How many championships would Raptors have won if Kawhi stayed?

As the 2010s progressed, the Toronto Raptors grew from an Eastern Conference bottom-dweller into a perennial playoff contender. Fast forward from their 2011 season where they won 22 games until 2018, and the Raptors held the best record in the East.

Even still, Toronto could not get over the hump. DeMar DeRozan and Kyle Lowry were a great duo, but there were not transcendent enough to get them past LeBron James and the Cleveland Cavaliers. So it made sense that in the summer of 2018, the Raptors decided to make a swing for the fences.

Putting together a trade package for a disgruntled Kawhi Leonard, Toronto acquired the superstar wing from San Antonio along with Danny Green, and their trajectory was instantly changed. They knew they had something special from day one, and that vision was realized in the form of a championship in 2019, the franchise's first and only.

After the Raptors reached the NBA mountaintop and the championship parade had drawn to a close, the question became: What's next? Would the organization be able to convince the ultra-skilled, incredible two-way playoff performer to remain in town?

Winning in 2019 likely gave Kawhi more reason to stay in Toronto

Everyone knew from day one that Kawhi's ultimate goal was to go play in Los Angeles. Hailing from Southern California, it was his dream to be able to go back home and play for either the Lakers or the Clippers while being close to family. And frankly, most people in his situation would desire the exact same situation.

But the prospect of winning a championship his first time around in Toronto seemed to have the potential to change things. Leonard wanting to go back home seemed natural before, but now? With the kind of team he had around him in Toronto?

It is understood that basketball is only one part of any person's life, even a top-level professional player. There are things just as important or more important than your career, and that is not typically something easily processed by the die-hard fan. But even so, Kawhi's dominant playoff run in 2019 had to have some kind of affect on his decision to leave or stay.

While he undoubtedly made a careful and well-planned decision, Leonard's choice to join the LA Clippers meant he left behind a potential dynasty in Toronto. It is hard to pinpoint precisely how successful that team would have been had he opted to remain a Raptor, but the overwhelming evidence says that they would have been a strong contender for many years to come.

The Raptors would have been a perennial contender with Kawhi

Employing the likes of Pascal Siakam, Serge Ibaka, Fred VanVleet, Norman Powell, OG Anunoby, Marc Gasol, Kyle Lowry and multiple high-level role players, the Raptors were a well-balanced team and were designed to win in the playoffs. There were certainly other talented teams in the East at the time, but Kawhi had already shown he could lead Toronto past talents like Joel Embiid and Giannis Antetokounmpo in the playoffs.

And as we saw, the East was still anyone's game at the time when it came to the postseason. The very next season, Giannis and the Bucks were on pace for 65+ wins before COVID hit, then they lost to the Miami Heat in the Conference Semifinals. If Leonard's Raptors had been there to take down the Heat, they would have ironically matched up with LeBron and the Lakers in the Finals in 2020, the matchup Kawhi was unable to obtain while playing with the Clippers that year.

While playing with the Clippers in 2019-20, Kawhi seemed to have his way with LeBron, Anthony Davis and company. It is not far-fetched to think Toronto could have gone back-to-back. From there, winning a third-straight obviously becomes near impossible, but the fact of the matter is that the Raptors would still have had the talent to compete for years to come in a system with an already-proven track record.

Again, numbers-wise, it is hard to say exactly how many titles this group would have won had they stayed together. But it certainly seems reasonable to think they would have had more success than the disappointing, injury-filled five-year run Kawhi has experienced in Los Angeles.