That’s according to ESPN’s Ryen Russilo, who claims Lowry is still bitter about Toronto trading away his best pal DeMar DeRozan.
The Lowry-DeRozan relationship came to an abrupt end last summer when the Raptors traded away the latter for Leonard.
It was a move seen as a huge gamble with Leonard set to become a free agent at the end of the season.
The trade drew comparisons to what the Oklahoma City Thunder did with Paul George, who were able to convince the 28-year-old to re-sign in the offseason.
Toronto will be hoping they can do the same with Leonard this summer, although the Lakers, Clippers and Knicks have all been linked with a move for the two-time All-Star.
Part of the reason OKC were able to convince George to re-sign with them was due to the recruitment work Russell Westbrook did, and that will likely fall on Lowry to do the same with Leonard.
However, Russillo states that the point guard is still hurt by losing DeRozan last summer that he will not try to copy Westbrook’s approach.
“I don’t think it’s going to work,” Russilo said on Jalen & Jacoby.
“I had Woj on my podcast and Woj doesn’t like speculation but his quote on my podcast was that ‘Toronto still have a lot of work to do here’.
“I think one of the biggest problems for Toronto, is that Lowry is not going to recruit Kawhi Leonard to stay in Toronto.
“The reason Paul George stayed in OKC, where nobody really thought he would, is that Westbrook recruited him.
“Paul George is an impressionable guy, he likes Westbrook and he get him to stay.
“So Kyle Lowry, who is still upset that his buddy DeRozan got traded – for a better player and they have have a better chance of finally coming out of the East after failing five times together.
“He’s upset that the guy who couldn’t get them out of the playoffs as his buddy in the backcourt is gone, so that’s he’s not actually going to help the franchise keep Kawhi.
“That’s an insane, different problem that is unlike what other teams normally have is that guys ‘no you have to stay here’ and it doesn’t seem Lowry feels that way.”
He added: “Even if you get out of the East, I don’t think you’d sit there if you’re Kawhi and think, ‘wow, we’re loaded’.
“What we’ll never know, and Kawhi is a hard guy to figure out, is that he might wake up every day, ‘this is nice, Toronto’s nice, this is cool, but I can’t wait to go back to L.A. and maybe it’s the Clippers’.”