Russell Westbrook retirement sends heartbreaking reminder of Raptors' biggest what-if

Wednesday afternoon brought the surprising end of a legendary career for Russell Westbrook. The former MVP, Mr. Triple Double, and one of the most inspirational point guards of the 2010s called it a career after 18 years on his own terms.

As someone who has spent his entire life in Toronto and has always been a massive fan of Westbrook, his retirement couldn’t help but trigger a memory of arguably the biggest what-if in Raptors history.

For this, I take you back to the 2019 offseason, fresh off a championship; the Raptors were riding high until rumors started to swirl that their Finals MVP might not be re-signing. Kawhi Leonard hit free agency, fresh off a championship and seemed poised to return home to California with the Los Angeles Clippers. But he didn’t want to go alone because while being at home looked like his No. 1 priority, he still wanted to win and compete at the highest level.

This led to the Clippers' eventual pursuit of Paul George as they attempted to form an elite wing duo. But LA wasn’t the only team in pursuit of George, as the Raptors were right there, not only trying to acquire PG-13 but also Russell Westbrook.

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With the Thunder looking to enter a rebuild (one that ultimately led to a title in 2025), they were willing to trade both of their top players after a round-one loss to the Portland Trail Blazers. According to Adrian Wojnarowski, the Raptors were offering a package built around Pascal Siakam, fresh off a Most Improved Player season, and draft capital. From a financial standpoint, a deal for OKC’s tandem likely would’ve had to include a combination of Marc Gasol, Serge Ibaka and even Kyle Lowry.

But according to Wojnarowski at the time, Raptors president Masai Ujiri ‘balked’ at Sam Presti’s asking price for his two stars, ultimately leading to George being sent to LA for five first-round picks and Shai Gilgeous-Alexander. Toronto also wasn’t sure that trading for either player would’ve persuaded Leonard to stay. Woj also reported that, after things had gone through with the Clippers and Thunder, Presti was likely using the Raptors as leverage to net a giant return of five picks plus SGA from LA.

So while the Raptors may have only been used as a pawn in Presti’s plan to rob the Clippers blind, the idea that Toronto could’ve had a big three of Westbrook, George, and Leonard in 2019 is still unbelievable.

Just from a number standpoint, this duo would’ve been nearly unstoppable. Leonard had just averaged 26.6 points per game, made All-NBA and All-Defensive Second Teams, and Paul George just finished third in MVP and Defensive Player of the Year while averaging 28.0 points per game. And then there was Westbrook, still in his prime two seasons removed from winning MVP and coming off a 2018-19 campaign that saw him average 22.9 points, 11.1 rebounds, and 10.7 assists per game.

In an era of basketball still being dominated by big threes and front offices not prioritizing depth as much as they do in the modern NBA, Toronto would’ve potentially had the greatest big three ever. It may also have given Westbrook the one feather some felt was missing from his cap throughout his career: an NBA championship.

Enjoy retirement, Brodie—you deserve it!

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