Sometimes, Losing Is the Winning Move

Sometimes, it pays more to lose.

On September 13, 2025, Canelo Alvarez participated in a boxing match with Terrence Crawford. Crawford beat Canelo by unanimous decision. The payouts?

Crawford (winner): guaranteed $10 million.

Canelo (loser): guaranteed—take a deep breath—$150 million.

Why?

Because losers serve a purpose—they bring the audience, they bring the viewers, they make the match happen.

Turns out, that now applies in financings too.

When Tropicana faced its liquidity squeeze this year and needed new financing, it negotiated with both its existing lenders and third-party lenders, like TPG Angelo Gordon.

Here’s the crazy part: though it lost in its bid, TPG still got paid. In other words, the loser won a fee—and a big one at that.

These compensation structures, while not yet the norm, signal a marked shift in the post-liability management financing arena and Noetica‘s data shows these structures are increasing. Lenders’ argument is simple: if I’m going to stand in the ring and take the hits, only to hear a negative decision when it goes to the scorecard, I need a guaranteed purse.

For borrowers, third-party proposals serve as a powerful lever to extract discounts, extend maturities, or secure lower coupons from existing lenders. Strong ‘deal away’ threats by the borrower could even be used to exact concessions from existing parties.

The only one that seems to be losing: the winners.

While losing may not be free anymore, only time will tell how lucrative it becomes. And for all you winners out there, well, here’s my advice: sometimes, it pays more to lose.