There is no question that both the Yankees and Red Sox are two of the biggest franchises in the history of the MLB. Although the Yankees have dominated them for much of their history with their 27 World Series titles, the Red Sox have started this century off with a bang by already having four championships during it. The rivalry is also back at its highest point yet again, as both teams chirped each other immensely during the postseason this year. It is clear that they have a lot of players who fit perfectly on their rosters, which is why they are succeeding. However, even with this being the case, it is essential to recognize that this is not always the case. In fact, many players of late have been complete busts for the teams.
With all that has been stated thus far, in this article, we will be looking at ten recent players for both the Yankees and Red Sox who flopped. Many players simply do not succeed in these massive markets because of the fact that there is an abundance of pressure when playing for them. As previously stated, these teams have very rich histories that not many teams can match in the slightest. With that being stated, it is always essential for these players to play well for these teams. Yet, it sadly sometimes is not the case. At the end of the day, many of the players on this list will be very recognizable, as they had a lot of success elsewhere. However, they just could not muster up that skill with these iconic teams.
Nonetheless, let’s look at these players who flopped!
20 Boston: Drew Pomeranz
When the Red Sox acquired Drew Pomeranz from the San Diego Padres, he was having a career year. He made his first All-Star team and his future looked very bright. He would end up having another very solid season with the Red Sox in 2017 and he was seen as another top notch started for them.
However, this season with the team was absolutely awful for him, and now his future in Boston appears to be over. With a 2-6 record with a 6.08 ERA, it would be best for him to move on from the team. He does have the potential to turn it around, but it is clear that playing in Boston hurt him.
19 New York: Lance Lynn
Lance Lynn had an abundance of success in the MLB with the St. Louis Cardinals. Although he struggled this season with the Twins in his first season there, the Yankees picked him up as a rental. Lynn struggled even more in New York and now his career could be in jeopardy.
Lynn’s fate in New York came to a complete end after his abysmal postseason with the team. There is no question that it would be better for both parties to move on from one another. Perhaps Lynn could find success in the league again if he goes back to the National League.
18 Boston: Hanley Ramirez
Hanley Ramirez was expected to be a top notch signing for the Red Sox. He was definitely an elite player during his prime years in the MLB and deserves a plethora of respect because of it. However, it is fair to state that his time in Boston was not the best.
The Red Sox designated Ramirez for assignment this season because they felt that he was not worth the money for next year’s bonus. This was the right move for the team because his statistics had fallen off a bit. Although he could be serviceable again, it is clear that he was not a star in Boston.
17 New York: Andrew McCutchen
Looking to bolster their offense for the upcoming postseason, the Yankees made a deal with the Giants for Andrew McCutchen at the trade deadline. This looked like a smart move because although his stats had dropped a little, he was still a reliable player.
However, it became clear pretty quickly that McCutchen simply did not fit well with the Yankees and his production suffered. He struggled immensely playing under the pressure in New York, and as a result of this, will definitely not be back for the upcoming season. It is pretty clear that this is for the best for everyone involved.
16 Boston: Aaron Hill
To gear up for their 2016 postseason run, the Red Sox decided to trade for Aaron Hill. This seemed like a wise move because Hill had been having a very solid season with the Milwaukee Brewers. With him being a veteran as well, he seemed like he could be another leader for the Sox.
However, his successful season would soon turn the wrong way entirely one he joined Boston. He would only bat .218 and no longer had the ability to hit for contact. At the end of the day, Hill is another player who simply could not handle the pressure of playing in Boston.
15 New York: Chase Headley
The Yankees needed another hot bat in their lineup, so they went on to trade for Chase Headley in 2014. After this, he was given a four-year extension and seemed to be in their long-term plans. However, all of his ability to be clutch completely went away from there.
Headley had a lot of success with the Padres because they were a smaller market. However, playing in New York was not a good part of his career and he would never end up being the same. At this point in time, it is likely that Headley will never again play in the MLB.
14 Boston: Carson Smith
Carson Smith is a rarity on this list because his time in Boston was not necessarily bad. However, this season would end up being extremely disappointing because he would go on to injure himself in a very illogical way. He threw his glove out of frustration and torn his labrum.
Needless to say, Smith will not be back with the Red Sox ever again after this showing. There is a chance that he may never be the same pitcher as well because that is a serious injury. At the end of the day, Smith essentially threw away his own tenure with the Red Sox.
13 New York: Matt Holliday
Matt Holliday had an amazing MLB career and deserves a plethora of respect for all that he accomplished. His time with the Colorado Rockies and St. Louis Cardinals were nothing short of spectacular and he will go down as one of the most underrated stars of this generation.
However, it is important to note that Holliday did not have much success during his short tenure with the Yankees as their DH. He would only bat .231 with the team and did not have much pop in his bat as well. At the end of the day, Holliday is another player who simply could not play in New York.
12 Boston: Jake Peavy
During his prime years in the MLB, Jake Peavy was an absolute star with the San Diego Padres. Many people envisioned him becoming one of the best pitchers of all-time for a short while, but that would soon change after his tenure in San Diego would come to a close.
The Red Sox would end up trading for him in 2013 to help with their World Series chances. He would do fairly well his first season with the team, but completely dropped off in his second and last year. He would have a 1-9 record with a 4.72 ERA, which would result in him being dealt to the Giants.
