Kyle Lowry and Kawhi Leonard
Kyle Lowry and Kawhi Leonard helped the Toronto Raptors win the 2019 NBA Finals. In this picture, Lowry and Leonard of the Raptors look on during the first half against the Boston Celtics at TD Garden on in Boston, Massachusetts, November 16, 2018. Tim Bradbury/Getty Images

In the three-team race for Kawhi Leonard, the Toronto Raptors might have the most at stake. Re-signing the 2019 NBA Finals MVP would allow the champions to defend their crown. Failing to keep the superstar could end up forcing the team to completely shake up a roster that just delivered the franchise its first-ever title.

Toronto traded DeMar DeRozan for Leonard last summer, knowing that a rebuild might be on the way. The Raptors had reached their ceiling with DeRozan and Kyle Lowry as the centerpieces of the team, suffering a string of playoff disappointments, unable to get over the hump—and past LeBron James—to win the East.

It didn’t matter that Leonard was a year away from free agency and had made it clear he wanted to be in Los Angeles. The Raptors were never going to win a championship unless something changed.

Raptors’ president Masai Ujiri fired 2018 Coach of the Year Dwane Casey and pushed all of his chips into the middle of the table, ready to break up the team in the seemingly likely scenario that Leonard would walk in 12 months.

The Raptors gambled and won. Toronto ended the Golden State Warriors’ dynasty with Leonard looking like the best player in basketball. It will go down as one of the greatest trades in NBA history.

Leonard is still considering playing in L.A. The superstar might end up going to the Los Angeles Lakers or Los Angeles Clippers, forcing Toronto to revisit their plans from a year ago.

ESPN’s Adrian Wojnarowski said on Friday’s edition of “The Woj Pod” that the Raptors would have “absolutely torn the team down” if they didn’t trade for Leonard. If Leonard says goodbye to Toronto, the Raptors will no longer be a title contender, the team mostly made up of players on one-year contracts.

Toronto could try to see how far they can get with Pascal Siakam as their top player. Currently a year away from becoming a restricted free agent, Siakam emerged as the Raptors’ second-leading scorer with All-Star potential this past season. Toronto even went 17-5 during the regular season when Leonard didn’t play, indicating they could reach the 2020 playoffs without him.

For the long-term health of the organization, the Raptors might be better off exploring the trade market for veterans that can sign elsewhere for the 2020-2021 season.

According to ESPN’s Brian Windhorst, Marc Gasol is among the players that league executives believe could be traded in the near-term if Leonard leaves Toronto.

Gasol, 34, was a key acquisition for the Raptors at February’s trade deadline. He’s also past his prime and recently picked up a player option for $25.59 million next season.

Trading for Gasol made sense when Toronto was pursuing a championship. Sending him to another team that hopes to make a title run would also be a logical decision for the Raptors.

Kyle Lowry finds himself in a similar position. He’ll turn 34 years old and make more than $33 million next season before hitting free agency in the summer. The point guard could be a valuable addition for another team that has its eyes on making the 2020 NBA Finals.

It wouldn’t be shocking to see Lowry be sent elsewhere, even after helping deliver a championship to Toronto in his seventh season with the team. The Raptors were willing to deal the face of the franchise a year earlier. Lowry even found himself at the center of trade rumors in February when Toronto was one of the best teams in the league.

Lowry’s 14.2 points per game in 2018-2019 were his fewest in six years. He averaged a career-high 8.7 assists per game.

It’s a safe bet that Serge Ibaka would become available in the event that Leonard leaves Toronto. He’ll make more than $23 million in the final year of his contract.

Danny Green is still a free agent. Unless Leonard returns to Toronto, he’s expected to sign with the Lakers or Dallas Mavericks.

Leonard can make this easy for the Raptors. Choosing to stay north of the border would keep Toronto’s roster almost entirely intact, making them the favorites in the East.

If Leonard doesn’t stay, the Raptors will have to answer some of the same uncomfortable questions they faced before Leonard’s arrival.