Love them or hate them, the New York Yankees have the greatest legacy out of any baseball team in the league. With their astounding 27 World Series titles, there will never be a team that will ever catch them. However, with this being the case, there is absolutely no question that playing for the Yankees adds on an entirely different level of pressure. The pinstripes hold a significant amount of power. It is every baseball player's dream, unless they are from Massachusetts, to one day have the chance to play there. However, this amount of pressure has led to a lot of even the best players in the league to struggle once joining them. Some players can handle it and do well, while others just completely fall off.
With all that has been stated thus far, we will be looking at ten recent Yankees who struggled with the team and ten who thrived. A lot of the names on this list will be very recognizable, as they have been able to have fairly solid careers at a minimum. However, there is sometimes no way to thrive with an organization that puts an immense amount of pressure on its players. It is what makes playing with the Yankees so difficult, They expect greatness and rightfully so with their history. However, some players just have been able to grow their careers to be even stronger when playing there and become fan favorites in the process. It truly is impossible to tell which way it will go once a new player signs there.
Now, let’s take a look at these Yankees!
20 Struggled: Sonny Gray
Although Sonny Gray is technically still a member of the New York Yankees, the team has made it clear that they are going to trade him this offseason. This is a move that will end up being best for both parties because it is clear that he has not been a good fit for the organization.
Gray was supposed to be a top of the rotation pitcher for the team, but this simply never became the case. This past season was particularly poor, as it saw him put up a 4.90 ERA on a winning team. For a pitcher with the expectations to be an ace, this definitely is underwhelming.
19 Thrived: J.A. Happ
J.A. Happ was acquired by the Yankees at the trade deadline. He was having himself a very solid season with the rebuilding Blue Jays, so the trade was understandable. However, no one would have predicted that Happ would go 7-0 and have a very solid 2.69 ERA with the team.
The Yankees are going to have to work hard to re-sign Happ because he had a spectacular season with them. However, with him expecting to hit the open market, there is a pretty strong chance that he is heading elsewhere. Regardless of what occurs, he absolutely thrived as a rental for the team.
18 Struggled: Chase Headley
Chase Headley was expected to be a top-notch acquisition for the Yankees. The team gave him a four-year, $52 million contract when he signed back in 2014, but he would never live up to it. His numbers fell off dramatically as soon as he put on the pinstripes and his career essentially ended.
The Yankees would end up trading him back to where his career started with the San Diego Padres. This season would end up being disappointing for him and it is now extremely unlikely that he will ever play in the league again. The Bronx was just a bad career decision for the veteran.
17 Thrived: Starlin Castro
Starlin Castro was the main piece that the Yankees gave up in the Giancarlo Stanton trade. Although the Yankees got a star in Stanton, it is important to note that Castro was very good with the Yankees as well. In fact, he even was an All-Star with the team back in 2017.
There is no question that Castro ended up being a solid fit for the team during his time there. Although the team decided to move on from him, it is absolutely clear that he did his job quite well. He definitely is a player that the team could look to bring back some day if possible.
16 Struggled: Billy Butler
By the time that Billy Butler joined the Yankees, his career was in jeopardy. The veteran power hitter simply saw his numbers drop off dramatically. The Yankees decided to give the former all-star a chance to thrive with them, but it ultimately did not occur in the slightest.
Butler was not very effective coming off the bench and simply appeared to be a waste of a roster space. Butler simply did not provide the same effectiveness as he did during his 29-home run season with the Royals back in 2012. At the end of the day, he just could not find his groove in New York.
15 Thrived: Nathan Eovaldi
Nathan Eovaldi was one of the many heroes of the Boston Red Sox World Series team this year. There is no question that he is in line for a pretty huge contract when he hits the open market. However, it is important to note that he actually had a pretty solid amount of success with the Yankees too.
In his 2015 season with the team, Eovaldi put up a very respectable 14-3 record and was one of their best pitchers. However, after the following season, the team decided to move on from him and he ends up being injured for 2017. Signing with the Rays and then being traded to the rival Red Sox helped him out immensely.
14 Struggled: Neil Walker
The Yankees were looking to add some pop to their lineup for this season and signed Neil Walker. This looked like a wise move at first because of the fact that he had a pretty successful season the year before. Consistency has always been one of his strengths, but it disappeared with the Yankees.
This season was a complete failure for the veteran and he saw all of his offensive statistics drop off completely. With this, it is definitely clear that the Walker signing was not a good one for the Yankees. He will likely look to go elsewhere now, as he is set to become a free agent again.
13 Thrived: Alex Rodriguez
Alex Rodriguez is one of the most controversial baseball players in the history of the league, but there is no denying that he was a superstar. Rodriguez had a significant impact on the Yankees and put up some of his best major league seasons with the team. With that, it is clear he thrived.
Rodriguez had a spectacular postseason with the team back in 2009 and managed to win a plethora of individuals awards with the club as well. When Rodriguez would officially retire in 2016, he had 351 career home runs with the team, as well as over 1,000 RBIs.
12 Struggled: Matt Holliday
When Matt Holliday was in his prime, he was definitely one of the most underrated stars in the entire league. A lot of this had to do with the fact that he was playing with the Colorado Rockies and was not getting a lot of recognition. However, that would change once he was on the Cardinals, where he played some of his best baseball ever.
In 2017, Holliday would end up signing with the Yankees and they envisioned him to be their DH. However, it became quite clear that he could not handle the pressure of playing in New York much at all, as his stats would show. After batting just .231 that year with limited power numbers, the team moved on from him.
