It’s December, and that means MLB’s Hot Stove is officially heating up. The early moves-like Boston swinging a deal for Sonny Gray and Toronto landing Dylan Cease-were just the opening act.
Now we’re heading into the stretch of the offseason where front offices start making the kinds of moves that can define a franchise for years. Sometimes they strike gold.
Other times? Well, they end up with contracts that age like milk.
Take Xander Bogaerts and the San Diego Padres, for example.
After the 2022 season, Bogaerts hit free agency and left Boston behind. The Red Sox made an effort to retain their longtime shortstop, but the Padres came in with a monster offer: 11 years, $280 million.
That kind of deal doesn’t just turn heads-it resets the market. At the time, San Diego was in full win-now mode, and Bogaerts looked like a key piece of that puzzle.
Fast forward three years, and that contract is already looking like a weight the Padres may be dragging around for a long time.
Bogaerts hasn’t fallen off a cliff, but the version we’ve seen in San Diego isn’t quite the same one who made four All-Star teams in Boston. His offensive numbers have taken a step back-he’s hit just 11 homers in each of the past two seasons-and while he’s still a solid contributor, he’s no longer the middle-of-the-order force he once was.
That’s not entirely shocking. Players in their early 30s often see some decline, especially when moving from a hitter-friendly park like Fenway to the more pitcher-friendly confines of Petco Park.
But here’s the rub: the Padres are still on the hook for eight more years of this deal. Bogaerts is signed through 2033, when he’ll be 40 years old. That’s a long runway for a player whose production is already trending downward.
It’s no surprise, then, that Bogaerts’ contract landed on a recent list of MLB’s most problematic deals. While it didn’t crack the top 10, it did earn an “honorable mention” among the league’s ugliest contracts. And the reasoning is pretty straightforward: there just aren’t many people around the game who think this deal is going to age well.
The good news-if you’re looking for a silver lining-is that Bogaerts did bounce back a bit in 2025 compared to his 2024 campaign. He’s still playing solid defense at shortstop, and he remains a respected veteran presence in the clubhouse. But the offensive drop-off is real, and when you’re paying a player superstar money, you expect superstar production.
This is the kind of deal that serves as a cautionary tale for teams gearing up to spend big this winter. The talent pool is deep, and the temptation to go all-in is real. But as the Padres are learning, long-term megadeals come with serious risk-especially when you’re projecting performance nearly a decade into the future.
So as the offseason ramps up and the headlines start flying, keep an eye on the numbers, but don’t forget the context. Contracts like Bogaerts’ remind us that in baseball, as in life, timing is everything.