When Nico Harrison traded Luka Dončić to the Lakers in February 2025 for very little in return—a move compared by many as one of the worst trades in NBA history—it sparked widespread criticism. The Clippers’ later acquisition of Kawhi Leonard in 2019 might now rival or even surpass that trade as an all-time disaster, particularly when viewed purely as straightforward transactions.
Leonard’s tenure with the Clippers, which appears to be concluding with his imminent trade to Toronto after a two-month delay, was marked by disappointment over seven seasons. During that time, Leonard was paid nearly $350 million but managed to help the team win only three playoff series, never advancing beyond the second round. His career with the Clippers was plagued by injuries, missing the entire 2021-22 season following an ACL tear and playing just 37 games in the 2024-25 season. His postseason return after the ACL injury was cut short due to a meniscus tear, contributing to three consecutive first-round exits.
The Leonard deal itself was a major failure for the Clippers, but the broader picture worsens when factoring in the costly Paul George trade—done at Leonard’s insistence—which brought no championship to L.A. In exchange for George, the Clippers gave up five first-round picks (including one used for All-NBA player Jalen Williams), two pick swaps, and future two-time MVP Shai Gilgeous-Alexander to the Oklahoma City Thunder, who ended up winning the 2025 championship. Combining Leonard and George’s salaries, the Clippers paid nearly $600 million over the years for a pair that failed to reach a single conference finals together.
On Wednesday, the NBA imposed severe penalties on the Clippers following a year-long investigation into salary-cap violations involving Leonard. The league found the Clippers orchestrated off-court income deals between Leonard and companies linked to the team, facilitated endorsement agreements, induced companies to enter those agreements by offering team business, covered Leonard’s personal expenses, and failed to properly report these illicit activities. Essentially, the Clippers created off-the-books side agreements to circumvent league salary rules, resulting in hefty consequences.
While Leonard reportedly earned over $50 million in these covert deals and faced only a minor $700,000 fine, the Clippers felt the full force of the league’s punishment. They were fined $30 million, with owner Steve Ballmer and business president Gillian Zucker suspended for a year, and president of basketball operations Lawrence Frank suspended for six months—all unpaid. Most damagingly, the Clippers forfeited five consecutive first-round draft picks from 2029 to 2033, a crippling blow in an era where draft capital is crucial for team building.
Taking into account both the George trade and the penalties, the Clippers effectively sacrificed 10 first-round picks, two star players (including MVP Shai Gilgeous-Alexander), years of executive leadership, and $30 million in fines—all for the chance to field a Leonard-George duo that ended up falling short by every measure. Though signing Leonard back in 2019 seemed like a smart basketball move—George was coming off a stellar MVP-contending season—all the extra under-the-table deals backfired spectacularly.
Looking at the Mavericks, who traded Dončić away, they surprisingly landed Cooper Flagg and likely benefited from falling into the 2025 lottery, winning the number one overall pick with just a 1.8% chance. This turn of events makes the debate over who is more valuable over the next decade—Dončić or Flagg—a fair and open one. Meanwhile, the Clippers are left struggling to recover from their organizational mistakes and significant losses. Even factoring in two first-round picks received from the Raptors (who are relieved the Leonard deal might be reversed), the Clippers still have a net loss of eight draft picks. Unlike the Mavericks, they have no top-tier young talent to show for their missteps.
In the end, Kawhi Leonard’s time with the Clippers has cost the organization far more than his on-court value ever justified. Owner Steve Ballmer must be regretting partnering with Leonard, as the financial and basketball repercussions continue to unfold.
Fan Take:
This saga is a stark reminder of how even the most promising player acquisitions can backfire drastically when compounded by bad management and rule-breaking. Clippers fans and basketball watchers alike should watch closely—this fallout reshapes team-building strategies and the importance of integrity in managing star talent in today’s NBA.
Source: www.cbssports.com
