Yankees worst free agent contracts ever handed out

When the Yankees released Jacoby Ellsbury on Nov 21 — still owing him $26 million over the next two seasons, he joined a list of tumultuous mistakes the Yankees have made in free agency.

With how much cash the Yankees have, they can push the envelope on a deal harder than any other organization. But like a teenage girl splurging at Kendra Scott, there is bound to be a couple of cases of buyers remorse among the successful purchases.

There are some curious cases when it comes to Yankee contracts. Obvious ones come to mind, such as A.J. Burnett. Yes, his 5-year, $82.5 million contract was hefty, and he had an overall shaky time in the Bronx.

But when he was truly needed, he would rise to the occasion, just like his brilliant one-run game in Game 2 of the 2009 World Series. Compared to the others, at least Burnett helped secure some silverware. And when Burnett got going, his knuckle-curve was near untouchable.

However, it’s cases like Burnett that are swept under the rug and forgotten, and wisely so, but they serve as mistakes to learn from, especially for the GMs. So let’s unearth these miscues and take a look at the worst free-agent contracts in Yankees history.