It’s the middle of summer, and while Major League Baseball charges through its season, one man who hasn’t picked up a bat in over two decades is still hitting home runs financially.

Welcome to another Bobby Bonilla Day.

Every July 1, former MLB star Bobby Bonilla receives a check for exactly $1,193,248.20 from the New York Mets — a payment that will continue every single year until 2035, when Bonilla turns 72. That’s right: Bonilla hasn’t played professional baseball since 2001, yet he’s set to earn nearly $30 million in total, long after his retirement.

We were just trying to make a smart decision Bonilla’s agent Dennis Gilbert once said. Turns out it became a historic one.

The Deal That Keeps Paying

So how did this incredible payout come to be?

Back in 1999, the Mets wanted to part ways with Bonilla, who still had $5.9 million left on his contract. Instead of paying it outright, then-owner Fred Wilpon opted for a deferred payment plan — heavily influenced by his faith in his investments with financier Bernie Madoff.

Wilpon assumed the money would grow in Madoff’s fund, but unbeknownst to him, that fund was actually a Ponzi scheme, one of the most notorious in history. Madoff, who died in 2021 while serving a 150-year prison sentence, defrauded investors of billions.

https://x.com/cnnsport/status/1940013774846545946Meanwhile, Bonilla’s agent struck a deal to start deferred payments in 2011, with a guaranteed 8% annual interest. That one clever clause turned a $6 million settlement into a jaw-dropping $29.8 million payday.

It’s a gift that keeps on giving,” fans often joke every July 1 — and it’s no exaggeration.

Not Alone in Deferred Deals

While Bonilla’s arrangement is perhaps the most famous, he’s far from the only athlete enjoying the benefits of deferred money.

Take Shohei Ohtani, for instance. When the Los Angeles Dodgers signed the two-way sensation in 2023 to a $700 million deal over 10 years, Ohtani agreed to defer $680 million of it. That means, beginning in 2034, Ohtani will receive $68 million per year until 2043 — long after his contract ends.

It’s a strategy teams like the Dodgers have embraced, also using it to structure deals for Blake Snell and Tommy Edman.

But the idea isn’t new. It dates back to the 1960s, when accountant Ralph Dolgoff helped the American Basketball Association (ABA) lure players away from the NBA with long-term financial security through staggered payments — a model now known as The Dolgoff Plan.

A Cautionary Tale and a Financial Legacy

Bonilla’s situation, while humorous to many, underscores a deeper lesson in sports business: timing and smart negotiation can be more valuable than short-term payouts.

His story is often brought up in sports contract discussions MBA programs, and financial planning courses. It’s a blueprint for how players can turn smaller amounts into massive financial windfalls with the right strategy — and the right agent.

In a world of monster contracts big trades, and short careers Bonilla’s yearly check remains a curious reminder that sometimes not playing pays the most.