“I Feel Embarrassed”: Steve Ballmer Addresses Aspiration Ties, Clears the Air Over Clippers Future

After the way the past week has unfolded, many questions now surround Clippers owner Steve Ballmer. How he feels about the ongoing situation—and what it means for his future with the franchise—are just two of the most pressing. Over the last 24 hours, the former Microsoft executive has worked to prevent those doubts from spiraling into something larger. His appearance on ESPN with Ramona Shelburne was a clear attempt to address the concerns directly. If the interview felt awkward and uncomfortable to viewers, that’s because it reflected Ballmer’s own unease.

The Athletic’s Pablo Torre revealed documents alleging that Kawhi Leonard signed an endorsement deal with a company called Aspiration, a supposedly fraudulent tree-planting venture. The arrangement—described as a potential “no-show job”—has raised questions about whether it was intended to circumvent NBA salary cap rules. Adding to the controversy, Ballmer himself reportedly invested $50 million in Aspiration.

During her interview, Shelburne pressed Ballmer on the central issue: how could someone with decades of business experience and a reputation for due diligence commit such a significant investment without properly vetting the company? “I reviewed…” He began but corrected, “My staff reviewed primarily fraudulent financials.” He knows how it looks because he added, “Now, should I have sniffed it out? Maybe. I feel embarrassed and kind of silly that I didn’t sniff it out, but I didn’t.”

Aspiration filed for bankruptcy earlier this year and its co-founder pleaded guilty to investment fraud. Yet it signed Kawhi Leonard a few months later.

Ballmer didn’t deny investing in Aspiration. But explained it as a poor decision he wasn’t alone in. “I made the investment. A lot of other smart investors didn’t sniff it out either. It’s also true I’ve made a bunch of bad business deals and investments in my life, and I’ve made some good ones. This was fraud and a bad investment, and I’m embarrassed by that.”

Bad investment or not, the Aspiration ties are there. As per Torres, Leonard received $28 million from Aspiration. On the outside, allegedly the Clippers owner paid the player more by bypassing the salary cap, the second apron, luxury tax and other rules that NBA front offices are working around.

As is due procedure, the league and the board of governors will investigate. Considering the Clippers’ ownership history (Adam Silver forced the team’s sale in 2014 to save it from Donald Sterling’s scandals and Ballmer bought it in 2014), a lot of concerns loom about Ballmer and the Clippers’ future.

Steve Ballmer’s woes are far from over

The Clippers’ roster-building this offseason was almost a 9/10. They acquired Brook Lopez, Chris Paul, Bradley Beal, John Collins, and extended Kawhi Leonard. And while critics felt the roster is old, the talent on paper makes them the top contenders in the West going into the next season. It all looked peachy on the surface till Pablo Torre’s expose.

Fans have naturally not taken this lightly and want consequences if it is true. Shelburne just had ask to Ballmer, if he was an outsider in this situation, what would he have wanted the NBA to do. “I’d want the league to investigate, take it seriously. Like I said earlier, the salary cap circumvention rules are important to the league, and I’d want the league to investigate,” Ballmer responded.

Meanwhile Ballmer confirmed neither he nor the Clippers as an organization direct Aspiration to sign Leonard. “We made an introduction as is appropriate under the rules. A lot of sponsors do like to, they call it, activate by doing something also with players. We made the introduction, and that was that.”

In the aftermath of Torres’ revelation, the NBA opened an official investigation into the matter. “We are aware of this morning’s media report regarding the LA Clippers and are commencing an investigation,” NBA spokesperson, Mike Bass said on Wednesday.

The Clippers have welcomed the investigation. While the organization has taken a confident stance in its innocence, Ballmer has to also respond to the board of governors, his fellow team owners. When asked what he hopes from them, he showed some nervousness. “I don’t know. I don’t know. I hope they’ll have faith and confidence in me, the folks who’ve gotten to know me, but I can’t predict.”

While Ballmer and the Clippers are containing the publicity nightmare, an NBA investigation is a whole other matter. There is still concern about Kawhi Leonard’s and the Clippers’ statuses when the season opening is a month away. How this situation develops now depends on the NBA.