The most memorable players who played for both Red Sox and Yankees

How many players in MLB history have played for both the Boston Red Sox and New York Yankees?

When the New York Yankees acquired former Boston Red Sox star Andrew Benintendi from the Kansas City Royals ahead of the trade deadline, he became the 236th player in MLB history to play for both teams in baseball’s biggest rivalry.

On Friday, Benintendi will return to Boston for the first time since the Sox traded him to the Royals.

Ahead of the three-game series between the two scuffling rivals, take a look back at some of the most memorable players who wore both uniforms:

Charlie Hemphill

Charlie Hemphill was the first Red Sox player to also play for the Yankees. He joined the Sox for their inaugural season in 1901 and played 136 games for them that year.

Unfortunately, Hemphill arrived in Boston with a less-than-stellar reputation; the Boston Globe called him “the poorest outfielder in the league.” After a brief stint in Cleveland and five years with the St. Louis Browns (now the Baltimore Orioles), Hemphill finished out his career playing four seasons with the Yankees. In 1912, he transitioned into the role of player-manager in the minor leagues, but when he got drunk and didn’t report for a game, he was fired and his contract was sold to another team.

Jack Chesbro

Jack Chesbro was one of the great pitchers of the early 1900s, twice leading the league in games started. In 1904, his MLB-leading 55 games pitched included 48 complete games and a grand total of 454 2/3 innings. It would’ve been a guaranteed Cy Young Award season, but the award wouldn’t exist for another half-century; Young himself was pitching for the Red Sox at the time.

Unlike most of the players on this list who left Boston for New York, Chesbro went from the Yankees to the Sox in 1909. The future Hall of Famer made exactly one start for the Red Sox before retiring.

Duffy Lewis

The year before Babe Ruth’s trade broke the pre-internet baseball world, Duffy Lewis (whose first name was also George), got traded from the Sox to the Yanks after missing the 1918 season while serving in the Navy during the first World War.

Lewis played for the Sox from 1910-17 along with fellow outfield stars Harry Hooper and Tris speaker, and when Fenway Park opened in 1912, his defensive prowess on the incline in front of the Green Monster became known as Duffy’s Cliff. He’d help the Sox win three rings before the trade.

Ironically, Lewis was the only player to ever pinch-hit for the Bambino.

Babe Ruth

Ever heard of him?

George Herman Ruth, also known as Babe, The Bambino, The Sultan of Swat, the Colossus of Clout, etc. will forever be known as the linchpin of the rivalry. While the rivalry between the two cities long predates and is about so much more than baseball, the sale of Ruth’s contract from Beantown to the Bronx was a defining moment; the ripple effect continued for almost a century.

After six seasons with the Sox between 1914-19, during which the Sox won their third, fourth, and fifth rings, Boston’s musically-minded owner, Harry Frazee, sent Ruth to New York for $100,000 and a $350,000 loan that mortgaged Fenway Park.

The trade turned the tables more dramatically than anyone could have foreseen. Ruth, who’d begun to transition from pitching to full-time slugging, went on to set most of baseball’s offensive records. The Yankees, who had never won a World Series in their short franchise history, began their likely-eternal tenure as the winningest team in MLB history. Their 27 championships, including four with Ruth, are more than double the total won by any other team. The Sox, who’d been one of the most successful American League teams since winning the first-ever World Series in 1903, wouldn’t win another until 2004. The championship drought became known as The Curse of the Bambino, and Yankees fans were known for chanting “1918! 1918!” to taunt Sox fans. Fittingly, they mounted a historic comeback against the Yankees to break it, and have been the more successful team in this millennium, winning four championships (04, 07, 13, 18) to the Yankees’ one (2009).

Elston Howard

Eight years after Jackie Robinson broke MLB’s color barrier, the Yankees made catcher Elston Howard their first Black player in 1955.  By 1963, he was the first Black player to win the American League MVP, and by the time the Yankees traded him to the Sox in 1967, he had 12 All-Star Games, four World Series rings and two Gold Glove awards under his belt.

Upon the Sox releasing him in October 1968, Howard returned to the Bronx as the first Black coach in the AL, and worked on two more championship teams.

Jackie Jensen

Jackie Jensen’s 170 home runs with the Red Sox are the most by a player who also played for the Yankees. He spent the 1950-52 seasons in the Bronx but was far more successful once he shipped up to Boston in 1954.

George Scott

Before Wade Boggs stepped on the scene, George Scott was the longest-tenured Red Sox player to also play for the Yankees. After 1,192 games with the Sox from 1966-79, the eight-time Gold Glove-winner played 44 games for the Royals and 16 games for the Yankees in the final season of his career.

Luis Tiant

Should-be Hall of Famer Luis Tiant was one of the first Red Sox players to depart for the Yankees in free agency in 1978. After Curt Flood fought for his right to not be a Philadelphia Phillie in 1969, Catfish Hunter, Dave McNally, and Andy Messersmith became the first true free agents in 1974-75.

A few years later, the collapse of the reserve clause and the new world of free agency meant that Tiant could

However, in retirement, El Tiante returned home to Boston, where he remains a beloved part of the fabric of Fenway. His Cuban sandwich shop is a fixture on Jersey Street, and fans will often find him sitting there, ready to chat and sign autographs.

In other words, after sampling both teams, he chose the better one.

