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Raptors right to swing for fences with Kawhi Leonard

San Antonio Spurs v Phoenix Suns

PHOENIX, AZ - DECEMBER 15: Kawhi Leonard #2 of the San Antonio Spurs on the bench during the second half of the NBA game against the Phoenix Suns at Talking Stick Resort Arena on December 15, 2016 in Phoenix, Arizona. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Christian Petersen/Getty Images)

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NBCSports.com’s Dan Feldman is grading every team’s offseason based on where the team stands now relative to its position entering the offseason. A ‘C’ means a team is in similar standing, with notches up or down from there.

The Raptors are one step closer.

To seriously contending for a championship? To actually rebuilding?

We’ll see.

But Toronto is racing toward a resolution, one way or another.

Last offseason, the Raptors positioned themselves for a breaking point in the summer of 2020. They gave Kyle Lowry and Serge Ibaka three-year contracts, matching the timeline of Jonas Valanciunas’ contract ending. The hitch was DeMar DeRozan’s huge deal, which ran through 2021. If it reached the point Toronto president Masai Ujiri wanted to retool in 2020, perhaps DeRozan wouldn’t be as appealing on the trade market. Keeping DeRozan – central to the Raptors’ identity – could have been even more limiting.

So, Ujiri got ahead of that potential problem by trading DeRozan, Jakob Poeltl and a top-20-protected first-round pick for Kawhi Leonard and Danny Green.

The move was extremely risky. Leonard missed nearly all of last season due to injury. He can become an unrestricted free agent next summer, and he’s reportedly eying Los Angeles.

But Leonard is just 27 and only one season removed from being an MVP candidate. He could lift Toronto to a championship this season. He could re-sign. The upside is so high.

The downside is starting a rebuild that probably would have come anyway.

First, the Raptors will give it their best shot this season.

They re-signed Fred VanVleet – the driving force behind their excellent bench – to a two years, $18 million contract. That likely assures paying the luxury tax for the first time since 2004, though there’s still time to shed salary before the tax is assessed on the final day of the regular season.

Greg Monroe was a very nice addition at the minimum. If all goes well, he might even allow Toronto to dump Valanciunas’ salary.

And don’t forget about Green, who’s a solid contributor on the wing, not just a throw-in with Leonard.

Firing Dwane Casey to hire first-time NBA head coach Nick Nurse was another risk. I wonder whether Ujiri would have done it if he knew he’d acquire Leonard later in the summer.

The Raptors could be excellent this season and beyond. They could be excellent this season then fall off dramatically. They could be far worse this season and stay down a while.

But after years of strong regular seasons and playoff disappointments, it was time to change the status quo.

Fortune favors the bold.

Offseason grade: A