3x All-Star Speaks in Kawhi Leonard & Steve Ballmer’s Defense Despite New $10M Controversy

The Los Angeles Clippers are no strangers to high-stakes drama, but the latest storm brewing around Kawhi Leonard’s $28 million “no-show” endorsement deal with a now-bankrupt environmental startup—Aspiration—has thrust owner Steve Ballmer’s aggressive spending habits into the NBA’s crosshairs. Former Aspiration employees, speaking anonymously to the “Pablo Torre Finds Out” podcast, alleged the 2022 agreement was a blatant salary-cap workaround, funneling off-the-books cash to Leonard without triggering league penalties.

The Clippers, still stinging from a first-round playoff flameout against the Denver Nuggets in May, now face questions that could overshadow their Intuit Dome era: Is Ballmer’s win-at-all-costs ethos a virtue or a violation? The Clippers fired back with a fiery statement: “Neither the Clippers nor Steve Ballmer circumvented the salary cap. The notion that Steve invested in Aspiration to funnel money to Kawhi Leonard is absurd.” Ballmer himself doubled down in an ESPN interview, insisting he knew nothing of the deal’s details and welcoming the scrutiny: “I’d want the league to investigate [if it were another team]. Take it seriously.”

Enter Gilbert Arenas, the former All-Star turned podcaster, who has emerged as Ballmer’s unlikely defender amid the uproar. “I commend him,” Arenas said of Ballmer. “You’re spending money to try to win. I’m not gonna hold you for that. You shouldn’t hold him for that.” His point was clear: while the Clippers’ maneuvering may look suspicious, it reflects the cost of competing under the NBA’s new system.

Arenas doubled down, saying these moves are inevitable. “With this new second-tier b——- they got going on, you best believe that there’s going to be other deals. There’s gonna have to be a lot of deals under the table so it doesn’t get into that second tier.” In his eyes, Ballmer isn’t an outlier, but the first to push the envelope.

Arenas shrugged off the backlash, framing the Clippers’ alleged tactics not as cheating, but as a logical response to the NBA’s punishing new collective bargaining agreement. The 2023 CBA’s second apron—projected to loom around $195 million for 2025-26, slaps teams with brutal restrictions: frozen draft picks, trade limitations, and an inability to aggregate salaries or sign buyout players. For a payroll behemoth like the Clippers, hovering near that threshold with Leonard, Paul George (before his offseason exit after 2023-24), and James Harden, it’s a straitjacket on ambition.

His cohost, Josiah Johnson, humorously echoed the sentiment, comparing the NCAA’s pre-NIL days: “The rules are meant to be broken. We grew up in a pre-NIL college world where we’re getting bags broken. But we see the stories. We see n—– driving Escalades on 24s that they can’t afford. We don’t ask questions. We just say, ‘Good job, sir.’”

Arenas is not the first person coming to the Clipper’s defense. Mavericks minority owner Mark Cuban dismissed the notion that the Clippers’ owner would risk his franchise over Leonard’s deal. “I just don’t see Steve giving up $50 million and risking his entire reputation, integrity, and franchise,” Cuban said, framing the investigation as misplaced. He emphasized that, in an NBA board governor’s meeting, deliberately violating the CBA would be “like murder,” underlining how unthinkable it would be for an owner to jeopardize billions in investments over a side payment.

But the allegations are getting sharper. Recent follow-up reports show new details: Kawhi Leonard’s endorsement deal with Aspiration, claimed to be worth $28 million through cash payments, is also said to include an additional $20 million in stock, bringing the total promised to around $48 million.

Bankruptcy filings list Leonard’s LLC, KL2 Aspire, as a creditor owed $7 million. Another wrinkle: Clippers minority owner Dennis J. Wong reportedly invested nearly $2 million into Aspiration just nine days before the company wired $1.75 million to Leonard’s business. This payment had already been delayed. On top of this, a new revelation surfaced that Steve Ballmer invested almost $10M into the company in 2023, after they had already declared financial troubles.

As the investigation unfolds, the Clippers’ situation intersects with ambition and risk. Ballmer has never been shy about spending, but the scrutiny could stretch beyond Los Angeles with Kawhi Leonard under intense spotlight.

New $10M Twist Deepens the Clippers’ Troubles

What initially seemed like a questionable endorsement now looks like part of a tangled financial web. Court filings show that in March 2023, Steve Ballmer poured nearly $10 million into Aspiration, just months after his vice chairman Dennis Wong invested close to $2 million. That timeline matters: Wong’s stake was quickly followed by a $1.75 million payment to Kawhi Leonard, and Aspiration was already missing payments on Leonard’s four-year, $28 million deal.

The revelation, first detailed by The Athletic, links Ballmer directly to a firm now mired in bankruptcy, fraud charges, and a federal probe into its former CEO. Leonard, meanwhile, remains listed as a $7 million creditor, raising fresh doubts about how much of his deal was ever fulfilled.

Combined with Ballmer’s earlier $50 million infusion into Aspiration in 2021, shortly after the Clippers struck a $300 million arena sponsorship with the company, the additional $10 million fuels suspicion that the team blurred the line between business and basketball.

The NBA’s investigation, led by the law firm Wachtell, Lipton, Rosen & Katz, will determine whether these payments amount to cap circumvention or simply bad business. Commissioner Adam Silver has said he’s looking for more than “the appearance of impropriety,” but with fraud indictments, missing money, and Ballmer himself claiming he was “conned,” the optics alone are damaging. For a franchise chasing its first championship, the fallout could be severe.