Last Updated: October 8th, 2026 by Matthew Brown
There is no other baseball franchise that has been able to compare to the New York Yankees in terms of historic success. There is also no other baseball franchise that has been able to compare to the New York Yankees in terms of money spent on trading for superstars or signing free agents.
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Sure, the modern numbers point towards the Dodgers, but we have to put into perspective that the Yankees have been doing this ever since they spent $100,000 in a trade for Babe Ruth in 1919. That obviously worked out, but we're here to look at the ones that didn't.
11. A.J. Burnett: The $82.5 Million Rollercoaster
A.J. Burnett was a hard-throwing starting pitcher who had the stuff but lacked consistency. This was known, but the Yankees decided to give him an $82.5 million contract anyway.
It seemed like management thought he could improve with their coaching, or at least stay the same. Instead, his 3.81 ERA before he got to the Bronx became a 4.79 ERA during his three seasons there.
10. Jason Giambi: The $120 Million Disappointment
Jason Giambi was one of the most important players in the league when you considered what team he was on. The cost-conscious A's had flourished thanks to Giambi's 2000 MVP season, but he was ready for the big bucks. New York came calling to the tune of $120 million.
They expected the Silver Slugger season he had a year prior, and he delivered in his first season, but couldn't quite keep that up for the rest of his contract.
9. Roger Clemens: The Aging Rocket
I'm not denying that Roger Clemens helped the Yankees win championships. I am pointing out the fact that his Yankee years are actually the weakest for any team he played for in his career.
He did win a Cy Young, but you could also point out that he won a Cy Young in Houston four years later, after the Yankees thought he was too old for the premium price. 4.01 ERA with the Yankees is way higher than his 3.06 ERA with the Red Sox, 2.33 ERA with the Blue Jays, and even 2.40 ERA with the Astros.
8. Chuck Knoblauch: The Yips That Changed Everything
Chuck Knoblauch was a four-time All-Star when he came to the Bronx in 1998. He was a part of some championship teams, but he wasn't exactly the same Chuck Knoblauch the Yankees thought they signed.
He didn't earn a single accolade and saw his batting average dip from .304 during seven years with the Twins to .272 over four seasons with the Yankees.
7. Ed Whitson: The Pressure Cooker Casualty
One of the fastest pivots from a pickup the Yankees made was an All-Star pitcher in Ed Whitson. He was a bright spot for some rough San Francisco Giants teams.
After some time in Cleveland and San Diego, he found his way to New York. He immediately saw his ERA shoot up to the worst it's ever been, getting as high as 7.54 in 14 games before the Yankees traded him halfway through his second season with the franchise.
6. Carl Pavano: The American Idle
There is almost no explanation for Carl Pavano's luck and poor performance during his Yankee years. He had just earned an All-Star selection as a Marlin the year before he got to the Bronx.
His signing was for a little under $40 million, and they didn't even need him to be the ace. He dealt with a plethora of injuries over four years, missing one season completely, and basically wasted away on the DL.
5. Jack McDowell: Black Jack’s Bad Bet
Do you remember Jack McDowell's season with the New York Yankees? Yeah, it was short and not sweet. McDowell was a Cy Young Award winner by the time he got to New York, but the fans don't really care about past accomplishments for other teams.
They care about the here and now. McDowell went through his ups and downs and couldn't take the criticism from the home crowd one day and just flipped them off. Needless to say, that was his only season with the franchise.
4. Ken Phelps: The Trade That Lives in Infamy
In 1988, the Yankees were buyers (as usual) looking for a bat they could slot into the lineup right away. They thought Ken Phelps could be an answer, but saw that his limited versatility as a primary DH was not enough to make a difference.
He played sporadically until he was flipped around and traded the very next season to the eventual champions, the Oakland A's.
3. Kevin Brown: The Wall Puncher
The always intense Kevin Brown was a two-time ERA title winner and pretty much had a full career by the time he got to New York. Expectations were still high as he had just earned his sixth All-Star selection in Los Angeles.
Tempers got the best of him after a rough start in Baltimore, and he broke his non-pitching hand punching a wall. He could still pitch, but it wasn't the same, even if it was his glove hand.
2. Sonny Gray: Bright Lights, Big City Struggles
After a promising start to his career in Oakland, Sonny Gray was an All-Star entering his prime when the Yankees traded for him in 2017. Needless to say, his potential wasn't realized in the Bronx.
In his only full season there, he had a disappointing 4.90 ERA. The worst part is that he left New York and became a Cincinnati Red Sox in the following year, earning an All-Star selection with a 2.87 ERA.
1. Javier Vazquez: Two Times the Disappointment
This is one where the accolade could fool you. Technically, Javier Vazquez earned the only All-Star selection of his career in New York. However, he did not have a good rest of the season, as he ended that year with a high 4.91 ERA.
Then, he bounced around the league for a bit before returning to the Yankees to post an even worse 5.32 ERA. That is just a rough way to associate with an all-time franchise.
