The New York Yankees have probably the highest expectations of all sports teams. Every season, if the Yankees don’t make the playoffs, it’s pretty much considered a failure. With having 27 championships, expectations are always going to be high, which means the front office year after year needs to make sure they have a talented team that can handle taking this team constantly to the postseason. It seems like it would be an easy job, as you would think you can just pay the best players a lot of money and you’re guaranteed a playoff spot. But, it doesn’t always work that way.
The Yankees have been known for overpaying players that don’t produce, or letting go of players too soon. Sometimes it’s too tempting to sign a player to a big contract after they excelled in another league or had a good season or two, but rushing to that commitment doesn’t always work out. And then there’s other times where players may be in a bit of a funk, or aren’t given enough time to produce to their full ability, and then are let go. Not only have the Yankees released quite a few star players, but they have traded them away or let them go into free agency without giving them what they deserve. Running the front office is a difficult job, especially for the most famous sports team in the world, which is why some of these bad decisions have been made.
15 Never Should've Let Go: Chris Carter
The Yankees have been looking for the replacement of Mark Teixeira ever since he retired. It seems like they’re looking to have that first baseman perform up to high standards immediately, but with any sport, it takes time to progress. At the beginning of 2017, the Yankees signed Chris Carter, formerly with the Milwaukee Brewers. Carter just came off a huge year where he hit for 41 home runs and 94 RBIs, so obviously the Yankees had high expectations for him. Well, in a Yankees uniform, he only hit 8 home runs and 26 RBIs, with a .201 batting average.
The Yankees cut his first season short as they released him midway through the season, giving him no time to progress. Now, no one knows what the future will be like for Carter, but a team could land themselves a stud if he turns out to play how he did in 2016 again.
14 Held Too Long: Hideki Irabu
Talking about the dead isn’t always a fun topic, but unfortunately, Hideki Irabu had to make this list. As we wish his life was long-lived, Yankees fans may have wished his career in the Bronx didn’t last as long. Irabu was a star in Japan, and after a short time with the San Diego Padres before the 1997 season, he demanded that he only play for the New York Yankees. Well, Irabu got his wish, but did the New York Yankees get theirs? He only played three seasons with the Yankees, but after his first season it may have been too much.
In his first season with the Yankees, he went 5-4 with a 7.09 ERA. Batters were figuring him out, and he wasn’t able to adjust. From there the Yankees should have let him go, but he got more chances. He played another two years, and finished his Yankees career with a 29-20 record and a 4.80 ERA. Although his numbers weren’t terrible, they weren’t what the Yankees would have hoped.
13 Never Should've Let Go: Vernon Wells
Age is always a big factor when it comes to signing players, but Vernon Wells deserved some more time. There’s a chance that if the Yankees were in to bring Wells back for a longer term, maybe we would have seen a few more years in pinstripes. But without hesitation, the Yankees let him go. Wells had a plan of always retiring after his big contract, but he worked so well with the Yankees, that maybe he would have continued playing ball. But Wells could have been a valuable part to this team, even in the back end of his baseball career. In the final season of his career, he hit 11 home runs and had 50 RBIs, with a .233 batting average. For a guy who was in his mid-30s, he played pretty well.
12 Held Too Long: Phil Hughes (P)
There was a lot of talk at one point that Phil Hughes was going to be the new ace of the New York Yankees. Fans loved seeing him at spring training knowing there was a bright future for him, and he just never lived up to what he was supposed to be. Maybe the way the fans felt about him and what they expected of him, led to him having a longer leash. Hughes lived for seven seasons with the Yankees, but that was too long for what he deserved. He finished out his Yankee career going 56-50 with a 4.53 ERA. Only once in his Yankee career did he have an ERA that was below 4.00. He was kind of just all over the place, and finally years after he should have been done, the Yankees gave up on him after he went 4-14 and had a 5.19 ERA in 2013.
11 Never Should've Let Go: Ivan Nova
Maybe it was the pressure that was too much for him, or maybe we’re giving him too much credit. Ivan Nova was never a star pitcher for the Yankees, and he may never have been one in his career. But Nova pitched decently well each year, which led to why he had such a long career with the Yankees. There were definitely things Nova had to work on after he struggled to start the 2016 season with the Yankees, but after the trade to Pittsburgh, Nova pitched pretty well. He finished the 2016 season off with the Pirates going 5-2 with a 3.06 ERA. His total win-loss record after the season completed with both seasons was 12-8. Nova was inconsistent for sure, but there were many games that Nova pitched pretty hard, and was able to keep his team in the ball game.
10 Held Too Long: Joba Chamberlain
Joba Chamberlain’s career will go down as one of the weirdest careers of a Yankee player. Joba went from on top of the world, all the way down to the bottom. Maybe it was Joba getting figured out, or maybe it was the fact that the Yankees switched him from a relief pitcher to a starting pitcher. He had a good season in 2008, going 4-3 with a 2.60 ERA. But after that, his ERA began to rise and he started to lose more games. It only took another season for the Yankees to realize he wasn’t a starting pitcher, but then he began to start struggling when coming in for relief. It seems that the Yankees messed with something that didn’t need to be messed with. And maybe, they should have realized earlier that Joba was not who he once was.
9 Never Should've Let Go: Carlos Beltran
The Yankees really needed more of a spark in that lineup besides Aaron Judge. Well, before there was Aaron Judge, there was Carlos Beltran. Beltran struggled in his first season with the Bronx Bombers, but then began to hit the ball out of the park, and became very consistent. His batting average in his last two seasons were .276 and .295. Beltran would have been an excellent complement to Judge. With a young team that could have made the World Series this season, Beltran would have been the perfect veteran in the dugout, and also some extra power in a lineup that struggled.
