Mark Zeigler of the San Diego Union-Tribune wrote the following in his Sunday column: "Here's what someone who knows Leonard as well as anybody told me privately: 'He's going to fall in love with Toronto—it's going to happen. He's not going to leave, I'm telling you.'"
The Raptors acquired Leonard via trade for a package that included All-Star guard DeMar DeRozan. Leonard has a player option for the 2019-20 season and can hit the open market after one campaign in Toronto.
Adrian Wojnarowski and Chris Haynes of ESPN.com noted the 2014 NBA Finals MVP "has been clear that he plans to sign with the Los Angeles Lakers in free agency next summer," although they also pointed out Raptors President Masai Ujiri acquired Leonard "with a determination that he can sell" the San Diego State product on Toronto.
The Raptors also have the advantage of being able to offer a five-year, $190 million deal to Leonard, whereas he could only sign a four-year, $141 million contract elsewhere.
While David Aldridge of NBA.com cited a source who said convincing Leonard to stay is going to be "a very tough sell," Zeigler listed a number of things working in the Raptors' favor, including a passionate fanbase, well-liked city, talented roster that no longer has to deal with LeBron James in the Eastern Conference and the presence of Leonard's former Spurs teammate, Danny Green, who came over in the same trade.
Leonard's long-term future will be a primary talking point throughout the season, but the Raptors still have a bright immediate outlook considering they were the No. 1 seed in the Eastern Conference in 2017-18 and acquired a two-time Defensive Player of the Year and two-time All-NBA First Team member to bolster their chances in the East.
Leonard can defend the opponent's best player on one end and anchor the offense on the other as someone who can shoot from deep and attack the lane, and the Raptors won't have to worry about James knocking them out of the Eastern Conference playoffs for the fourth straight time after he signed with the Los Angeles Lakers.
Toronto appears to have a shot at reaching the NBA Finals next season and keeping Leonard aboard for the future.