In the summer of 2019, Kawhi Leonard was the most coveted free agent in the NBA. Fresh off leading the Toronto Raptors to their first-ever championship, defeating a Golden State Warriors dynasty that had previously overwhelmed LeBron James’ Cleveland Cavaliers, Leonard held the league in the palm of his hand. The Toronto Raptors, Los Angeles Lakers, and Los Angeles Clippers were locked in a fierce three-way race to secure his signature. For the Lakers, pairing Leonard with LeBron James seemed like the ultimate coup to end their championship drought. However, a shocking revelation emerged: Leonard’s decision to spurn the Lakers for their crosstown rivals, the Clippers, had little to do with money or team fit—it came down to one person: LeBron James.
According to Bruce Arthur of the Toronto Star, Leonard “didn’t want to play with LeBron James, so the Lakers were a third wheel in the sweepstakes.” At the time, Leonard was at the peak of his powers, widely regarded as the NBA’s premier two-way player. His Finals MVP performance against the Warriors showcased his ability to dominate on both ends of the court, a feat that had eluded James during his second stint in Cleveland from 2015 to 2018. For Leonard, joining forces with James may have felt like stepping into someone else’s spotlight rather than carving out his own legacy.
The Lakers, desperate to build a superteam around James, pursued Leonard aggressively. James, who had joined Los Angeles in 2018 after winning one title in four Finals appearances with the Cavaliers, was seeking a co-star to restore the Lakers’ championship glory. Leonard, with his proven playoff pedigree, seemed like the perfect fit. Yet, Leonard’s reluctance to play alongside James shifted the momentum toward the Clippers.
Six years later, the Lakers’ failure to land Leonard is viewed by some as a stroke of fortune. A league executive, speaking to Lakers Daily, described the miss as a dodged bullet. “The Lakers wanted Kawhi badly,” the executive said. “Boy, they dodged a massive bullet by not landing him. You think Rich [Paul] and LeBron are hard to deal with? Uncle Dennis is even worse. He thinks Kawhi is the second coming of Jesus.” Dennis Robertson, Leonard’s uncle and top advisor, reportedly made extravagant demands during negotiations, including partial team ownership, a private jet, and guaranteed off-court endorsement income, according to The Athletic. These requests were far beyond what the Lakers were willing to entertain.
Instead of joining the Lakers, Leonard signed with the Clippers and orchestrated a blockbuster sign-and-trade with the Oklahoma City Thunder to bring fellow Los Angeles native Paul George to the team. The deal, backed by Clippers owner Steve Ballmer’s vast wealth, sent shockwaves through the league and netted the Thunder a future MVP in Shai Gilgeous-Alexander. While the move positioned the Clippers as instant contenders, it also set the stage for controversy and challenges that would later haunt the franchise.
Leonard’s tenure with the Clippers has been marred by persistent injuries and, more recently, a serious off-court issue. The Clippers are currently under NBA investigation over allegations that a $28 million endorsement deal with the now-bankrupt company Aspiration was structured to circumvent the league’s salary cap rules. A whistleblower on the Pablo Torre Finds Out podcast claimed the payments were designed to skirt NBA regulations, raising questions about the integrity of Leonard’s contract.
The Clippers have denied any wrongdoing, stating they severed ties with Aspiration in 2023 after the company defaulted on its obligations. “Neither Mr. Ballmer nor the Clippers circumvented the salary cap or engaged in any misconduct related to Aspiration,” the team said in a statement. However, the NBA’s investigation could lead to severe penalties, including fines, suspension of executives, loss of draft picks, or even voiding Leonard’s contract, per The Athletic. Leonard himself faces potential fines of up to $350,000 and may be required to repay money tied to the deal unless he can prove he was unaware of any violations.
While Leonard’s decision sent the Clippers on a tumultuous journey, the Lakers pivoted to another superstar acquisition: Anthony Davis. Acquired later that summer in a blockbuster trade with the New Orleans Pelicans, Davis proved to be the perfect complement to James. The duo led the Lakers to a championship in 2020, ending the team’s title drought and cementing James’ legacy in Los Angeles. In contrast, Leonard’s time with the Clippers has been defined by limited availability due to injuries and a lack of postseason success, with the team failing to advance beyond the Western Conference Finals.
The same league executive who praised the Lakers’ fortunate miss on Leonard didn’t hold back on the Clippers star: “The guy barely plays, doesn’t market the team he’s on, and now he’s in the news for the wrong reasons for the second time since signing with the Clippers.” Leonard’s reserved personality and frequent injury layoffs have limited his ability to elevate the Clippers’ brand, while the ongoing investigation adds further scrutiny to his tenure.
In hindsight, Leonard’s decision to avoid teaming up with LeBron James may have been a blessing in disguise for the Lakers. While Leonard remains one of the NBA’s elite talents when healthy, his injury history, controversial off-court demands, and the Clippers’ current legal troubles highlight the risks the Lakers avoided. By turning their focus to Anthony Davis, the Lakers not only secured a championship but also built a foundation for sustained success. For Los Angeles’ purple and gold, missing out on Kawhi Leonard in 2019 has aged like a stroke of fortune, proving that sometimes, the best deals are the ones that never happen.