Wednesday afternoon brought a stunning end to Russell Westbrook’s run, with the former MVP and “Mr. Triple Double” stepping away after 18 years on his own terms.
Sometimes you don’t realize you’ve already seen the finish line until it’s gone.
You had to be there. And now it’s over. pic.twitter.com/6YoOW8WyIV
- Russell Westbrook (@russwest44) August 12, 2026
For anyone in Toronto who grew up watching Westbrook, that retirement note does more than close a legendary career. It drags up one of the biggest what-ifs in Raptors history.
Go back to the 2019 offseason. Toronto had just won a championship, but the mood shifted fast when it became clear Kawhi Leonard might not come back.
Leonard hit free agency after the title, with the Los Angeles Clippers looking like his destination as he neared a return home to California. Even then, he wanted more than a homecoming.
He wanted to stay in a place where he could still chase wins at the highest level.
That set the Clippers on the path to Paul George, as they tried to build an elite wing pairing. But the Raptors were in that chase too, and they weren’t only trying to land George. They were also in the mix for Westbrook.
With Oklahoma City preparing to rebuild after a first-round loss to the Portland Trail Blazers - a rebuild that eventually led to a title in 2025 - the Thunder were open to moving both of their top players. Adrian Wojnarowski reported at the time that Toronto’s offer was built around Pascal Siakam, fresh off a Most Improved Player season, plus draft capital. Any deal for the full Oklahoma City package would also have required Toronto to juggle salary, with Marc Gasol, Serge Ibaka and even Kyle Lowry part of the financial equation.
Still, Wojnarowski said Raptors president Masai Ujiri “balked” at Sam Presti’s asking price for the two stars. That hesitation helped push George to Los Angeles, where he was sent to the Clippers for five first-round picks and Shai Gilgeous-Alexander. Toronto, meanwhile, also wasn’t convinced that bringing in George or Westbrook would have been enough to keep Leonard in the fold.
Woj also reported that once the Clippers and Thunder finalized their deal, Presti may have been using Toronto as leverage to drive up the Clippers’ return.
That leaves the Raptors with a tantalizing picture that never became real: Leonard, George and Westbrook all in Toronto in 2019.
On paper, it would have been ridiculous. Leonard had just put up 26.6 points per game and earned All-NBA and All-Defensive Second Team honors.
George had finished third in MVP voting and Defensive Player of the Year voting while averaging 28.0 points per game. Westbrook was still in his prime, two seasons removed from his MVP award, and coming off 2018-19 averages of 22.9 points, 11.1 rebounds and 10.7 assists.
In a league still ruled by big threes and less obsessed with depth than today’s NBA, that group might have been the most terrifying one imaginable. And for Westbrook, it could have delivered the one thing that never made it into his trophy case: an NBA championship.
In Other News...
Raptors Suddenly Have A Real Shot At A Veteran Wing Fit
The Raptors search for another sturdy wing defender just got a little more interesting. Phoenix waived Haywood Highsmith, opening the door for a player who has bounced through a few stops but has built a reputation as a tough, role-friendly piece on the perimeter. For a Toronto roster that has spent plenty of time looking for wings who can defend, move without the ball and fit into a larger rotation, that kind of profile is at least worth a long look.
Highsmiths path has been a winding one, and the health piece only adds another layer to the evaluation. He is coming off meniscus surgery and played only seven games for the Suns last season, so any team considering him has to balance the fit against the uncertainty. Still, for a club like Toronto, the appeal is obvious enough to keep the conversation alive as the market settles. [Read more 🡒]
Raptors Could Have A Stunning Kawhi Path Without The Full Price
The Raptors pursuit of Kawhi Leonard has taken a strange turn, one that leaves Toronto waiting on the NBAs next move before the deal can officially go forward. The original agreement sent Leonard to the Clippers as part of a package that included Brandon Ingram, Gradey Dick, two unprotected first-round picks, two second-round picks and a pick swap, but the trade is now on hold while the league reviews allegations tied to how Leonards contract was put together.
If the investigation ends with a finding of cap-circumvention wrongdoing, the entire picture could change for Toronto in a way few teams ever get to imagine. Instead of paying the full trade price, the Raptors could suddenly be positioned to chase Leonard in free agency, while commissioner Adam Silver has said the league hopes to wrap up the matter by the end of the summer. [Read more 🡒]
Raptors May Have One Kawhi Problem They Cant Fix Midseason
The Raptors path forward after the Kawhi Leonard trade is starting to look less like a clean upgrade and more like a cap-sheet puzzle they may have to live with all season. Toronto has built a roster with real top-end money tied up in key pieces, which gives the team some quality but little room to maneuver if it wants to sharpen the bench or find another rotation-level player before the deadline.
Jamal Shead and JaKobe Walter are among the salaries that could be moved if Toronto tried to create flexibility, but that kind of deal would come with its own awkward tradeoff. For a team trying to stay in the mix while Leonard remains part of the picture, the bigger issue is whether the front office can improve the roster without sacrificing the kind of depth it is trying to build in the first place. [Read more 🡒]