3 bad contracts the San Diego Padres will regret having on the books this offseason

They had a certain energy, a style, a groove, swagger — but it never actually turned into runs on the field. As the San Diego Padres start to regroup in the offseason, here are three contracts they might start to regret.
San Diego Padres starting pitcher Yu Darvish
San Diego Padres starting pitcher Yu Darvish / Orlando Ramirez-USA TODAY Sports
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More than maybe any other team in MLB, the San Diego Padres love to offer very long contracts of astronomical worth to players who are almost guaranteed to not be able to perform well enough in their last years to justify the money they make.

It reflects a certain inability to anticipate change, decline, or risk, a stubbornness, and an overall lack of foresight. It could be that A.J. Preller and the Padres management want to show they believe in their players and want to invest in them, which is all well and good, but it didn't do the third-place Padres much good this season.

Here are 3 contracts the San Diego Padres will regret this offseason

In 2023, the Padres were the third-highest spending team in MLB, behind both New York teams, with a total payroll of $256,045,688. Before the start of the year, they were able to lock up what looked on paper like the best lineup in baseball. They had a certain energy, a style, a groove, swagger — but it never actually turned into runs on the field. Then, an Evan Drellich, Dennis Lin, and Ken Rosenthal article from the Athletic revealed that the Padres actually had to take out $50 million in loans this year in order to be able to pay for a myriad of necessities, including player payroll.

The fact that the Padres might not even really be able to afford the following contracts makes them feel even more exorbitant and extreme. As San Diego starts to regroup in the offseason, here are three contracts they might start to regret.