Yankees Players Who Became Red Sox: The Ultimate Betrayal

In this blog post, we’ll take a look at some of the most notable Yankees players who decided to don the Red Sox uniform later in their careers.

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Yankees-Red Sox Rivalry

It’s the biggest rivalry in baseball. Yankees vs. Red Sox. It’s a war. Fans bleed pinstripes or red, diehard loyalty handed down from generation to generation. For some, the rivalry is bigger than the game. It’s a way of life. So what happens when a Yankee breaks the cardinal rule and dons the hated rival’s uniform? Betrayal.

Origins of the rivalry

The Yankees–Red Sox rivalry is a Major League Baseball (MLB) rivalry between the New York Yankees and Boston Red Sox. The two teams have competed in MLB’s American League (AL) for over 100 years and have since developed one of the fiercest rivalries in all of professional sports.

Notable players who have played for both teams

One of the most iconic and well-known rivalries in all of sports is the one between the New York Yankees and the Boston Red Sox. The two teams have been battling it out for American League supremacy for over a century now, and the competition between them is as intense as ever. Ironically, some of the best players in baseball history have donned both jerseys at some point in their careers. Here are some of the most notable examples.

Babe Ruth is arguably the greatest baseball player of all time, and he is certainly one of the most influential figures in Yankee history. He spent the first six years of his career with Boston, winning three World Series titles with them. In 1918, he was sold to New York for $125,000, a then-record amount for a player transfer. Ruth would go on to have an illustrious career with the Yankees, setting numerous batting records and helping them win seven World Series titles. His departure from Boston is still considered one of the most controversial trades in baseball history, and his success with New York only added to the intensity of the rivalry between these two teams.

Another player who made headlines by switching allegiances from Boston to New York was outfielder Reggie Jackson. Jackson was already a superstar when he joined the Yankees in 1977, but he cemented his legacy by hitting three home runs in Game 6 of the World Series that year. He helped lead New York to victory over their hated rivals that year, enraging Red Sox fans everywhere. Jackson would go on to play five more seasons with the Yankees, winning two more World Series titles before retiring in 1981.

There have been many other big names who have played for both sides in this rivalry over the years, including Roger Clemens, Wade Boggs, Jason Varitek, and Johnny Damon. While some players have had success with both teams, others have not been so lucky. Regardless of how they fared on the field after changing uniforms, all of these players will always be remembered for betraying one fan base or another in this storied rivalry.


The Yankees and Red Sox rivalry is one of the oldest and most heated rivalries in baseball. So when a player from one team goes to the other, it is seen as a betrayal. Here are some of the most notable players who have betrayed the Yankees by going to the Red Sox.

What it means to be a Yankee

The New York Yankees are one of the most iconic and revered sports franchises in history. They have won 27 world championships, more than any other MLB team, and their storied rivalry with the Boston Red Sox is the stuff of legend. But despite all their success, the Yankees have had their fair share of traitors over the years. Here are some of the most notable players who betrayed the Bronx Bombers by donning the red and white of their hated rivals, the Red Sox.

Babe Ruth
Arguably the greatest player in baseball history, Babe Ruth started his career with the Red Sox and helped them win three World Series titles. But in 1920, he was sold to the Yankees in a move that would come to haunt Boston for generations. Ruth went on to has a legendary career with New York, setting numerous batting records and winning four more World Series titles. His legacy as a Yankee is so strong that many fans forget he even played for Boston.

Mike Mussina
A five-time All-Star during his 18-year MLB career, Mike Mussina spent 10 seasons with the Yankees, winning nine Gold Glove Awards and finishing in the top six of Cy Young voting five times. He was one of the best pitchers in Yankees history and helped them win six AL East titles and one World Series championship. But after 2001, Mussina decided to sign with the Red Sox as a free agent, spending his final eight seasons in Boston. He was an integral part of their 2004 title team and even won another Gold Glove Award with them in 2008.

