15 most expensive contracts in MLB history and how they turned out

3. MLB contracts: Aaron Judge, NYY – $360M/9 years

Number three on our list comes from this past offseason. Aaron Judge was perhaps the most followed free agent saga of the winter.

Despite persistent rumors of a move to the west coast, the 2022 MVP eventually re-signed with the New York Yankees, inking a nine-year, $360M deal, one of the biggest MLB contracts ever. Going into his age-31 season, Judge will finish the contract as a 39-year-old.

Judge bet on himself last winter, turning down the Yankees’ extension offer. He certainly cashed in by having his first fully healthy campaign since 2017 and forcing the team to offer him the third-most expensive MLB contract in history.

The 6-foot-7 right fielder mashed the ball last season. He slashed .311/.425/.686 and led the majors with 62 homers, 131 RBI, 133 runs scored and a 211 OPS+.

It’s hard to say how the deal will work out for the Yankees, as Judge is an elite talent when healthy. But there are some red flags from his injury history that the team may not get full value from the three-time Silver Slugger.

Judge missed time in 2016 and 2019 with oblique strains and 50 games in 2018 with a wrist injury. In 2020 he had two stints on the IL due to a calf strain after dealing with a cracked rib and collapsed lung before the season. While he didn’t miss much time in 2021, lower body soreness plagued him early in the year.

If Judge can stay healthy, he’ll give the Yankees what they paid for, at least for the next few years.