As we tip off the 2026-27 season, I don’t begrudge NBA fans who are desperately trying to make sense of this past offseason. We are right there with you. LeBron James and Jaylen Brown are Sixers? Giannis Antetokounmpo is in South Beach? The Washington Wizards gave Trae Young how much?
The biggest plot twist, however, involves our friends north of the border. In the aftermath of the stiffest punishment in NBA history handed down by commissioner Adam Silver on LA Clippers owner Steve Ballmer and his eternally beleaguered franchise, Kawhi Leonard has largely escaped unscathed. And not only that, Leonard, the grand prize of the Clippers’ cap circumvention, has returned to the team that originally flagged cap circumvention shadiness to the league office when he left — the Toronto Raptors.
Yes, Kawhi Leonard is a Raptor, picking up where he left off in 2019 in a quest to bring another title to Canada. He continues what is the most confusing NBA legacy of his generation. A two-time Finals MVP, seven-time All-NBA selection and two-time Defensive Player of the Year who, as of now, is no lock to have his jersey retired by any of his former teams.
It’s a question that I can’t stop thinking about as NBA fans wrestle with how one of the game’s greats will be remembered following a historic cap scandal: Do the Raptors represent Leonard’s best shot at having his jersey retired?
In the player empowerment era, the fascinating case of Leonard could help shape the legacies of his superstar peers who jump from team to team.
Leonard’s legacy?
Imagine telling an NBA fan in 2017 how this Kawhi Leonard story would play out. At the time, Leonard had earned back-to-back Defensive Player of the Year awards, had already won a championship and a Finals MVP. The Spurs were coming off back-to-back 60-win seasons and Leonard was the face of it all.
If you look up in the rafters at the Spurs’ arena, you’ll see Timmy, Tony and Manu’s jerseys up there. And for a while, it seemed like Leonard’s No. 2 jersey would be right next to them.
But things in San Antonio soured quickly. After some disagreements about how the team handled his knee injury, Kawhi’s magical rise with the Spurs had a sudden and bitter downfall. Leonard played just nine games in the 2017-18 season and, in the summer of 2018, the Spurs traded Kawhi and Danny Green to the Raptors for DeMar DeRozan, Jakob Poeltl and a top-20 protected 2019 first-round draft pick.
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Spurs fans weren’t happy with how it all went down. Every time Leonard played in San Antonio, boos rained down from every corner of the arena. But Gregg Popovich, Leonard’s longtime coach, was not pleased with it. In a November matchup in 2023 against Leonard’s Clippers, Popovich took the PA announcer’s microphone in the middle of Leonard’s trip to the free-throw line and demanded an end to the booing.
"Excuse me for a second," Popovich said. "Can we stop all the booing and let these guys play? Have a little class. That's not who we are. Knock off the booing."
Coach Pop’s backing was unusual, but it did reveal a continued heartfelt connection with his former Finals MVP who left on uneasy terms. Leonard’s reception in San Antonio may still be icy, but if history is a guide, the team will honor him one day with a jersey retirement.
And so will the Raptors. Even if he played just one season in Toronto.
The case to retire Kawhi’s jersey
In January, the Raptors will hold a ceremony to retire Kyle Lowry’s No. 7 jersey alongside Vince Carter’s No. 15 in the Toronto rafters.
Lowry’s case is a no-brainer. He appeared in 409 Raptors wins, making him the winningest player in franchise history. He is also the franchise leader in assists, steals, made 3s, triple-doubles and All-Star appearances. And for that, just a few weeks ago, the Raptors unveiled their Kyle Lowry statue, which is comically not Lowry at all, but a dinosaur with a basketball jersey on.
Though it may seem controversial now, it seems likely that Kawhi Leonard’s No. 2 jersey will join No. 7 and No. 15 one day.
Based on one standard, there’s no question that Leonard will have his jersey retired by the Raptors.
I researched every Finals MVP winner in NBA history and looked to see if the franchise had retired their jersey. And here are the facts: There have been 28 Finals MVPs who are no longer playing in the NBA. All 28 of them have seen their jerseys rise up to the rafters of their respective buildings.
That list of Finals MVPs includes Cedric Maxwell of the Boston Celtics and Andre Iguodala of the Golden State Warriors. They are the only Finals MVPs who have had their jersey retired but not been inducted into the Hall of Fame. And they help set a precedent for Leonard, who won Finals MVP in both San Antonio and Toronto.
But here’s the thing: Maxwell and Iguodala each logged eight seasons with their Finals MVP teams. If it weren’t for this trade back to Toronto, Leonard would be the shortest-tenured Finals MVP in league history. A one-and-done mercenary of this magnitude had never been seen before. Besides Kawhi, no player had ever left his team immediately after winning the Finals MVP. (That is, if you exclude Michael Jordan’s two retirements with the Bulls.)
According to my research — which, I should note, excludes memorial jersey retirements like Reggie Lewis in Boston and Bobby Phills in Charlotte — Leonard would become one of four honored players who played fewer than four seasons with the team. Another caveat, this list does not count those who were players and coaches for their club, like Lenny Wilkens and Nate McMillan in Seattle, who muddy up the picture.
