The Kawhi Question: Will he stay, or will he go?

Will Kawhi Leonard stay with the Raptors? The Raptors star appeared during the parade to be smiling while holding up one finger, perhaps agreeing to stay for one more year.

Standing on the top floor of a double decker bus, Kawhi Leonard laughed and smiled as the crowd lining the parade route chanted “one more year, one more year.” Then he held up one finger and smiled some more.

The crowd went wild.

As the dust settles on the 2018-2019 NBA season, the big question for the Raptors – and Leonard – is where the MVP will end up next season.

Leonard can explore free agency beginning June 30. Both he and Marc Gasol have player options on their contracts—Gasol for $25,595,700; Leonard for $21,329,750.

While it might make sense for 34-year-old Gasol to exercise that option and stay in Toronto for another year, Leonard is due a pay day and will get a maximum contract wherever he signs.

“MLSE has the financial heft to match any financial package, that's not going to be an issue,” said Rick Powers, a professor at the Rotman School of Management at the University of Toronto. “He'll be well-compensated wherever he goes.”

Powers said whatever pitch the Toronto Raptors make to Kawhi Leonard will include the sponsorship and endorsement opportunities that exist here in Canada.

“He is a winner and that’s what advertisers look for. That’s what sponsors look for,” Powers said. “So, they will flock to him.”

But money isn’t everything when it comes to the introverted superstar. He left the San Antonio Spurs because he was unhappy there, despite being one year away from a maximum deal. Toronto can offer him more money than the L.A. Clippers, but he has made his desire to play in his native Los Angeles clear in the past.

“It's really comfort level and just a place where he can win,” said TSN 1050 host Matthew Cauz.

Despite lacking a bonafide superstar, the Clippers were able to push the Golden State Warriors to six games in the first round of the 2019 playoffs. If they’re able to sign Leonard, the Clippers would still have the cap space to bring in another superstar and make a run for the franchise’s first-ever NBA title.

But in Toronto, there is a genuine opportunity for a repeat if the Raptors can keep this team together.

Of the starters, Gasol, Leonard and Danny Green are all free agents come the end of the month; Kyle Lowry and Pascal Siakam are both signed through to 2020.

There’s also the question surrounding the future of Masai Ujiri, the man who built this championship team. Rumours are swirling that the Washington Wizards want to offer him big money and an equity stake in the organization, but Powers isn’t convinced Ujiri will leave the team he has built.

“He needs to run this through the course,” Powers said. “And that will be trying be trying to win one, two, three more championships. After that, why wouldn't he look at another opportunity?”