

Steve Ballmer's "Inconceivable" Donation, the $20 Million Guarantee and a Head on a Spike: Kawhi-Gate, Part V
40 snips Sep 29, 2025
Amin Elhassan, a former NBA executive turned analyst, dives into the whirlwind of Kawhi Leonard's controversial ties with Aspiration and the Clippers. The discussion unpacks the alleged salary-cap circumvention scheme and the implications of a sneaky no-show payday. They delve into Uncle Dennis's involvement and how a put option secured by a $20M guarantee played into the saga. Plus, they question Steve Ballmer’s continued funding amidst red flags and federal probes, raising eyebrows about the integrity of NBA leadership.
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Deal Looks Like Clear Cap Circumvention
- The Aspiration-Kawhi deals looked like cap circumvention because payments exceeded fair market value for no services.
- The CBA flags deals that "cannot rationally be explained" as circumvention evidence.
Aspiration Execs Called The Kawhi Deal Foolish
- Aspiration executives texted internally that a $48M deal for Kawhi was a "horrible idea" with no clear ROI.
- The CFO and CMO worried the signing was regional, redundant, and a likely overspend.
Put Option Turned Equity Into A Guaranteed Payday
- Joe Sandberg personally guaranteed a $20M equity payoff to Kawhi via an LLC and a put option.
- The put option effectively gave Kawhi a guaranteed $20M floor regardless of Aspiration's performance.