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At this point, it’s almost a foregone conclusion: O.G. Anunoby is heading into free agency next summer.

Whatever hope the Toronto Raptors had that the organization would be able to work out an extension with the 25-year-old forward seemed to evaporate Friday night. It’s not Toronto’s fault, per se, but it’s the reality of the situation and the NBA’s new collective bargaining agreement isn’t going to help.

On the old C.B.A., the most Toronto could offer Anunoby in an extension was 120% of his salary or $100.2 million over four years. That wasn’t going to be nearly enough to get a deal done.

The new C.B.A. helped the Raptors a little, increasing the maximum to 140% of his salary or $116.9 million over four years. Prior to Friday night, an extension at least seemed plausible.

That was until Jerami Grant agreed to a five-year, $160 million deal with the Portland Trail Blazers and the possibility of an Anunoby deal evaporated. While Anunoby’s offensive numbers may not be quite as impressive as Grant’s, he’s younger, far better defensively, and the kind of player who can slide perfectly onto almost any roster.

Now Toronto finds itself in a difficult situation once again. Having just seen Fred VanVleet walk in free agency for nothing, the Raptors are faced with the reality that in a year’s time Anunoby can do the same.

Toronto will have options to keep Anunoby. The organization can still offer him more money and more term than anyone else: Five years, roughly $260.3 million is expected to be his max contract. But the Raptors also could have offered VanVleet a similar number but backed down when the prices became exorbitant.

If Anunoby isn’t deemed worthy of the max, Toronto’s leverage begins to disappear. While it’s tough to sit a year away from free agency 2024 and predict who will have cap space next summer, the VanVleet situation proved to always be ready for someone. To pick one example, the Indiana Pacers, who have long been connected to Anunoby, an alumnus of the Indiana Hoosiers, could create cap space next summer.

There is, of course, the other option, the one Toronto opted not to take with VanVleet, and move Anunoby. It wouldn’t be an easy pill to swallow for the Raptors who are already light on shooting, but it could be the prudent one.

Toronto has now watched as Kawhi Leonard, Danny Green, March Gasol, Serge Ibaka, and now VanVleet have all walked in free agency with no asset returns. It’s proved costly time and time again. The Raptors can’t afford to let it happen next summer for the sixth time in less than a decade.

Further Reading

Fred VanVleet Signs With Houston Rockets, per Report

Raptors Re-Sign Jakob Poeltl to 4-Year Deal, per Report

Report: Raptors Sign Dennis Schroder to Two-Year Deal