5 biggest free agency and trade misses in modern Yankees history

3. Bryce Harper (Free Agency)

There’s not a single Yankees fan out there who had doubts about Bryce Harper coming to the Bronx back when the slugger was a Washington National. This was the quintessential Yankee once upon a time. The most hyped prospect of our time. And he delivered. Rookie of the Year. MVP.

Only problem? The Yankees had Aaron Judge in right field, so when the 2018 offseason arrived, there seemingly wasn’t a fit. But there’s always a fit for a player of Harper’s caliber, and his 13-year, $330 million contract actually ended up not being as crippling as many expected. Harper will make only $22 million per season in his age-36-38 campaigns. Not bad.

But because of the Giancarlo Stanton acquisition a year prior, there was no way the Yankees were putting another $300 million contract on the books while also creating a logjam in the outfield. Though Stanton’s come around since the 2020 playoffs, the Yankees acquiring him was a bit of a mystery at the time. He had a well-documented injury history and was slated for the DH role sooner rather than later. Instead of waiting a year for Harper, they traded for Stanton, and then used Stanton’s contract as an excuse not to spend big on the next star-studded free agent class (not even Patrick Corbin?!).

In a perfect world, you simply sign Harper and make it work. Say goodbye to Brett Gardner. Trade Aaron Hicks. Whatever you have to do, you do it. Harper is on his way to becoming a future Hall of Famer and the Yankees surely could’ve figured out a way to make him a roving outfield option if they were serious about planting Judge in right field ( … even though they weren’t because he played center field in 2021).

Historic miss here.