5 worst contracts in New York Yankees history
The New York Yankees have been accused of buying their championships since George Steinbrenner purchased the team back in 1973. While that may not be the case any longer since his passing, the Yankees will still spend as needed.
Those contracts are always a gamble. No one knows if those deals will work out, even with an established player coming on board. Injuries, a poor fit, age, or any variety of factors can lead to even the best hypothetical deal not working out.
The five worst contracts in New York Yankees history
As the Yankees have historically spent a great deal in free agency, there are plenty of contracts to consider. Some have hit. Others, such as the ones below, have not and were complete disasters.
Let’s take a look back at the first worst contracts in New York Yankees history.
5. Ed Whitson
Ed Whitson was a solid pitcher from a small town in Tennessee, a country boy who liked a relatively quiet life. However, when the New York Yankees came calling with a five year deal worth $7 million, he could not say no.
That signing was a disaster from the start. Whitson and New York did not mesh at all. He clashed with manager Billy Martin with the two eventually getting into a fight at a bar following a gam. Whitson and his wife would receive hate mail and death threats, with fans waiting to heckle him outside the stadium after the game, even when he did not pitch.
It eventually got to the point where Whitson would have a nervous breakdown if he had to pitch in Yankee Stadium. He refused to take off his warmup jacket, no matter how hot it was, so that fans wouldn’t see his number when he was in the bullpen. Finally, after just a year and a half, he was sent back to the Padres for Tim Stoddard.
Somehow, despite those issues, Whitson managed a 15-10 record with the Yankees. The problem was that it came with a 5.38 ERA and a 1.641 WHiP over his 195.2 innings. Those numbers would have been even worse if Whitson did not manage to throw two complete game shutouts with the Yankees as well.
Ed Whitson and the New York Yankees were a bad match from the beginning. This deal was doomed to failure before the pen hit the paper.
4. A.J. Burnett
The New York Yankees signed A.J. Burnett in the hope that he would lead them to a championship. He did just that in 2009, sort of.
Burnett was not the ace that the Yankees had hoped for in 2009, but his 4.04 ERA was better than league average. While he led the league with 97 walks, he also struck out 195 batters in his 205 innings. His start in the ALDS, where he allowed one run in six innings, was one of the highlights of his season.
His last two years in pinstripes were brutal. Burnett had a combined 5.20 ERA and a 1.472 WHiP in his 377 innings. He allowed an identical 109 earned runs in both seasons, posting a 21-26 record. That five year, $82.5 million deal was a disaster, with the Yankees shipping him to Pittsburgh after just three years.
That change was exactly what Burnett needed. Although he still battled with inconsistency, he went right back to being a top of the rotation caliber arm. After a rough season in Philadelphia, Burnett returned to Pittsburgh for one final season before retiring.
A.J. Burnett was a solid, albeit inconsistent, pitcher. The high pressure environment of the New York Yankees only made it worse.
3. Jacoby Ellsbury
There was no question about Jacoby Ellsbury‘s talent. The question was whether or not he could stay on the field.
While he was a noted speedster, and the type of player that the New York Yankees needed, there was a question about what he was exactly. He had a 30-30 year in 2011, but had never reached double digit homers in any other year. Despite enough red flags for a May Day Parade, the Yankees gave him a seven year, $153 million contract.
Ellsbury was a disappointment when he did play, posting a subpar .264/.330/.386 batting line in his 2171 plate appearances. He hit just 39 homers and 86 doubles while stealing 102 bases. However, that production was not the worst part of Ellsbury’s contract.
He did not play at all in the final three years of the deal. He had hip and back issues that sidelined him for the entire 2018 season, with his hip eventually requiring surgery. That recovery, and subsequent setbacks, led to his missing the 2019 season as well. He was released prior to the 2020 season, and due to the pandemic, was the second highest paid player in the majors as he received his full salary. A $5 million buyout of a team option for 2021 finally got Ellsbury off their books for good.
Jacoby Ellsbury was a major question mark when he was signed by the New York Yankees. His injury problems reared their head and made that deal a disaster.
2. Carl Pavano
There were times where one had to wonder if Carl Pavano collected his paycheck from the New York Yankees wearing a ski mask and holding a gun.
Pavano had been a solid middle of the rotation arm prior to signing with the Yankees. He had made over 30 starts for three consecutive years and had made his first All Star Game in 2004. As he was 28 years old, it seemed as though the Yankees were getting a solid pitcher for the rest of his hypothetical prime.
It is important to note that Pavano had made at least 30 starts in each of the three years prior to signing with the Yankees. That is because he made a grand total of 26 starts in his four years in pinstripes, with 17 of those coming in 2005. His numerous injuries, including a strained butt that caused him to miss the entire 2006 season (seriously) and a car accident he only told the organization about on the day he was scheduled to pitch, ruined his tenure.
In exchange for that four year, $39.95 million contract, Pavano posted a 9-8 record with a 5.00 ERA and a 1.455 WHiP. He struck out 75 batters with 30 walks in his 145.2 innings as he made over $1.5 million per start. Naturally, once he left the Yankees, he found his form once again until injuries forced him to retire.
The New York Yankees thought they were getting a key piece for their rotation in Carl Pavano. Instead, they landed someone who just could not get on the mound.
1. Kei Igawa
Making moves just to match another team tends to lead to disaster. Such was the case when the New York Yankees signed Kei Igawa in response to the Red Sox landing Daisuke Matsuzaka.
While Matsuzaka never lived up to the hype, Igawa was an unmitigated disaster. He signed a five year deal worth $20 million, with another $26 million as a posting fee. In exchange, he made a total of 16 appearances in pinstripes, posting a 6.66 ERA and a 1.758 WHiP in his 71.2 innings.
He pitched perfectly well in the minors, with a 3.83 ERA and a 1.304 WHiP in his 533 innings, striking out 419 batters with 163 walks. The problem was that Igawa was not being paid to be a solid minor league arm, even though he spent his last three seasons in the organization in Double-A and Triple-A.
To make matters worse, Igawa refused to go away. The Yankees twice attempted to sell his contract back to a team in Japan, but he refused to head back. His banishment to the minors did nothing to change his mind as he spent the full five years of that deal stateside.
dark. Next. Banuelos back with Yankees
The New York Yankees thought they had the answer to Daisuke Matsuzaka in Kei Igawa. Instead, they received a solid minor league arm.