Pablo Torre Finds Out

Episode: Steve Ballmer, the Other Cuban and the $118 Million Infusion: Kawhi-Gate, Part IV

Date: September 18, 2025
Host: Pablo Torre
Co-Host: Dan Le Batard

Episode Overview

This episode is the fourth part of Pablo Torre's deep-dive exploration into “Kawhi-Gate”—the saga revealing an alleged clandestine attempt by Steve Ballmer (LA Clippers’ owner), his affiliates, and the now-defunct fintech "green bank" Aspiration to funnel tens of millions to NBA superstar Kawhi Leonard. Torre investigates whether these transactions constituted the most elaborate salary-cap circumvention scheme in sports history, navigating leaks, denials, and new documentation. The episode also unpacks the ongoing public feud with Mark Cuban and the roles of other NBA power brokers, while using new evidence and testimonies to follow the money with increasing granularity.

Key Discussion Points & Insights

1. Setting the Scene: Journalism Under Fire

• [03:13] Dan Le Batard observes that many journalists and public figures “don’t want [Pablo’s] reporting to be true,” despite its exhaustive documentation and legal vetting.

  “Your standard is one that, that is much higher than the people who are denying the story.”
  — Dan Le Batard (03:32)

• Torre highlights the unprecedented scrutiny and legal review surrounding this reporting.
• Mark Cuban (not present on the episode) is referenced as the main public skeptic, repeatedly critiquing Pablo’s story and demanding increasingly impossible standards of proof.

2. Timeline and Anatomy of the “Scam”

• Wire Transfers & Payments:

  • Dennis Wong (Ballmer’s college roommate and Clippers co-owner) wires $1.99M to Aspiration—his first ever green bank investment—right after being warned Aspiration was collapsing.
  • Nine days later, Aspiration wires $1.75M to Kawhi Leonard’s company, KL2 Aspire, as part of a $28M secret endorsement deal—with minimal deliverables.
  • The pattern: Aspiration receives sudden infusions from Ballmer-affiliated entities just before deadlines to pay Kawhi.

• Aspiration’s Company Health:

  • By the time Kawhi gets paid, Aspiration’s earlier $300M raise (including Ballmer’s $50M) is almost entirely depleted on operating expenses, legal fees, and “flagrant” marketing spending.

  “All that [cash] is gone. It’s gone so quickly. It’s gone, in fact, before Kawhi Leonard ever got paid.”
  — Source Number One / Aspiration Finance Exec (25:40)

3. Following the Money: Carbon Credits as Cap Circumvention

• [27:02] Mark Cuban had tweeted questioning why more wasn’t made of the Clippers’ “millions of dollars in carbon credits” purchases, positing this could itself be a way to funnel value to Kawhi via inflated deals at Aspiration.

• Torre reveals exclusive documents:

  • [29:02] Clippers letterhead, signed by the CFO, approving a $21M withdrawal to Aspiration for “carbon projects,” just two weeks before Kawhi’s first payment due date.
  • Additional wire transfers: $3M on April 1, then $32M on April 4, totaling at least $56.4M in prepaid credits from the Clippers that spring, synchronizing with Kawhi’s expected payments.

  “The LA Clippers prepaid a grand total of at least $56,403,462 on carbon credits from Aspiration in the spring of 2022 alone. Tracking alongside Kawhi Leonard’s payments.”
  — Pablo Torre (34:10)

• Source confirmation:

  • Former Aspiration finance execs confirm this is exactly the sort of flow Cuban himself theorized would constitute cap circumvention.

  “They did that. I mean literally. He described one of the few ways that the Clippers and Ballmer got money into aspiration.”
  — Source Number Two / Aspiration Finance Exec (31:36)

4. Internal Disagreement within Aspiration

• [16:15] Three former senior execs (CFO, CLO, CTO) sign a statement to Torre confirming discomfort at the size and opacity of the Kawhi deal, saying it was presented by CEO Andre Cherny as a “completed arrangement” with “significant objections.”

  “The Leonard deal was presented to the company as a completed arrangement and executed by Mr. Cherny despite significant objections from members of the senior management team... It was strategically difficult to justify then and it remains so today.”
  — Statement from Roger Avenisian, Mike Shukrona, Eric Anderson (16:21)

• Cherny, in correspondence, continues to deny it was a “no-show” contract, sidesteps definitive answers by citing memories and legal privilege.

5. Ballmer and Wong’s Ongoing Capital Infusions

• [48:23] Contrary to public statements that their relationships ended when Aspiration defaulted, Torre demonstrates that Ballmer personally invested another $10M via his LLC in March 2023—when it was widely known the company was floundering, and layoffs were underway.

• In total, $118M funneled over 18 months from Ballmer, Wong, and the Clippers organization.

  “September 2021 to March 2023, Team Ballmer...proceed to give a grand total of $118 million to aspiration in 18 months. Each new payment, I would argue, less defensible than the last.”
  — Pablo Torre (58:21)

• Ballmer’s defense (from a recent event): he and the Clippers were “defrauded” and all conduct was “independent” and within NBA rules. He “welcomes” the NBA investigation.

  “I was personally defrauded through our interactions with the company...Our relationship with the company and our players’ relationship with the company were independent...I feel quite confident in that, that we abided the rules.”
  — Steve Ballmer (57:00)

6. League Oversight and the NBA’s Response

• [62:26] NBA Commissioner Adam Silver claims he only learned of the scandal from Pablo’s podcast.