Reggie Jackson
Reggie Jackson is one of only two players to have won World Series titles with three different teams (the other is Lou Piniella). He famously helped lead the Yankees to back-to-back championships in 1977 and 1978, hitting five homers in those two Fall Classics combined. But after helping New York win yet another AL pennant in 1981, Jackson became a free agent and decided to sign with… you guessed it…the Red Sox! Jackson only spent one season in Boston before being traded back to the Yankees midway through 1982. He would finish his Hall of Fame career where it started – in pinstripes – retiring after 1986 season.

Johnny Damon
After spending four years with the Red Sox (2002-2005), Johnny Damon helped them break their 86-year championship drought by playing a key role on their 2004 title team. He became a fan favorite in Boston for his all-out style of play and long flowing locks, but he made enemies for life when he decided to sign with archrival New York prior to 2006 season. Damon would spend four years as aYankee, winning another World Series title in 2009 before being let go via free agency following 2010 campaign. He would go on to play for several other teams before retiring from baseball altogether after 2014 season

Why players switch teams

In recent decades, there have been several high-profile cases of MLB players leaving their team via free agency to sign with a hated rival. These so-called “traitors” are often met with anger and betrayal by the fans of their former team. While some players switch teams simply for the money, others do it for a chance to win a championship. In any case, these 10 players all made the ultimate betrayal by joining the Boston Red Sox.

1. Johnny Damon
Johnny Damon was a key member of the 2004 Red Sox team that broke the “Curse of the Bambino” and won Boston’s first World Series in 86 years. He then left the Sox to join their arch-rivals, the New York Yankees, in 2006. While he helped the Yankees win a World Series in 2009, he was roundly booed whenever he returned to Fenway Park.

2. Wade Boggs
Wade Boggs is one of the greatest hitters in Red Sox history. He won five batting titles and was elected to the Hall of Fame in 2005. However, he became a free agent after the 1992 season and controversially signed with the Yankees. He won another World Series with New York in 1996 and was once again booed when he returned to Fenway Park.

3. Curt Schilling
Curt Schilling was another key member of the 2004 Red Sox team that broke the “Curse of the Bambino.” He played a pivotal role in Boston’s comeback victory over their rivals,the New York Yankees,in Game 6 of the American League Championship Series that year. However, he became a free agent after the 2007 season and surprisingly signed with…the Yankees! He only made 11 starts for New York before retiring, but his betrayal is still remembered by Red Sox fans to this day.

4. Jacoby Ellsbury
Jacoby Ellsbury was drafted by the Red Sox in 2005 and made his major league debut with Boston in 2007. He quickly emerged as one of baseball’s top young stars, winning two Gold Glove Awards and being named to two All-Star teams during his seven seasons with the team. However, Ellsbury became a free agent after 2013 and shocked everyone by signing a seven-year contract worth $153 million with…the Yankees! He has since won two more Gold Glove Awards and been named an All-Star once more while playing in New York.

“DeflateGate” refers to a controversy involving allegations that the New England Patriots deliberately underinflated footballs used during the 2014 AFC Championship Game against the Indianapolis Colts (which they won 45-7). The Patriots were subsequently fined $1 million and lost two draft picks as punishment for their actions. But many people believe that Patriots quarterback Tom Brady knew about or even instructed his team’s equipment staff to deflate footballs below league regulation levels. This possible betrayal by one of Boston’s most iconic athletes has divided fans across New England ever since.”


The New York Yankees and the Boston Red Sox have been rivals for over a hundred years. So, when a player decides to switch from the Yankees to the Red Sox, it is seen as a betrayal. The fans, the media, and even the players react to this switch with disbelief and anger. Here are some of the most famous cases of Yankees players becoming Red Sox.

How Yankees fans react to players who switch teams

Yankees fans are some of the most passionate and die-hard fans in all of baseball. They live and breathe their team, and they expect the same level of commitment from the players. So, when a player who has been drafted and developed by the Yankees goes to another team – particularly the Red Sox – it is seen as a huge betrayal.

