Webster told Dan Woike of the Los Angeles Times on Thursday that the Raptors expect some correlation between the length of their postseason run and Leonard's desire to stay, but they don't believe it's the only factor.
"Of course there is [a link between postseason success and Leonard's potential desire to re-sign]. There is," he said. "... It's not all about what happens at the end of the season. It's about what's gone on to this point. From the day we acquired him, it's the ground work."
The comments come one day after ESPN's Brian Windhorst reported on The Jump that there's widespread belief around the league the two-time Defensive Player of the Year will leave the Raptors this summer.
"A lot of people in the NBA think Kawhi is out of [Toronto]," Windhorst said. "It's not because of anything the Raptors did. Kawhi kind of wants to be on the West Coast. The difficulty is that he doesn't really articulate his feelings to people."
Toronto acquired Leonard as part of a blockbuster trade with the San Antonio Spurs in July alongside Danny Green for DeMar DeRozan, Jakob Poeltl, a 2019 first-round pick and cash. Questions were immediately raised about whether the deal amounted to a one-year rental since the 2014 NBA Finals MVP has a player option in his contract for next season.
The 27-year-old Los Angeles native has remained mostly quiet about his future throughout his first, and potentially only, campaign with the Raptors.
"My focus is on this year, striving to win a championship," Leonard told reporters in September. "If you look over the future, you are going to trip over the present."
He enjoyed a strong regular season for Toronto. Leonard tied for seventh in the NBA at 26.6 points per game while also averaging 7.3 rebounds, 3.3 assists and 1.8 steals across 60 appearances.
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The Raptors split the opening two games of their first-round series against the Orlando Magic. Leonard was the team's leading scorer in both contests, with 25 points in Game 1 (104-101 loss) and 37 points in Game 2 (111-82 win).
Game 3 is scheduled for Friday night in Orlando. While Leonard hasn't provided any definitive details about his offseason outlook, it sounds like an early playoff exit would hurt their cause, making the series against the Magic that much more important.