  "I'd frankly never heard of the company Aspiration before and I'd never heard a whiff of anything around an endorsement deal with Kawhi or anything around engagement with the Los Angeles Clippers."
  — Adam Silver (62:26)

• Documents show the $300M sponsorship (including Clippers jersey patch) required NBA approval, per explicit contract language, yet there’s ambiguity on how deeply the league scrutinizes such funding flows.
• Silver (at a public forum) signals concern about “competitive fairness,” not ruling out deeper review.

  “What we do want to pledge to our fans is that from a league office standpoint, we treat everybody the same...we care deeply about competitive fairness in this league. And that's what this issue potentially touches on, which is, I think, why, in part, it's getting so much attention.” — Adam Silver (66:51)

7. Dramatic Deposition: Co-founder Takes the Fifth

• [41:50] In a 2024 video deposition relating to a $278M civil judgment, Aspiration co-founder Joe Sandberg pleads the Fifth Amendment only when asked about dealings with the Clippers—after openly confirming relationships with other celebrity investors (Drake, DiCaprio).

  Q: “In fact, at one point, Aspiration had a deal with the Clippers, did they not?”
  A: “I assert my Fifth Amendment rights.”
  — Joseph Sandberg (41:50)

• Sandberg later identifies Ballmer and Wong as the only new investors during the key period, with other firms declining.

8. Insider Testimony: Widespread Internal Alarm and Rapid Turnover

• [23:21] Former finance staff describe a toxic atmosphere, repeated internal investigations, and near-immediate departures of execs who raised questions about missing funds and suspicious outflows.

  “Shorter than milk, which is abnormal...They could not hire a full time controller and they could not hire a full time CFO.”
  — Source Number One / Aspiration Finance Exec (23:21)

9. The NBA’s Structural Dilemma: Can Ballmer Be Held Accountable?

• [69:56] Le Batard and Torre discuss the awkward power relationship—Silver is functionally subordinate to owners; Ballmer’s wealth effectively insulates him unless other owners mobilize as they had in the Donald Sterling case.

  “He's not actually the boss of Steve Ballmer, that Steve Ballmer is the boss of Adam Silver.”
  — Dan Le Batard (67:59)

Notable Quotes & Memorable Moments

• On the Reporting’s Resistance:

  “It's weird to make it clear that there’s something here, but you know what? As always, all you gotta do is stick around after the break.”
  — Pablo Torre (12:49)

• On Internal Executive Pushback:

  “I don't remember conversations about the NBA salary cap.”
  — Andre Cherny, former CEO, via email (15:09)

• On the Documentation:

  "Something with the Clippers logo signed off by the CFO of the company. Like, that's pretty strong documentation."
  — Dan Le Batard (32:00)

• About Ballmer’s Continued Investments:

  “Ballmer invested $10 million more at a $23 share price. Over 23. So more than double what he invested...when the company was actually publicly in a good financial state.”
  — Source Number One / Aspiration Finance Exec (55:13)

• On Adam Silver’s Difficult Position:

  “I don't know what Adam Silver's supposed to do here, either publicly or privately. I feel like he's a bit boxed in...it's ridiculous that the arbitration that involves Roger Goodell would be heard by Roger Goodell...it's a little bit of a similar circumstance with Silver and Ballmer.”
  — Dan Le Batard (67:59)

• Game Clue Analogy:

  “I feel like I'm living inside of the game Clue where we have the Clippers CFO with the 21 million dollar carbon credit deal in the conservatory...”
  — Pablo Torre (37:42)

Important Segment Timestamps

| Timestamp | Segment / Topic Description | |-----------|----------------------------| | 03:13 | Dan Le Batard discusses industry reluctance over Pablo’s reporting | | 07:03 | Mark Cuban’s public skepticism and Twitter activity | | 16:21 | On-the-record statement from three former Aspiration execs | | 25:40 | “All that is gone”: cash flows and early warnings | | 29:02 | Reveal: $21M Clippers-to-Aspiration carbon credits letter | | 34:10 | Summary of over $56M in carbon credit prepayments | | 41:50 | Joe Sandberg’s deposition: pleads the Fifth on Clippers deal | | 48:23 | Ballmer invests another $10M in Aspiration, contradicts team statement | | 55:13 | Ballmer invests at a $23 share price amid collapse | | 62:26 | Adam Silver’s initial response to the scandal post-podcast | | 63:12 | Sponsorship agreement clause showing NBA review obligation | | 66:51 | Silver’s live comments on league fairness and the investigation | | 69:56 | Owners' influence over league discipline; Ballmer’s insulation |

Tone & Narrative Flow

The tone is briskly journalistic yet irreverent—Pablo and Dan riff with familiarity but return repeatedly to the gravity and potential fallout of the saga. Both draw on years of sports, media, and business experience to contextualize revelations. The banter, use of dramatic re-creations (the Sandberg deposition), and callbacks to ongoing Twitter drama with Mark Cuban make this a uniquely entertaining, idiosyncratically transparent, and rigorously sourced investigation.

For Listeners Who Haven’t Tuned In

This episode offers damning documentation and live testimony tracing how $118 million flowed from Ballmer and his affiliates to Aspiration in highly suspicious synchrony with secret compensation to Kawhi Leonard—possibly circumventing NBA salary rules. The hosts present new, never-disclosed primary sources; depositions where company executives go silent; and signatures from Clippers c-suite confirming multi-million-dollar transactions. Pablo and Dan trace how these maneuvers slipped past league oversight and set in motion the NBA’s highest-profile sports business scandal since Donald Sterling.

If you’re interested in media investigations, league politics, or just cutting through sports-industry gaslighting, this episode is the essential pivot point in the “Kawhi-Gate” series.

End of Summary