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Worst Yankee free agent signings in the last 10 years

With Free Agency off to another slow start and the Winter Meetings just a few days away, it got me thinking about moves the Yankees have made in previous years.

The Yankees are always known to make a splash in free agency, and whether the moves pan out or not, it’s always interesting to watch it unfold. This article will take a ride down memory lane at the worst free agent signings the Yankees have made in the past 10 years. There are plenty of names to throw around, but there are a select few that stand out from the crowd. To keep it fair, this will only include players whose contracts have expired.

Kevin Youkilis

Did you remember Youkilis was a Yankee? If not, it’s understandable. Following the 2012 season, the former Red Sox 3B signed a one year/$12 million deal to be the 3B. At the time, it did not seem like a bad signing. A-Rod was going to miss a chunk of 2013 with an injury and Youkilis was two years removed from an All-Star appearance. Unfortunately, this did not pan out. Youkilis was on the DL before the season even began with a back strain. He returned May 30 just to be put back on the DL two weeks later with the same back strain, which later on turned out to be a herniated disc and it kept him out the rest of the season. Overall, he appeared in 28 games with the Yankees and hit .219.

Pedro Feliciano

Here’s another one we all forgot about. The former Met reliever came to the Yankees in 2011 on a two year/$8 million deal. The lefty specialist was heavily relied on with the Mets. He appeared in 344 games between 2007-2010. He ranks 2nd all-time in Mets history for games pitched with 484. Unfortunately, the Mets constant usage of the reliever hurt the Yankees. Feliciano was shut down in early 2011 with shoulder soreness, which later turned out to be a torn anterior capsule and rotator cuff in his throwing shoulder.

The injury required surgery and sidelined him for the rest of the 2011 season and most of the 2012 season. Feliciano appeared in Double-A ball for the Yankees in 2012, however, he never made one appearance in the majors during his time with the Yankees.

Although it was a small deal, having $8 million go down the drain for absolutely nothing in return is the reason Feliciano is on this list.

JA Happ

When the Yankees re-signed Happ for $34 million over two years, I couldn’t believe my eyes. He had a solid 2nd half with the Yankees, but not good enough in my opinion to warrant $17 million a year.

In 2019, he regressed. His ERA rose from 3.65 in 2018 to 4.91 in 2019 as well as his WAR dropping from 3.0 to 1.3 in the respective seasons. Also, his FIP increased from 3.98 to 5.22. Happ provided depth to the rotation in 2018, but in 2019 and 2020, he was nothing more than a liability to the team. In the 2019 playoffs, he did not make one start. Happ only appeared in relief in three games and pitched a total of 3.2 innings. In 2020, he appeared in Game 2 of the ALDS after the questionable call by Aaron Boone to pull Deivi Garcia after one inning. As we all know, Happ gave up four runs in that game.

This signing looks much worse when you realize Charlie Morton and Lance Lynn both signed for less money in the same offseason. Morton received a two year/$30 million deal with Tampa while Lynn left the Yankees and signed a three year/$30 million deal with Texas.

Lynn has exceeded expectations in Texas so far. In 2019, he pitched over 200 innings for the first time since 2014. He posted a 3.67 ERA with a 3.13 FIP, but the biggest change for him was that he got his walk issue under control. His BB/9 in previous years was always around 3.50 BB/9. In 2019, it dropped to 2.55 BB/9, which is about the average for the league. This subsequently increased his K/9 to a career high 10.63.

Morton continued to perform in Tampa posting a 3.05 ERA with a 6.1 WAR and a 0.90 ERA in 2019. Most importantly, Morton showed up in October and was a big factor to the Rays postseason success in 2020. In four starts, he allowed seven earned runs.

Happ is a veteran pitcher and it looks much worse when Boone has to constantly skip his starts with hopes that would help him get back on track. For $17 million a year, that should have never been the case.

Jacoby Ellsbury

You knew it was coming. This was by far the worst contract the Yankees gave out in the past 10 years. I won’t lie, when the Yankees signed him, I was ecstatic. Ellsbury was the one Red Sox I always enjoyed watching and thought he would help this team a lot. Needless to say, I was completely wrong.

Ellsbury signed with the Yankees following the 2013 season for *sigh* seven years/$153 million. In 2014, he saw his production dip a bit, but still had a respectful season having a slash line of .271/.328/.419 and had a WRC+ of 109 and 3.6 WAR. In the following seasons, injuries plagued him.

Ellsbury appeared in 111 games in 2015. In 2016, he played in 148 games and had a WRC+ of 90 and a 1.8 WAR. It was clear he was not the same player anymore. Ellsbury last appeared in a game in 2017. He was rehabbing from a torn hip labrum, but experienced several setbacks which never got him back on the field. Following the 2019 season, the Yankees released Ellsbury and put an end to that (dreadful) era.

Ellsbury’s contract will go down as one of the worst in team history.


Let’s hope the history of giving out bad contracts is behind us. Free Agency should be picking up in the next few weeks and expect the Yankees to make a few moves. Next week, we’ll end on a high note as I will talk about the best signings the Yankees have made in recent years and hopefully by then, they will have signed a free agent or two as well.

Tweet me @sashalueck and let me know anyone I missed or your thoughts on these players!