The reaction from Yankees fans can be quite intense. Some fans will stop following the player entirely, while others will boo them mercilessly whenever they come back to play at Yankee Stadium. Some fans might even go so far as to burn jerseys or other memorabilia associated with the player.

In general, Yankees fans view players who leave for the Red Sox as traitors and enemy combatants. It is one of the most fierce rivalries in all of sports, and there is no love lost between these two fan bases.

How Red Sox fans react to players who switch teams

There are few things that can enrage a Red Sox fan quite like seeing one of their favorite players don a Yankees uniform. It’s the ultimate betrayal, and it’s something that most fans never forget (or forgive).

It’s hard to say exactly why this is such a big deal, but part of it has to do with the rivalry between the two teams. The Yankees are the Evil Empire, and anyone who aligns themselves with them is immediately seen as the enemy. There’s also the fact that the Red Sox have a history of losing, so any time a player leaves for greener pastures, it feels like another punch to the gut.

So, how do Red Sox fans react when one of their own defect to the enemy? Here are a few examples:

-They boo them mercilessly whenever they come back to Fenway Park.
-They make sure to let them know that they are no longer welcome in Boston.
-They try to forget that they ever existed.
-They plot ways to get revenge on them (usually by rooting for them to fail).


The New York Yankees and the Boston Red Sox are two of the most iconic and storied franchises in all of professional sports. The two teams have been bitter rivals for over 100 years, and the rivalry is only intensified when a player decides to leave one team and join the other. In this article, we will take a look at some of the most high-profile examples of players who have made the ultimate betrayal and gone from the Yankees to the Red Sox.

How players who switch teams impact the Yankees-Red Sox rivalry

The Yankees-Red Sox rivalry is one of the most well-known and intense in all of sports. There is no love lost between these two teams, and it often seems like players who switch teams are viewed as traitors by the fans.

While it’s true that some players have had a significant impact on the rivalry, others have not. Here is a look at some of the more notable players who have switched teams in recent years:

1. Johnny Damon: Damon was one of the key members of the “Idiots” Red Sox team that broke the Curse of the Bambino in 2004. He then joined the Yankees in 2006 and helped them win a World Series. He was not well-liked by Red Sox fans when he made the switch, but he endeared himself to Yankees fans with his play on the field.

2. Robinson Cano: Cano was a homegrown Yankee who became one of their best players. He then left to join the Seattle Mariners in 2014, sign a massive contract. While he has not had much success with his new team, he is still disliked by many Yankees fans.

3. Wade Boggs: Boggs was another member of those infamous “Idiots” Red Sox team, but he left following the 1992 season to join the Yankees. He won a World Series with them in 1996 and was inducted into the Hall of Fame as a Yankee in 2005. He is still revered by Red Sox fans, but not so much by Yankees fans.

4. David Cone: Cone started his career with the Mets, but he will always be remembered for his time with the Yankees. He was a key member of their 1990’s dynasty, winning four World Series titles with them. He then returned to the Mets in 2003 and won another World Series with them that year. He is currently working as a television analyst for both teams, so he has managed to stay neutral in the rivalry!

How the Yankees-Red Sox rivalry impacts baseball

The Yankees-Red Sox rivalry is one of the most storied and intense in all of baseball. It began in the early 1900s when the Yankees, then known as the New York Highlanders, emerged as a powerhouse team. The Sox, meanwhile, were mired in a long championship drought dating back to 1918.

The two teams have since met in countless thrilling moments, from Bucky Dent’s ’78 home run to Aaron Boone’s walk-off homer in 2003. On the field, there’s no love lost between these two bitter rivals.

But what happens when a player switches sides? That’s the ultimate betrayal.

It’s happened dozens of times over the years, with varying degrees of success. Some players, like Babe Ruth and Roger Clemens, go on to find great success with their new team. Others, like Adrian Gonzalez and Jacoby Ellsbury, are never able to live up to expectations.

But no matter how a player fares after switching allegiances, one thing is certain: it always makes for a fascinating story.

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