Don Baylor

Don Baylor is one of the rare players to be part of a trade between the two rivals.

After three years in the Bronx, they dealt him to the Sox in 1986. He won Silver Slugger awards with both teams, and after the Sox lost in heartbreaking fashion in the 86 Fall Classic, they traded him to the Minnesota Twins the following summer, and with them, he got a ring.

Wade Boggs

Of all the players on this list, no one spent more time in a Sox uniform than Wade Boggs, who played 1,625 games for Boston between 1982-92. The following year, he departed for the Bronx, where he played the 1993-97 campaigns, finally winning a World Series.

While Boggs’ best offensive years were clearly during his Boston tenure, when he won six Silver Slugger awards in nine seasons, he won his only two Gold Gloves with the Yankees.

Jose Canseco

Jose Canseco was far more memorable in the early years of his career in Oakland and for being one of the faces of steroids in baseball, but he did spend the 1995-96 seasons slugging 52 homers in Boston and played 37 games for the Yankees in 2000.

Rickey Henderson

Hall of Famer Rickey Henderson spent most of his 25-year career with the Oakland A’s, 14 years in four stints, to be precise. But in between, he spent 596 games for the Yankees and 72 games for the Sox.

Roger Clemens

Roger Clemens’ incredible career began with 13 seasons in Boston, during which time he won three Cy Young awards. When he hit free agency ahead of the 1997 season, the Sox didn’t make him a good enough offer (sound familiar?), so he signed with the Blue Jays instead.

Clemens won two more Cy Young awards with Toronto, and then another one once they traded him to the Yankees ahead of the 1999 season. It was in New York that he finally got his two World Series rings, too.

David Cone

David Cone adopted Tiant’s pitching style and played on the Yankees with Clemens. After also being traded from the Blue Jays to the Yankees during the 1995 season, Cone established himself as a dominant pitcher on some of the Yankees’ late-90s championship teams, adding four more World Series rings to his fingers to go with his 1992 bling.

When he reached free agency, the Sox signed the 1994 Cy Young-winner for the 2001 season. He’s now a color commentator for Yankees games and does Sunday Night Baseball broadcasts on ESPN.

Mark Bellhorn

Mark Bellhorn’s midseason switch from the Sox to the Yankees in 2005 was basically the beginning of the end of his career. After helping make history in 2004 with several clutch postseason hits, he struggled so much the following year that the Sox actually released him. He signed with the Yankees soon after, but only appeared in nine games. After a season with the Padres and a few more major and minor-league stints, he officially retired in 2009.

Johnny Damon

For Sox fans growing up in the early 2000s, Johnny Damon’s departure was one of the first great betrayals of our lives. Barely a year after he’d cemented himself as one of the heroes of the 2004 team, he chopped off his flowing Jesus hairdo and signed a four-year, $52M contract with the Evil Empire.

It certainly stung to see Damon in pinstripes. He’s also one of the only players on this list to win a World Series with each time.

Doug Mientkiewicz

Doug Mientkiewicz’s time in Boston was brief, but memorable. For starters, he was acquired in the historic Nomar Garciappara midseason trade. Then, he participated in the greatest comeback in sports history, and became part of the iconic 2004 championship.

After single-season stints with the Mets and Royals, Mientkiewicz spent the 2007 campaign in pinstripes. Unfortunately, it didn’t work out too well for him, as the Sox won the World Series again that year.

Kevin Youkilis

The Greek God of Walks spent the first nine years of his ten-year career in Boston. He was a rookie when they won it all in 2004, and was instrumental to their repeat in 2007, when he won his only Gold Glove award. In the following two seasons, he hit 27+ home runs each year and went to his first two All-Star Games, a feat he’d repeat one last time in 2011.

Unfortunately, when the Sox were going nowhere in 2012, they dealt him to the Chicago White Sox.

Like Mientkiewicz, Youk’s season in the Bronx coincided with a Sox championship; after playing in pinstripes in 2013, he retired. And like Tiant, Youk returned to the Sox in his retirement years. He’s now an analyst on NESN.

Mike Lowell

Mike Lowell actually made his MLB debut with the Yankees in 1998, but only played eight games for them. Nevertheless, he received his first World Series ring that year, before getting traded to the Florida Marlins in February 1999.

After a cancer scare, he proceeded to have an excellent tenure in Miami, including winning a World Series in 2003, before being traded with Josh Beckett and Guillermo Mota to the Red Sox after the 2005 season. In retrospect, it’s funny that Lowell was the contract the Marlins wanted to unload, as he went on to be excellent in Boston, leading them to their second championship in four years. He became just the second Puerto Rican player ever to be named World Series MVP, following in Roberto Clemente’s footsteps.

Jacoby Ellsbury

Jacoby Ellsbury replaced Johnny Damon as the traitor of the century when he departed for the Bronx on a seven-year, $153M contract barely a month after helping the Sox win their third championship in ten years. And unlike Damon, who supposedly tried to stay in Boston, Ellsbury was keen to depart, making him all the more villainous to Red Sox Nation.

However, it ended up working out quite well for Boston, as injuries derailed Ellsbury’s career. By 2018, he wasn’t playing, and by the end of 2019, the Yankees released him. They still owed him $26M for the 2020 season and his buyout for 2021, and attempted to get out of paying it on the basis that Ellsbury had received unauthorized medical treatments.

His contract is now considered one of the worst in Yankees history.