Padres fans will cringe when they see which two contracts made the 2028 nightmare list

Every team has that one contract that they regret handing out. Usually, a player who at the time looked promising and was feeling inclined to sign them to a long-term deal. While some stand out to many, it is hard to keep up with all of these bad contracts, and that’s why Bleacher Report predicted the league’s worst contracts leading up to 2028.

Unfortunately for the Padres, a pair of their own players both landed in the top two of these rankings. We’re talking about Xander Bogaerts (#1) and Manny Machado (#2), who are both inked to long-term contracts that expire simultaneously in 2033.

Machado, 33, signed a ten-year, $300 million contract with the Padres in 2019 that would keep him under contract through 2029. However, Machado signed a new eleven-year, $350 million contract, adding four more years of team control and keeping him around through 2033.

Manny Machado and Xander Bogaerts named on a 2028 contract nightmare list

In the seven seasons Machado has played with the Padres, he has been solid, slashing .275/.340/.485 with an OPS over .800. But with his age climbing, the production will likely take a hit. Could you imagine paying Machado nearly $40 million in his age-40 season? Absolutely not.

Bogaerts, on the other hand, has already seen a decline in production since signing an eleven-year, $280 million deal in 2022. While he started strong in his first season with the Padres, batting .285 with a .790 OPS, the numbers fell off in 2024, where he failed to get his OPS above .700 (.688). Bogaerts improved a tad in 2025, but it remains a question of whether he can be a valuable asset to the Padres' lineup in the future.

Fernando Tatis Jr. (fourteen-year, $340 million) and Jackson Merrill (nine-year, $135 million) were also named on the list as honorable mentions, as both are under contract into the 2030s. But Tatis has continued to be one of the league’s best, while Merrill is still incredibly young.

It will be interesting to see how Preller reflects on these past decisions down the road.