It is July 1st, and while much of the baseball world turns its attention to trade rumors and All-Star snubs, a curious little tradition unfolds in New York—one part financial farce, one part baseball folklore. It is Bobby Bonilla Day. The day when the 62-year-old, who last played for the Mets in 1999, collects his annual check for $1,193,248.20 from the organization that, through a peculiar blend of poor timing and blind faith in Wall Street wizards, ensured his name would live in sports infamy long after his playing days ended.

The origin story has been told often, but it never loses its bite. In 2000, the Mets, eager to part ways with an aging Bonilla and convinced they were financial geniuses thanks to their cozy ties to Bernie Madoff’s house of cards, agreed to buy out the final $5.9 million of his contract. But rather than a clean payout, they struck a deal dripping in irony—25 years of annual payments with 8% interest, stretching all the way to 2035. The thinking? Madoff’s promised double-digit returns would cover the whole thing, and then some. The reality? Well, here we are.

But the Mets, it turns out, aren’t alone in this strange corner of baseball economics. Deferred money is as much a part of the sport now as sunflower seeds and seventh-inning stretches. From Bret Saberhagen quietly cashing checks to Manny Ramirez still collecting from the Red Sox, the practice has become a financial sleight of hand for teams chasing flexibility and players chasing guaranteed security. Even the mighty Dodgers, flush with cash and World Series aspirations, embraced the model this winter with Shohei Ohtani’s jaw-dropping $700 million megadeal, $680 million of which won’t touch his bank account until 2034.

The contrasts between Bonilla’s deal and Ohtani’s couldn’t be more stark. One is the product of a team cutting its losses on an underperforming veteran. The other? A strategic masterpiece designed by baseball’s most marketable global superstar, giving the Dodgers short-term cap relief while Ohtani essentially prints money down the road. But both, in their own way, reflect a sport where the ink on a contract may dry, but the consequences linger—sometimes for decades.

Perhaps the most delicious layer to the Bonilla saga? Even in retirement, his name sits atop the pay charts, out-earning some of baseball’s brightest young stars. Players like Pete Crow-Armstrong, Paul Skenes, and Riley Greene—all producing at a high level for fractions of Bonilla’s annual haul—can only marvel at the arrangement. It’s a reminder that in baseball, talent and timing are everything, but sometimes, timing alone is worth seven figures.

​​So, as Mets fans share wry smiles and the checks continue to clear, Bobby Bonilla Day marches on—a quirky, cautionary, and undeniably entertaining chapter in baseball’s never-ending contract chronicles. And with a decade left on the deal, the legend of Bobby Bo isn’t going anywhere anytime soon.