The Yankees have spent big money on several free agents in recent years and a fair amount of those large contracts didn’t work out the way the team hoped. Let’s take a look at some of the worst free-agent signings the Bronx Bombers have made in the last 25 years.
The New York Yankees have a storied tradition of winning and excellence throughout their history. However, despite their 27 World Series championships over the years, the Yankees haven’t always made the most sound signings in free agency.
On Wednesday, the Yankees cut ties with one of their worst free-agent signings ever as they cut ties with outfielder Jacoby Ellsbury. New York released Ellsbury with more than million remaining on his contract. Ellsbury struggled and was injured for much of his time in New York and the organization was ready to move on from the situation.

Carl Pavano

Wright didn’t exactly have stellar career numbers before he had a career year with the Atlanta Braves in 2004. The veteran right-hander went 15-8 with a 3.28 ERA with the Braves and the Yankees decided to sign him to a three-year, million contract. Unfortunately for the Yankees, Wright reverted back to his old ways as he went 5-5 with a 6.08 ERA in his first season in the Bronx. During his tenure with the Yankees, Wright went 16-12 with a 4.99 ERA

Kei Igawa

Most remember Kevin Youkilis for his time with the Boston Red Sox. However, Youkilis signed a one-year, million contract with the AL East rival Yankees in 2013. In just 28 games during his lone season in New York, Youkilis hit .219 with two home runs and eight RBI in a season that was cut short due to a back injury.

Jaret Wright

The Yankees had quite a bit of luck when it came to trotting out Roger Clemens over the years. The right-handed pitcher came back for one final go-round in 2007 when he signed a one-year, .7 million contract in 2007. However, Clemens didn’t exactly look like the “Rocket” of old as he went 6-6 with a 4.18 ERA in his final MLB season. He did register his 350th career win in his final season, but that was one of the few bright spots during this brief contract.

Kevin Youkilis

The Yankees struck out in 2008 when the franchise signed AJ Burnett to a five-year, .5 million contract. Burnett had previously enjoyed success with the Florida Marlins and Toronto Blue Jays, but wasn’t exactly the big-game pitcher that the Yankees envisioned. He put together a 34-35 record with a 4.79 ERA in three seasons and was traded to the Pittsburgh Pirates in 2012.

Jacoby Ellsbury

In 2002, Jose Contreras defected from Cuba and inked a four-year, million contract with the Yankees. Contreras did get off to a strong start in his first year with a 3.30 ERA and 7-2 record. However, the right-hander ended up with a 4.64 ERA during his time with the club. Contreras was inconsistent and only lasted two seasons in the Bronx before he traded to the Chicago White Sox during the 2004 season.

A.J. Burnett

Pavano signed a four-year, .95 million contract in 2004 with the Yankees after having a career year with the Florida Marlins the previous season. The right-hander started off his Yankees tenure strong with a 4-2 record in his first 10 starts, but it was all downhill after that. Pavano suffered a shoulder injury that season and landed on the disabled list. In addition, Pavano missed the entire 2006 season after going down in spring training. When it was all said and done, Pavano put together a 9-8 record with a 5.00 ERA in just 26 games during his Yankees tenure and signed with the Cleveland Indians the following offseason.

Roger Clemens

This one is the freshest in the minds of Yankees fans. During his six years with the Yankees, Ellsbury hit .264 with 39 home runs, 198 RBI, and 102 stolen bases in 520 games. Ellsbury has seen the past two seasons taken away due to injury and never really lived up to the hype surrounding him when New York signed him away from the Boston Red Sox on a seven-year, 3 million deal ahead of the 2014 season.

Kenny Rogers

The Yankees signed Rogers to a four-year, million contract, but it wasn’t exactly a match made in heaven. Rogers went 12-8 in his first season with the Yankees, but recorded a 4.68 ERA, which was the second-worst of his career up to that point. Rogers ended up going 18-15 with a 5.11 ERA during his two seasons in New York. He was then traded to Oakland.

Jose Contreras

In 2006, the Yankees took a big chance by paying a million posting fee to negotiate a contract with Japanese pitcher Kei Igawa. New York ended up signing Igawa to a five-year, million contract and let’s just say it didn’t exactly work out. Igawa had just a 2-4 record to go along with a 6.66 ERA in 16 total games with the Yankees. He had all of the accolades during his time in Nippon Professional Baseball, but nothing translated to the MLB. In 2008, Igawa failed to make the team out of spring training.