SHORTEST NO. OF SEASONS JERSEY RETIRED
Player | Franchise | Tenure (Yrs) |
Michael Jordan | MIA | 0 |
Kawhi Leonard* | TOR | 1 |
Nate Thurmond | CLE | 2 |
Julius Erving | BKN | 3 |
Jordan had his No. 23 retired by the Miami Heat in 2003 when legendary coach and exec Pat Riley decided to pay tribute to MJ. It is the one instance of an NBA team retiring a jersey of a player who’s played less than a season with their club. (Did you ever wonder why LeBron James wore No. 6 and not No. 23 in Miami?) Nate Thurmond had his No. 42 jersey retired by the Cleveland Cavaliers despite playing in just one and a half seasons with the team and averaging a measly five points per game as the backup center. Look up “The Miracle at Richfield” sometime and you’ll begin to understand Thurmond’s legacy in Northeast Ohio. Not to mention the future Hall of Famer was from Akron, Ohio.
Kawhi is under contract for three more seasons thanks to a contract extension signed this offseason. He can opt out after two seasons, which would bring his total seasons in Toronto to three. Even if Kawhi plays just three seasons in Toronto, it wouldn’t be the shortest tenure.
Julius Erving had his jersey retired by the 76ers, but also by the Nets. In just three seasons with New York, Dr. J led the Nets to two championships and won three MVPs in the ABA.
Let’s say Kawhi picks up his player option for the 2028-29 and finishes out his career with the Raptors after four seasons. How exclusive is the Four Seasons club? There are nine players who have had their jerseys retired with just four seasons in uniform. Shaq has done it twice.
The underlying throughline for most of these guys is relevant to Kawhi — seven of the 10 instances were driven by a championship run.
JERSEY RETIRED WITH JUST 4 SEASONS
Player | Franchise | Tenure (Yrs) | Titles |
Clyde Drexler | HOU | 4 | 1 |
Shaquille O’Neal | MIA | 4 | 1 |
Oscar Robertson | MIL | 4 | 1 |
Wilt Chamberlain | PHI | 4 | 1 |
Bill Walton | POR | 4 | 1 |
Dave Twardzik | POR | 4 | 1 |
Lionel Hollins | POR | 4 | 1 |
Pete Maravich | ATL | 4 | 0 |
Charles Barkley | PHX | 4 | 0 |
Shaquille O’Neal | ORL | 4 | 0 |
Given that every retired Finals MVP has had his jersey honored by his team and the fact that there have been several instances of retired jerseys for players with short tenures with their club, Kawhi can expect to see No. 2 join No. 7 and No. 15 one day in Toronto.
NBA superstars will be watching how the Raptors handle Leonard’s situation.
What about other NBA superstars?
In the player empowerment era headlined by LeBron James, it’s common for the modern NBA superstar to switch teams in their prime, leaving their various franchises with some tough decisions about jersey immortality.
Kevin Durant, for example, will have a fascinating case ahead of him. Will the No. 35 be retired in OKC? One hint is that, a year after KD left, PJ Dozier was allowed to wear No. 35 for OKC in 2017-18.
"Honestly I didn't even think twice about [Durant having it] ... I just saw it was open and took advantage of it."
The Thunder could still decide to honor Durant one day, and I suspect they will. His jersey could be retired by the Golden State Warriors as well, even though he played only three seasons there. He won two titles (and two Finals MVPs) in the Bay like Dr. J in New York. Elsewhere, Brooklyn, Phoenix and Houston would have less pressure to do so considering he didn’t reach past the second round in any of those three stops. Yet.
In the non-Finals-MVP department, Anthony Davis should also be curious about Kawhi. Davis left New Orleans on icy terms and, like Kawhi, won a title in his first season with his new club, the Lakers. Davis played longer in LA than Kawhi did in Toronto, but the Lakers may be a little pickier considering they have so many numbers retired as is.
Jimmy Butler is another superstar with a chance of retiring without being honored by a team. The six-time All-Star and five-time All-NBA standout has made a lasting impact in Chicago and Miami, but enough to be honored with a jersey retirement?
Chris Paul has strong cases in New Orleans and Los Angeles, but the latter franchise has seemingly sent the wrong messages. The Clippers already gave Paul’s No. 3 to Bradley Beal this summer, months after they waived Paul unceremoniously in the middle of his farewell tour. It seems ludicrous that LA wouldn’t honor Lob City with jersey retirements for Paul, Blake Griffin and DeAndre Jordan. But according to Griffin, he isn’t exactly holding his breath on having his jersey retired by the Clippers.
But the guy who might be watching Kawhi’s legacy closest? How about Paul George?
When they joined forces in 2019, it marked the biggest free agency coup in franchise history and both seemed destined to be honored by the Clippers one day. Now, after the Kawhi scandal has tarnished his tenure with the team and considering George’s association with that era, it’s not looking too good that either of them will have their jerseys retired in the Intuit Dome.
Which leads us to this unbelievable fact. The Clippers are the only NBA team to not have any retired numbers in their 57-year history. Not from their San Diego days or the Buffalo Braves days. Zero jerseys hang in the Intuit rafters. Every retired Finals MVP has had his jersey raised to the rafters by his respective team, but not every MVP, as it turns out. The Clippers, who came from San Diego after the Buffalo Braves relocated, have not retired Bob McAdoo’s jersey despite him winning the MVP award in 1975 with the Braves. It’s a shame the Clippers should correct soon.
That’s maybe the most twisted thing about this entire Kawhi Leonard jersey retirement story. He was the Clippers’ best chance at having their first jersey up in the rafters. But now? Good luck getting that past Adam Silver.
The Clippers keep circumventing their own chances at having a jersey retirement ceremony one day. But as Leonard kicks off his second tenure with Toronto, he's all but certain to have his jersey retired by the Raptors. A second championship would remove all doubt.