And with Leonard on an expiring contract, head coach Nick Nurse is well aware of the pressure on the franchise to make the enigmatic swingman feel at home.
So much so, in fact, that he admitted to being a little on edge before the two met for the first time.
"There's a certain sense of, I don't know if nervousness is the right word, but a little bit of uneasiness," Nurse told The Athletic's Eric Koreen. "You want to make a good first impression. It's obviously a big move for the organization. You want it to go well. Knowing he was not known as a guy who said much ... of anything at all, I considered what would happen if he didn't really say anything. What was I gonna do?"
As it turns out, Nurse's nerves never got the best of him.
"Before getting into his routine, Nurse asked Leonard if he had any questions; the star had a few, and what Nurse feared would be a speech turned out to be more of a conversation," Koreen wrote. "According to the coach, that spirit has carried over to telephone discussions, as well as to on-court meetings in Leonard’s home base of San Diego suburb La Jolla as well as Los Angeles."
Once training camp begins later this month, the Raptors will have an exclusive nine-month period to prove why Leonard should re-sign with them next summer—just as the Oklahoma City Thunder did with Paul George a year ago.
And while Leonard has yet to indicate what his intentions are, Danny Green—who was also acquired by Toronto in July—recently said he believes Toronto could wind up winning him over.
"I don't know where his mind is at for the future. I can't predict or tell you. I can just tell you that the city of Toronto is gonna be hard to turn down after being there," Green said on his Inside the Green Room podcast, (h/t The Score's Wael Saghir). "I've been going every summer for the past 10-plus years. It's a great city, and the fans are amazing."
If Leonard does leave, it's widely believed he will head back to his hometown of Los Angeles. According to ESPN.com's Adrian Wojnarowski and Chris Haynes, Leonard had "been clear that he plans to sign with the Los Angeles Lakers in free agency next summer" prior to his trade to the Raptors.