11 New York: Neil Walker
The Yankees were looking to add another reliable bat to their lineup last offseason and brought in Neil Walker as a result. Walker had a very solid tenure with the Mets and it seemed that he would be a player who could handle the pressure of playing in the Bronx.
However, this would not be the case, as Walker would go on to have his worst season ever in the MLB. He saw his batting average drop to .219 and he only hit 11 home runs in the process. This was just a very down year for the veteran and he will look to regroup next season with a new team.
10 Boston: Justin Masterson
Once a top prospect for the Red Sox in the late 2000s, Justin Masterson found himself back with the team in 2015. He had a very solid tenure with the Cleveland Indians, so it seemed likely that he would go on to have success in Boston. However, this would not be the case in the slightest.
Masterson would go on to pitch only one season with the team. Although he sported a 4-2 record, his ERA was 5.61 and he lost his spot in the rotation. At the end of the day, this season would end up being the last one of his career because he was incredibly unreliable.
9 New York: Brian McCann
Brian McCann was an absolute All-Star during his time with the Braves and was considered to be the best catcher in all of baseball. Due to this fact, the Yankees would go on to sign him to a monster five-year deal back in 2014. However, he would start to drop off immensely there.
McCann was never a star in New York like he was in Atlanta. This would result in the team trading him before the final year of his contract to the Astros. There is no question that he was a solid player with the Yankees, but he was nowhere near the player he once was during his prime.
8 Boston: Allen Craig
Allen Craig was the main piece in the John Lackey deal with the St. Louis Cardinals and already was an All-Star in 2013. It looked like Craig would become a huge part of the Red Sox moving forward, but he completely dropped in skill in all areas once he made it to Boston.
In his short tenure with the team, he would not even reach the Mendoza line in both of his seasons. This would result in Craig being sent down to the minors in 2015. He would never end up making the team again and now is viewed as one of the biggest busts to ever play for the Sox.
7 New York: Jacoby Ellsbury
Although Jacoby Ellsbury is technically still under contract with the Yankees, there is a very good chance that he will never play for the team again. He missed the entirety of this season and never has been able to be the same player that he once was with the Red Sox.
After signing a massive seven-year contract with the Yankees, Ellsbury was supposed to be a top notch player for the team. However, even when he was healthy, he lost his starting spot and was a bench player. When seeing how much money he is making, it is clear that this was a complete disappointment.
6 Boston: Rusney Castillo
The Red Sox signed the biggest international free agent of 2014 when they locked up Rusney Castillo to a seven-year, $72.5 million deal. The team saw him as a future core piece, but as one can guess, this did not happen in the slightest. In fact, he is now seen as one of the biggest busts.
Castillo has not played in the MLB since 2016 and there is a very good chance that he will never make the roster in Boston again. When seeing that he is still under contract until 2021, this is easily one of the biggest wastes of money in the history of the MLB. He just did not produce as advertised.
5 New York: Chris Capuano
Chris Capuano had a very solid MLB career during his prime years with the Milwaukee Brewers, but everything took a turn for the worst when he joined the Yankees. He would only go on to play for two seasons with them, but it would essentially mark the end of his career.
Capuano struggled immensely in New York and this is evidenced when looking at his statistics. His worst season came in 2015 with them when he went 0-4 in the bullpen, while carrying a 7.97 ERA. This would be the end of his time in New York and it would easily be the worst point of his career.
4 Boston: Pablo Sandoval
After being an integral part of the San Francisco Giants and winning three World Series with them, Pablo Sandoval was got a massive contract with the Red Sox before the 2015 season. This was viewed as an amazing move because the veteran had so much success beforehand.
However, his time in Boston was easily one of the worst tenures in the history of the organization. He would end up dropping in average each season with the team and virtually had no power. His work ethic was questioned as well and the team finally designated him for assignment in 2017.
3 New York: Ichiro Suzuki
There is no question that Ichiro Suzuki is one of the best baseball players in the history of the MLB. However, as soon as he joined the Yankees, his statistics dropped off dramatically and he was never the same player. One can blame age, but it is clear that he did not live up to the expectations handed to him.
Suzuki was supposed to be the team’s leadoff hitter and be a real star for them. However, this would not be the case and he would never end up hitting over .300 with the team again. For a player who hit as high at .372 with the Mariners, this definitely was a disappointment for fans.
2 Boston: Ian Kinsler
The Red Sox needed a second baseman with the injury to Dustin Pedroia this season. Due to this fact, the team traded for Ian Kinsler at the trade deadline. This definitely was a move that was met with praise because Kinsler had a very solid career and has had a lot of postseason experience.
However, this trade simply would not work out at all for the team. Kinsler did not hit very well for contact and just seemed to be a shell of his former self. However, the worst moment was when Kinsler threw away Game 3, literally, with an egregious error. If he made the simple play, the Sox would have swept the Dodgers.
1 New York: Chris Carter
The Yankees were looking for a power bat for the 2017 season, so they landed a big free agent in Chris Carter. Carter had just come off a fantastic season with the Brewers that saw him hit 41 home runs. This seemed like a very smart move for the team, as he looked like the perfect DH.
However, his time in New York was very short lived because his power numbers dropped off completely and he only was hitting .201 by the time the team released him. With only 8 home runs in 62 games for the team, it became clear that he just was an awful fit and a very big disappointment.