New York Yankees: Five free agents that failed in the Bronx

Brian Cashman has hit the jackpot during his tenure as New York Yankees General Manager when it comes to signing free agents. He also has had some misfires that have not worked out. From pitchers to position players, there have been some signings that he would like a do-over with.

Below are five free agents signings that just never worked out for Cashman and the Yankees since 1998.

5. Kevin Youkilis

What a one-year, $12 million disaster. Signed in December of 2012, Kevin Youkilis inking a short-term deal didn’t seem that bad at the time. Signed to play third base with Alex Rodriguez having hip surgery, things went downhill fast. Very fast.

He suffered a back injury early in the season and tried to play through it. He couldn’t and it ended badly. Playing in only 28 games in 2013 with a .219 batting average, he had season-ending back surgery in June and never played again for the Yankees. He went to Japan the following year, where he finished his injury-plagued career.

4. Kyle Farnsworth

Looking for a setup guy in front of Mariano Rivera, Cashman took a shot with the hard-throwing Kyle Farnsworth in 2006 with a three-year, $17 million contract. Things never really worked out for Yankees and Farnsworth.

In 2006, he went 3-6 with a 4.36 ERA in 66 innings. One year later, he went 2-1 in 64 appearances with a 4.80 ERA. After his struggles continued into 2008, the Yanks traded him to the Detroit Tigers for veteran catcher Ivan Rodriguez. He might have been the biggest set-up bust in the Rivera era.

3. Carl Pavano

Coming off a playoff finish in 2004 that was a nightmare, to say the least, Cashman was looking to upgrade the starting pitcher over the winter. He was able to beat out the Detroit Tigers and Boston Red Sox when he landed Carl Pavano four years and $39.95 million.

Over the four years in the Bronx, Pavano seemed to spend more time on the DL than he did on the mound. In 26 starts over four years, he went 9-8 with a 5.00 ERA in 145.2 innings. His 2005 season was cut short in June with a rotator cuff injury that kept him out for a year and a half. After Tommy John surgery early in the 2007 season, he came back midway through 2008 and had a 5.77 ERA in seven starts. The end of the 2008 season finally ended his stint as a Yankee.

2. Kei Igawa

A left-handed pitcher from Japan, Cashman and the Yankees paid $26 million just to negotiate with Kei Igawa. After negotiations, Igawa and the Yankees agreed to a five-year, $20 million deal in December of 2006. Safe to say, things would never end up working out.

Igawa pitched a grand total of 71.2 innings for the Yankees, with 67.2 of those innings in 2007. He gave up 76 hits, 47 earned runs, 15 home runs, walked 37 and struck out 53. From there, he spent time in the minors, mainly with Scranton unless the Yanks needed a spot-starter or had a doubleheader. To think the Yankees paid him $20 million over five years to pitch in Triple-A.

Cashman tried unsuccessfully to move on from Igawa multiple times, finally cutting ties following the 2011 season when his contract expired.

1. Jacoby Ellsbury

The first four years of the Jacoby Ellsbury era in New York wasn’t too bad after signing a seven-year, $153 million contract in the winter of 2013. He had a .264 batting average with 39 home runs, 198 RBIs and 102 stolen bases.

Then in early 2017, things changed. He suffered a concussion making a catch in a game early in the season. He would miss a month before returning and ending up on the bench because of the play of Aaron Hicks and Clint Frazier. In 2018, Ellsbury missed the season with an oblique strain and hip ailment, before choosing to have surgery and ending his season before it started.

Last season, he never played a game or dressed for a game, after a foot injury and a shoulder injury shut down his season and career as a Yankee. In November, the Yankees released Ellsbury with two years remaining on his contract.

There are more signings that could have been on this list, but these five are five that stand out.