Kawhi Leonard
(Photo by Christian Petersen/Getty Images)

In a stunning and unthinkable narrative, the Toronto Raptors amazingly made the Kawhi Leonard acquisition a win-win.

In what is one of the coldest deals in recent memory, Gregg Popovich and the San Antonio Spurs shipped off two-time All-NBA First-Team star Kawhi Leonard along with Danny Green to the Toronto Raptors for DeMar DeRozan, Jakob Poeltl and a protected 2019 first-round pick. Knowing that the former California Mr. Basketball has his sights on Los Angeles, the Spurs did not cater to his desires and shipped him off for what they deemed to be the best package available.

While most see trading for Kawhi as a gamble, he is exactly the opposite. He could push Toronto past Boston and Philadelphia this year, while also being the perfect rebuilding chip in a trade or the big expiring contract that sets up a modern era team for an ideal rebuild. He sets them up for the future, no matter the outcome.

In a deal that a lot of the media has declared as a victory for the Spurs because of Kawhi’s unwillingness to stick around, the Raptors still have put themselves in the exact spot that they want. Kawhi makes them an instant contender to make the NBA Finals and they dump the player that was never able to take them there.

Although it seemed all of Canada was upset about moving DeMar DeRozan, it is something that the front office had to do. He has been an awful postseason performer. He has disappeared in playoff games over the course of his career, contributing greatly Toronto’s postseason struggles. Moving off of his contract might have been exactly what they wanted to do, especially given the results from recent years.


The Raptors were swept in this year’s conference semifinals, marking the third straight year that the Raptors were knocked out by the Cavaliers and the second straight year they were swept. They have won just two of 14 games against Cleveland in the playoffs during the past three years.

During that stretch, DeMar DeRozan often went rogue. In fact, when former Raptors head coach Dwayne Casey benched DeRozan in Game 3, the team nearly came back and won. It was time for a reset in Toronto.

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Let’s look at the present:

For starters, Kawhi is a massive upgrade over DeMar DeRozan. He is a far better defender who has won at the highest level. If he can get back to form, he is one of the three best players in basketball. The team around Leonard is set up for him to win as well.

The Raptors have a fantastic young core. Fred VanVleet, 24, is a talented point guard who looked better than Kyle Lowry at some points last season. One of the shockers about the Kawhi trade was that it didn’t include OG Anunoby, one of the best young players Toronto has to offer. His 7-foot-2 wingspan had some comparing him to Kawhi Leonard coming out of college. He has the potential to be a lockdown defender at multiple positions. The 21-year-old along with Leonard will give Toronto one of the best defensive looks in basketball. Pascal Siakam, 24, also put together a good year, increasing his minutes and playing crucial time in the postseason.

This young team, along with Kyle Lowry, Jonas Valanciunas and Danny Green should make them one of the best teams in a weak East. If Leonard plays up to his potential in a contract year, they might be the team to beat. If the team succeeds and makes it to the NBA Finals, maybe they could convince Leonard to stay. Paul George had LA on his radar as well, before settling in Oklahoma City. Toronto is a fantastic basketball city with some of the best fans in the league. With their young core, very little committed salary in the near future and a weak conference, it’s a compelling argument to hear out.

Who says he will even finish the season in Toronto?

The option to deal Kawhi before the end of the season is still on the table. Instead of simply letting him walk, the Raptors could flip him before the trade deadline if he pulls more shenanigans. They could send him to either LA team and get a sweet return. Maybe they could pry Brandon Ingram from the Lakers if they think Kawhi could help them get over the hump and they cannot wait for free agency.

The Raptors supposedly had their eye on Shai Gilgeous-Alexander from Kentucky before he was snagged by the Clippers in this year’s draft. A package involving him and Tobias Harris would give the team another offer to consider.

If this all blows up and he leaves, the Raptors still have options.

Their young core gives them something to build on. One of the underlying parts of the deal is that DeRozan’s contract is now off the books, making it so they will only have one guaranteed contract (along with rookie deals) in 2020. They have $73 million coming off the cap from just Lowry, Valanciunas and Serge Ibaka in upcoming years. This will give them incredible flexibility, which is perfect in the new era of player movement in the league. Toronto will be in an ideal rebuilding situation, with all their draft picks and a ton of cap space.

Knowing they might have hit their ceiling with DeMar DeRozan, the Raptors are getting a guy in Kawhi Leonard that they aren’t certain will stick around. However, they seem to be set up for the future either way. They might be able to convince one of the best players in the game that playing in a weaker conference will lead to more success and an easier path (see LeBron James’s game plan for the past eight years). They could still trade him and get something in return before he leaves. If it all goes bad, they will be loaded with cap space soon and all their draft picks.

So, the next time you hear about Toronto taking this gamble, stop and think about if they really did that. It isn’t a gamble if there isn’t a bad outcome.

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