intent before the Raptors swept the Golden State Warriors on the road in Game 3 and 4 of the Finals, paving their way to a title.
But nostalgia only goes so far in the NBA.
Part of Leonard’s calculation, undoubtedly, was that the Raptors were willing to pay him, and the Clippers were not. Once Los Angeles signalled that there wouldn’t be a contract extension coming, Leonard — as one source described it — began working to “strongarm his way out of there.” He identified an opportunity with the Raptors and did what NBA superstars do: he put his thumb on the scale and made it happen.
And now that he’s here, with the Raptors, the rest of the organization is on notice. Acquiring a player like Leonard at this stage of his career isn’t about building toward the future. However many healthy seasons that Leonard has left (one, two, maybe three?) is the timeline the Raptors are now operating under.
While it surely helped that the Raptors were willing to cut one more massive cheque, it certainly didn’t hurt that Toronto still employs Alex McKechnie as its vice president of player health and performance. The 74-year-old Scottish-born physiotherapist worked closely with Leonard in the 2018-19 season, returning him to his competitive peak after his injury-plagued exit from the Spurs.
But it will be a new test for Raptors head coach Darko Rajakovic, who will coach with real pressure to produce for the first time in his three seasons in Toronto. Rajakovic would sometimes explain poor performances last season by arguing the Raptors were “in Year 2 of a rebuild." That way of thinking will have to be retired, and Rajakovic — who is expected to get a contract extension shortly — will have to earn the respect of Leonard in short order.
It will also require Barnes to accelerate his development. As good as he was in his fifth season, deservedly earning second-team all-defence recognition, the level of play he delivered in the playoffs — he averaged 24.1 points, 6.1 rebounds, 8.6 assists, along with 1.1 steals and 1.7 blocks — will need to be more the norm than the exception if the Raptors are going to reach the heights expected after adding Leonard.
There is plenty of reason for optimism. In addition to one more payday, the Raptors offered Leonard a chance to join a team on the rise in an Eastern Conference lacking sure things beyond the defending-champion New York Knicks. Adding Leonard and subtracting Ingram — a talented scorer who led the Raptors with 21.5 points per game, but no one’s idea of a defensive stopper — should only further cement the Raptors' identity as a physical, ball-hawking group that makes life miserable for opponents.
There is a world where Leonard — still capable of locking down almost anyone, but more likely to pick his spots at this stage of his career and while carrying the offensive load he does — will be the second- or third-best defender on the floor when sharing it with Barnes and Murray-Boyles. It’s a scary thought for opponents and an exciting one for Raptors fans.
But the risk can’t be ignored.
When available, Leonard is undisputedly one of the NBA’s ultimate ceiling raisers, but injuries have plagued him throughout the prime of his career. His next season-ending injury could be his last.
He played just nine games in the 2017-18 season, the year before the Raptors traded for him in the first go-around. And while he was healthy enough in Toronto to play a carefully managed 60-game schedule and then lead the NBA in post-season minutes played, what was supposed to be a super team with the Clippers — being closer to his San Diego home and pairing with fellow two-way star Paul George was the reason he left for Los Angeles only a few days after the Raptors championship parade — was ultimately undone by Leonard’s creaky body.
He tore the ACL in his right knee in the playoffs in 2021, missing all of the 2021-22 season and 19 of 24 games to start the 2022-23 season. He then tore the meniscus in his right knee in the 2023 playoffs and was held out of most of the 2024 playoffs with inflammation in the same right knee, a problem that kept him off the American Olympic team that summer and sidelined him for the first 34 games of the 2024-25 season.
The good news? Since late January 2024, Leonard has played 103 out of a possible 127 games, playoffs included, and largely looked as dominant as ever.
If that’s the Leonard who returns to Toronto, the feeling around the Raptors won’t be nostalgic. Instead, it will feel familiar, with one of the greatest players to ever wear a Raptors uniform leading them back to heights not seen since he was last in it.
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