Winning in the sport of basketball is everything Kawhi Leonard knew. He has always been regarded as a team player and aims to leave a legacy remembered for championships, not failures. However, Leonard has a ton of reviving to do, as the LA Clippers’ yearly shortcomings have damaged his standing among the winningest players in NBA history.
In fact, according to Crazy Stats on X (formerly Twitter), Leonard has not just dropped in the rankings but seems nowhere to be found, as the superstar is not in the top ten.
Kawhi Leonard joined the Clippers as the winningest player in @NBA history (min. 300 games played, including playoffs).
He’s now outside the top 10. pic.twitter.com/hPZ5a9yHB1
— Crazy Stats (@NBAcrazystats) December 11, 2025
This portrays a ridiculous drop-off and sums up the story of Leonard’s tenure in LA: losses, missed windows, and failures that will always be remembered.
Thus, Leonard has another full season left on his contract, and the Clippers will not be winning much in 2025-26. For him to climb back where he once was, after several additional tolls will inevitably lower his career winning percentage, the two-time champion needs a trade.
Kawhi Leonard will be working hard deep into his 30s to claim the title he once had
In 2019, Kawhi Leonard was at the top of the mountain with the most wins combining the regular season and playoffs, ever, as a professional. This is mind-boggling, but when the math is done, it all makes sense.
Two championships already equal a number of postseason wins; taking into account his successes with the legendary San Antonio Spurs squad led by Tim Duncan, Tony Parker, and Manu Ginobili, the only player who could have been number one was Leonard.
The Clippers signed a certified winner, and by logic, Leonard should have at least three rings, and LA should have one.
However, it has been so long since Leonard made it out of the first round as a Clipper that some fans cannot even remember. He has essentially formed a habit of losing, even if LA has had high-standing regular seasons.
Additionally, the players around Leonard in the list of the NBA’s all-time winningest players are mostly retired. Names that may ring a bell include Magic Johnson, Larry Bird, and a few Spurs legends like Duncan and Ginobili.
That said, Leonard notably lost the throne, and some of the blame lies in how unwatchable the Clippers have been this season. He has never been part of a team that has lost 19 of its first 24 games, as 12 of his 14 seasons have led to some type of playoff run, and in the other two, he was injured.