11 Thrived: Todd Frazier
The New York Yankees shocked the MLB world when they were contenders during the 2017 season. They were in the midst of a rebuilding period, but their young stars blossomed far quicker than they predicted. With that, the team were sellers at the deadline and picked up power hitter Todd Frazier.
Frazier would end up being a solid acquisition for the team because of his leadership skills. He definitely had a decent amount of power for the team as well, as he hit 11 home runs in just 66 games for them. His tenure with the team resulted in him getting a solid contract from the Mets that offseason.
10 Struggled: Brian McCann
The Yankees signed Brian McCann to a five-year, $85 million contract back in 2014. At that point in time, McCann was one of the best catchers in the entire league and frequently was an all-star due to that. However, once he joined the Yankees, his career went completely south.
Now, that is not to say that McCann was bad in New York, but it is clear that he dropped in skill immensely. He essentially lost his ability to hit for contact and he no longer was viewed as an elite player. The team would end up trading him to the Houston Astros after the 2016 season because of this.
9 Thrived: Zach Britton
The Yankees took a bit of a gamble on trading for Zach Britton this trade deadline because of all the injury problems he had. He struggled this season with the Orioles, but the Yankees wanted to take a chance on him because of his past success. This would end up being the right move for them.
Although the Yankees did not win the World Series this year, Britton did provide them with some solid relief pitching. It is clear that the change in scenery did wonders for him and now he has more value as a free agent this offseason. At the end of the day, this was a positive move for both parties.
8 Struggled: Stephen Drew
Stephen Drew came into a tough position with the Yankees because he was the first shortstop after Derek Jeter’s retirement. That amount of pressure could have very well led to his significant drop in statistics with the team in 2015. However, it is unacceptable when seeing how much he struggled.
With the Yankees that season, Drew ended up batting .201 and it made the team quickly give up on him. There is no question that Drew simply did not fit into the system of the team well and his inability to hit for contact destroyed his overall value. He would never be the same from there and was out of the league entirely at the end of the 2017 season.
7 Thrived: Mark Teixeira
Mark Teixeira was a spectacular signing by the baseball club because he played a huge role in their World Series win back in 2009. It appears that he was able to develop his game entirely with the Yankees and soon became known as one of the top power hitters in all of baseball.
There is no question that Teixeira was already an elite player before joining the Yankees, but he got even better there. Although his ability to hit for contact fell off at the end of his career, all in all, this signing was a successful one for the team. He should be heavily respected for all of his contributions.
6 Struggled: Andrew McCutchen
The Yankees knew that they needed some help with their outfield if they wanted to be champions this season. The Red Sox and Astros were just too much for them to handle at that point, so they decided to trade for Andrew McCutchen. This looked like a solid move for the contending team.
Yet, McCutchen just could not find his game in New York and ended up being a complete bust for the pinstripes. He would only end up batting .133 in the postseason, which of course, was a complete letdown. At the end of the day, he simply was not a good fit for the team and will not be brought back.
5 Thrived: Carlos Beltran
Carlos Beltran was definitely a very smart addition for the Yankees, as his leadership was greatly appreciated. Even with his old age, Beltran was able to have some of the best seasons of his career in New York. It is a shame that he was not able to play for them when they were at the top though.
At the end of the day, the Yankees got far more than they expected from Beltran. This is evidenced especially by the fact that he was an All-Star in 2016 for them. However, they would end up trading him to the Texas Rangers from there because they were out of playoff contention.
4 Struggled: Lance Lynn
Lance Lynn was lights out for the St. Louis Cardinals during the beginning stages of his career. However, this season was one that he struggled with immensely. After starting the season with the Twins, the Yankees decided to give him a chance there and acquired him for their postseason run.
The Yankees had hoped that Lynn could find the dominance he had just the season before, but it just was not meant to be. Lynn just was unreliable and his statistics got even worse. His awful postseason with the Yankees will also ensure that he will not be back with the team next season.
3 Thrived: Andrew Miller
Andrew Miller was a spectacular piece of the Yankees during his tenure there. It was in New York where he was able to develop into the All-Star that he is today. He was their closer for one season, but they then switched him to a set-up role where he was able to thrive even more.
At the end of the day, there is a good chance that Miller would have still been with the team if they did not struggle so badly in 2016. However, even with his tenure being short, he was a great piece of the team and a player who definitely could even find his way back there in the future.
2 Struggled: Jacoby Ellsbury
There is a very little chance that the Yankees are going to be playing Jacoby Ellsbury ever again. The veteran missed all of last season and just has been a big disappointment for them since signing his massive seven-year contract back in 2014. He was never the same after leaving the Red Sox.
If Ellsbury somehow ends up playing again, there is no chance that he will ever be the player that he once was. The Yankees made a massive mistake with this signing and when reviewing his statistics, it is one that actually could have been avoidable. He had not been the same player since his 2011 all-star season with Boston.
1 Thrived: C.C. Sabathia
C.C. Sabathia’s tenure may come to an end this offseason, as he is a free agent. The team has noted that they are looking to bring in a new core of players with this year’s class being so strong. Perhaps they could sign Sabathia again, as he does deserve a new contract, but we will see.
However, if this is the end of Sabathia’s tenure and even career, one must respect all he has done in New York. His first handful of years with the team were absolutely dominant. Although he hit a rough patch for three seasons, he has been able to regroup and ended up being a top-notch pitcher again. At the end of the day, there is no 2009 World Series without Sabathia.