"Kawhi Leonard just felt all along, it was going to take the full year to sell him on Toronto. It wasn't going to be done in training camp or by Christmas or by the trade deadline. But I do think they've made progress with him. I do think they've made pretty good progress with him from the sense I have. They put themselves in it. And when Kawhi showed up there, I'm not sure he imagined any future in Toronto. I do think it's a serious consideration now."
Kawhi is a Riverside, California, native who has been linked heavily to the Los Angeles Clippers and Lakers, but considering Toronto's success this season as the No. 2 seed in the Eastern Conference, re-signing may represent his best chance to win a championship in the coming years.
Wojnarowski pointed to Leonard's relationship with point guard Kyle Lowry and the development of forward Pascal Siakam as possible factors that could help convince the star to remain in Toronto.
Above all else, though, Wojnarowski believes the Raptors' biggest selling point is their ability to be a perennial contender in the Eastern Conference, along with the fact that they can pay Leonard more than any other team:
"I think the Kawhi thing is getting really interesting there. For them to just get through this series and get to a Conference Final, every day is the case you're making. And, oh by the way, 'We can pay you more than anybody else. If you want to be in L.A. and you want to live there in the offseason, there's only so many days you really have to be in Toronto in the snow. You can get out of here. You're on the road half the time. The rest of the year, you can get out of here and go in L.A. and be in California.'
"But Toronto is selling winning on him. They can't sell geography to him, I don't think. I don't think they can't sell weather on him. There's nothing they can do about that. When you have that kind of organization, you sell winning and again, the chance to make the most money."
Toronto acquired Leonard in an offseason trade with the San Antonio Spurs with the knowledge that he could leave after one season. Even so, it was a worthwhile risk since the Raptors struggled to make noise in the playoffs during the past several campaigns despite their regular-season success.
With Leonard in the fold, the Raptors are tied 2-2 with the Philadelphia 76ers in their second-round playoff series.
Kawhi has been the biggest reason for their playoff success. After averaging 26.6 points, 7.3 rebounds, 3.3 assists and 1.8 steals during the regular season, Leonard is putting up 32.3 points, 7.7 rebounds, 3.4 assists and 1.0 steal per game during the postseason.
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Leonard won an NBA Finals MVP award with the Spurs, and if he and the Raptors can get past the 76ers, his presence gives them a chance to go all the way.
Dating back to January, the belief around the NBA has reportedly been that Leonard would either re-sign with the Raptors or leave for the Clippers in free agency, per ESPN.com's Tim Bontemps.
The Clippers pushed the Golden State Warriors to six games in the first round of the playoffs despite the lack of a true superstar, so it could be of great interest to Leonard to sign close to home with the Clips and lead a talented core that includes Lou Williams, Danilo Gallinari and Montrezl Harrell.
Although the Clippers have been mentioned more often as a landing spot for Leonard than the Lakers, the allure of playing alongside LeBron James must be considered as well.
If winning is Kawhi's biggest priority regarding his free-agent decision, then beating the Sixers and advancing to the Eastern Conference Finals could be the deciding factor in retaining one of the NBA's top players.