Nobody expected the Clippers’ gamble on Kawhi Leonard to end with federal investigators, leaked documents, and whispered talk of salary-cap circumvention. Yet here they are. On Jan. 3, 2025, Leonard was supposed to be out. Hours later, he suited up anyway, dropped 25 points after the All-Star break, and still couldn’t keep Los Angeles from bowing out to the Denver Nuggets in seven games. By September, the rumors had hardened into an NBA probe into the team’s ties to a $28-million endorsement deal with Aspiration, a financial-services company now mired in a federal fraud case. Clippers owner Steve Ballmer himself had sunk $50 million into the firm, but the pursuit was never just this simple. 

The investigation has revived old stories about the extraordinary lengths the Clippers took to land Leonard in 2019.  According to reporting by ESPN’s Baxter Holmes, Leonard’s uncle and adviser Dennis Robertson pushed for unprecedented concessions: partial ownership stakes, private air travel, guaranteed off-court income, and a strict media-silence policy around the forward. The Clippers declined the most extreme requests but still reshaped the organization around Leonard’s preferences: allowing a helicopter commute from San Diego in his first season, scaling back his public obligations, and, most dramatically, surrendering Shai Gilgeous-Alexander and a cache of first-round picks to acquire Paul George as his co-star. It was the most ambitious swing in franchise history, and for a time, it appeared to work.

To outsiders, it looked like the ultimate power play; to some inside the league, it felt like a gamble with no safety net. Former Spurs and Lakers star Pau Gasol summed up that tension recently when he told ESPN: “Kawhi, when I played with him in San Antonio, he was one of the greatest players in the league…and then the way he exited San Antonio was quite not ideal, and it created some issues around our season at that time. But there were some differences that couldn’t be solves and he got his way out. The Raptors benefited from that, and they won a championship, and they were very happy about that. Here the Clippers took a big gamble. (But) It didn’t quite pan out as they planned.…Now they have to deal with the reality and what’s there in front of them, and looking forward at what’s best for the franchise. ” Gasol’s words hit at the heart of the Clippers’ $293M dilemma.

Leonard came to Los Angeles in 2019 as the ultimate prize:  fresh off a championship in Toronto and carrying the kind of leverage only a Finals MVP can wield. On paper, the Clippers went all-in to land him: they gave him a three-year, $103 million deal with an opt-out after the second season, then mortgaged their future to pull Paul George out of Oklahoma City, surrendering Shai Gilgeous-Alexander and a mountain of first-round picks. 

Leonard was at his peak: averaging 27 points, 7 rebounds, and nearly 5 assists in his first season in L.A., then following up with 25-6-5 in 2020-21 and 28 a night in the 2020 playoffs. The Clippers looked like contenders every time he was on the floor. By 2021, Leonard had re-upped for four more years at $176 million, and in 2024, he tacked on another $152 million extension.  But, at the same time, injuries have been a constant thorn for Kawhi.

 That right ACL tear in the 2021 playoffs wiped out the entire 2021–22 season, and since then, setbacks just kept coming. Meniscus tear in 2023, knee inflammation cutting short both 2023–24 and 2024–25 seasons, plus sprains to his ankles, groin, adductor, and hips. Altogether, he’s missed nearly 290 regular-season games over eight years. 

George was coming off a career-best season, finishing third in MVP voting with 28 points and 8.2 rebounds per game when he stepped into LA. He got his own blockbuster deal but bolted for Philadelphia in 2024. On top of that, the Clippers’ 2019 trade still stings. 

Shai Gilgeous-Alexander, who was part of the deal that brought Kawhi and George to LA, has soared in Oklahoma City, winning a championship and locking in a $285 million supermax, while LA struggled without first-round picks for four straight years.

All told, the injuries piled up, the depth vanished, and the George-Leonard partnership never yielded the deep postseason runs. Steve Ballmer’s franchise poured nearly $300 million and a half-decade of planning into a duo that never could justify the gamble… and now that long-held patience might just be wearing thin.

Steve Ballmer’s patience tested?

Amid the investigation, Ballmer denied any wrongdoing, telling ESPN, “The allegations have not been true,” yet questions flared after minority owner Dennis Wong invested $1.99 million just before Aspiration sent Leonard a delayed $1.75 million payment. ESPN’s Baxter Holmes added, “Multiple GMs and other league executives said they expect Leonard to play out his contract with the Clippers… But even then, one former staffer said, ‘‘They’re done building around [Kawhi]. They know that and he knows that.’” 

Now, Former Clippers strength coach Randy Shelton has joined the ongoing investigation, adding fuel to the fire. With injuries, controversies, and financial questions piling up, it’s no shock that the Clippers are expected to eventually cut ties with Leonard. It’s something that even Pau acknowledges, 

“At some point relationships end, terms end. So Kawahi, just like any other player will be, moving on, and the Clippers have to deal with what’s best for them, and they should be optimistic and positive going into a season,” said Pau.