Many months before the fractures that led to Leonard's departure from San Antonio began to surface, Popovich approached Pippen and asked him to speak to Leonard after a Spurs-Bulls game in Pippen's hometown of Chicago.
"Kind of get a feel because he felt like that his game patterned my game a little bit," Pippen said, speaking Friday during a guest appearance on ESPN's The Jump.
A day after Leonard made his first homecoming to San Antonio as a member of the Toronto Raptors, Pippen said the two-time Defensive Player of the Year and 2014 Finals MVP has improved on things the Hall of Famer had noticed before their meeting.
"I kind of admired his game and told him I'd been watching him and could see he's been getting better and better," Pippen said. "And things I felt like he could work on to become even a better player. And I felt like he's filled all those voids."
Things went sour between Leonard and San Antonio last season when there was a disagreement over how to handle the tendinopathy in his left quadriceps that bothered him throughout 2017-18. Leonard wound up playing only nine games with the Spurs -- none after mid-January -- and missed San Antonio's five-game loss to the Golden State Warriors in the first round of the Western Conference playoffs.
Sources have told ESPN's Michael C. Wright that Popovich and Leonard have kept in touch since the player was traded to Toronto in July. In November, after Popovich made headlines with comments on Leonard's leadership, the sources said the two remained solidly in touch via text messages.
"They won a championship there," Pippen said. "He was the MVP. And as Pop said, sometimes in your career things go differently."
On Thursday night, after the Raptors' 125-107 loss to the Spurs, Leonard had a long hug and conversation with Popovich at center court. Popovich began talking to Leonard, then told television cameras to get away from them and the two moved closer to San Antonio's bench.
But Leonard was booed any time he was involved in the game -- from player introductions to the final buzzer.
"I feel like it's mended between Coach Pop and Kawhi," Pippen said. But "obviously" the fans weren't part of that, the former Bulls star added.
Pippen, speaking to ESPN's Rachel Nichols and Amin Elhassan, said his meeting with Leonard gave him the impression the two-time All-Star's public persona accurately reflected his personality.
"It was hard," Pippen said. "He did speak, but as you guys know, Kawhi's a very quiet player, so he doesn't speak much off the court, either. But it was great just to sit down and talk to him."
Information from ESPN's Tim Bontemps was used in this report.