There also would have been less pressure on Beltran considering how well Judge played this past season. Although Beltran did struggle in the 2017 season, he did help contribute to the Astros’ World Series championship.
8 Held Too Long: Carl Pavano
He's the player that every Yankees fan absolutely hates talking about. He's the man whose four-year deal worth $39.95 million turned out to be a complete bust. Because of not only his performance, but injuries, Carl Pavano should have been gone in year two. Pavano was supposed to be the future of the Yankees, and possibly even their new ace. He lasted two and a half seasons, before the Yankees traded him to the Cleveland Indians.
He never really played like a star, so it was pretty shocking that the Yankees treated him like he would become one. He never succeeded in pinstripes, and to this day, he’s known as one of the worst contracts in New York Yankees history. Sometimes, this front office has too much confidence in players before they give them a reason to have that confidence.
7 Never Should've Let Go: Curtis Granderson
The Yankees definitely did Curtis Granderson wrong. After a great four years in New York, it wasn’t enough to get Granderson a big contract to stay in the Bronx. Granderson was a slugger who also was a great fielder. Maybe it was due to the fact that in his contract year he got hurt, and only ended up playing 61 games. But if you take that season out of the equation, Granderson was hitting like a MVP. Two of the seasons he was in New York, he actually hit for over 40 home runs. Granderson was good for one more good contract, as he played really well even with the Mets. And the Yankees would have signed an outfielder who would be able to him lead the young guys, making it easier for them to carry this team into the future.
6 Held Too Long: A.J. Burnett
There’s a lot of people that believe that A.J. Burnett couldn’t handle the pressure of pitching in New York, and it definitely showed. Burnett signed a big contract at the same time that Mark Texieira and C.C. Sabathia signed their big contracts, which was the year they won the World Series. But Burnett was not a big part of helping this happen, as he struggled nearly his whole career with the Yankees.
After his second season when he went 10-15, the Yankees should have sent Burnett out of New York. It was clear that he couldn’t deal with the pressure of playing for the Yankees, because he drastically played a lot better when he moved over to the Pirates. Burnett was a huge expense, but one that the Yankees could have gotten rid of a little bit earlier.
5 Never Should've Let Go: Hideki Matsui
If you have a star player that stays loyal to you and becomes a role model for fans, you stay loyal right back. Unfortunately, the Yankees couldn’t stay loyal to Hideki Matsui. Now, this could have gone both ways. But usually players who are loyal to their team that depart, usually aren’t getting what they deserve, and there’s a very good chance Matsui wasn’t getting a contract he deserved after a huge 2009 season where the Yankees won the World Series. Matsui was one of the better hitters of this generation, as he never had a batting average below .270. He was more than just a baseball player, he was a legend of the Yankees organization. The Yankees should have done everything in their will power to make sure that Hideki Matsui would never play a game wearing another uniform.
4 Held Too Long: Jacoby Ellsbury
His time as a Yankee isn’t over yet, but it should have been. The Yankees signed Jacoby Ellsbury an absolutely terrible deal, worth $153 million for a seven-year deal. Contracts like that are given to stars, but Ellsbury has not played anywhere near a star level status. We're not sure what the Yankees were expecting, but he hasn’t been able to duplicate that same level we saw that he was at in 2011. With the level Ellsbury is currently playing at, the Yankees could find a much younger and cheaper option.
To put into comparison Ellsbury’s contract, Brett Gardner is playing at twice the rate that Ellsbury is playing, and is currently about a third cheaper of the contract. Ellsbury’s contract is definitely up there for one of the worst in franchise history. It’s about time this Yankees team finds a way to move on from this contract, and Ellsbury.
3 Never Should've Let Go: Melky Cabrera
The Yankees kind of gave up on Melky Cabrera, before he ever hit his prime. It could be discouraging to want to sign a guy to a long-term contract when you don’t see enough production, but Melky turned out to be a pretty good ball player. Known for his speed, bat, and ability to play the field, he’s a threat all around. After leaving the Yankees, Cabrera began to continuously put up double digit home run numbers year after year, and even improved on his batting average. It seems like every year Melky keeps getting close to having a .300 batting average. Now this makes it more sense to show why the Yankees should have never signed Jacoby Ellsbury to that big contract. Melky is currently making around $15 million a year, and playing at a higher level.
2 Held Too Long: Alex Rodriguez
Alex Rodriguez may go down as one of the best baseball players we have seen in recent time, but the way the Yankees handled this situation was terrible. In the middle of the season, Rodriguez seemed to basically have been forced to either retire, or he would have been released by the Yankees. No going away party, no appreciation, no nothing. After 2011, it may have become more evident that Rodriguez was on the decline of his career.
Now if you want to stay loyal to him and let him play out his career, fine. But the way the Yankees went about this situation, it probably would have been better if they released him and let A-Rod make the call on his own. It seemed to become a bad breakup, and it ended what seemed was a great relationship in the Bronx. Maybe if the relationship ended earlier, it would have ended on better terms.
1 Never Should've Let Go: Robinson Cano (2B)
This definitely had to be the worst decision the Yankees made recently. The Yankees expected that Cano would start to decline while receiving a huge contract in Seattle, but maybe not. Cano has played an impressive ball game since he got to Seattle in 2014, and even at the age of 35, shows no sign of slowing down. Instead of giving that terrible contract to Jacoby Ellsbury, they could have used that towards a bigger contract towards Robinson Cano. Cano was a star, and the perfect complement to Derek Jeter throughout his career. The Yankees didn’t want to pay the guy, even with how well he was playing. He was in the prime of his career, and maybe the Yankees thought they got the end of his prime. But he’s still going, and the Yankees have to look back on it and wish they did better.