Yu Darvish: 6 years, $108 million through 2028
Yu Darvish is one of those guys with a massive contract and high risk attached, especially because at 37, he's the oldest of the five Padres who have contracts keeping them in San Diego for five or more years. He signed a six-year extension in February 2023, meaning he'll most likely be with the Padres until he's 43 years old. There was one 43-year-old in MLB this year: Rich Hill, who was making $8 million with the Pirates before he was traded to the Padres and then placed on waivers.
Whether or not Darvish's performance has declined so much by 2028 that his team will place him on waivers, he'll still be making $18 million. In August of this year, he went down with an injury in his right elbow. He's been on the IL multiple times throughout his tenure in the major leagues, most frequently with elbow and hip issues. Before that, he was having the second-worst year of his career. He finished out with a 4.56 ERA and an fWAR down to 2.4 from 4.1.
Maybe this is ungenerous. It could be that Darvish just had an off year. Pitchers who are 40 and up, while rare, can be very effective in relief roles. But Darvish is not getting any younger, and he's never going to make any less money than the Padres have already promised him over the next five seasons to perform in a starting role. All in all, the Padres might go into the offseason wishing they had more money to give some of their 15 arbitration eligible players, and might wish they gave Darvish less.