Xander Bogaerts: 11 years, $280 million through 2033
The size of Xander Bogaerts' contract was controversial when it was announced, and it continues to be a little confounding. It's undeniable that Bogaerts, the 2023 Padres' top earner, had a very good year at the plate. Even if his performance dipped slightly from his last year in with the Boston Red Sox, he still finished with a final line of .285/.350/.440 with 19 home runs.
But, like Yu Darvish, Bogaerts will be old when his contract is up — 42, to be exact — and he'll be making $25.5 million every year until then. Those are absurd numbers to ask a fan base to get behind, especially when the player has no ties to San Diego, like Bogaerts' closest comparison in Manny Machado (31 years old, $350 million over 11 years).
Clearly, Bogaerts has a lot more time to prove his naysayers wrong, but given that he's been hurt more over the past two years than his other nine in the big leagues, the threat of injury and age feels like it's looming over those kinds of opportunities.