Players moving between the Red Sox and the Yankees has been as common and frequent as the express air shuttle between the two cities.

Of the 251 players who played for both teams, here’s some of the most significant switches. Which team has come out ahead?

2024: The Cuban Missile Soars!

Signing Aroldis Chapman as a free agent is one of the more prescient moves by the Sox. A closer who has won two World Series and having played 7 seasons with the Yankees, at the age of 37, Aroldis Chapman is on the verge of setting the Red Sox record for the lowest ERA for a reliever. With a history of acquiring closers, Boston has secured Chapman's services for 2026 and will have an option for 2027 as well.

2024: A starting catcher as last

Carlos Narváez was traded for Elmer Rodriguez-Cruz in December, 2024 and has become the Red Sox starting catcher has played stellar defense and has also hit 11 home runs through August 24, 2025, while Elmer Rodriguez-Cruz has rapidly ascended from A to AA in the minor leagues with stellar performance.

Stats for Elmer Rodriguez-Cruz from Baseball-reference.com through August 26, 2025

2024: Alex Verdugo cut loose three years in a row

Signed for 5 years, Alex Verdugo was traded to the Yankees after year 4 for 3 players:  Nicholas Judice, Richard Fitts and Greg Weissert.  Despite getting to the 2024 World Series with the Yankees, Verdugo was again allowed to leave as a free agent, signed a minor league deal with the Atlanta Braves, was called up in April, but released in July, 2005. Will his trifecta of new teams be the end or will a fourth team take a chance on him?

2013: 7 phat years followed by 7 lean ones

7 productive years with the Red Sox and two World Championships for Jacoby Ellsbury attracted the Yankees who outbid the Red Sox with a 7-year contract with an 8th year option. However, Jacoby's production was leaner during his Yankee years and saw Jacoby released before his contract was up.

2006: The Caveman shaves

After 4 years and 1 World Series win, Johnny Damon heads to New York, shaves his beard to abide by the Yankees’ grooming code, and plays for four more years and one more championship, missing one other Red Sox championship during that time.

1996: The Rocket lifts off

After 192 wins, 3 20+ win seasons, and 3 Cy Young Awards, Roger Clemens left as a free agent in 1996 as Boston management believed he was in the "twilight" of his career. Signing with Toronto, Clemens won the Cy Young award in back-to-back seasons before being traded to Yankees.

Two World Series championships, another 20-game winning season, three other World Series appearances, one with his hometown Astros, and two more Cy Young awards, 7 total, the most all-time, rounded out Clemens' career. 

1996: Mike Stanton fortifies the pen

After 1.5 seasons with the Red Sox, Mike Stanton was traded to the Rangers and then signed with the Yankees starting a streak of 6 years in the post season and 3 World Series championships. A 19-year career showed that a talented lefthander is always in demand.

1993: Chicken Dinners in New York

A 5-time AL batting champ with the Red Sox, Wade Boggs had a .369 career average in Fenway, the highest all-time, but after his 1^st sub-.300 season in 1992, Wade Boggs was not re-signed and entered free agency. Boggs left Boston and joined the Yankees, winning two World Series, and then played his final two seasons in Tampa Bay, collecting his 3,000th hit. Wade Boggs was elected to the Hall of Fame in 2005.

1986: The Hit Man for the Groove

Don Baylor, a former MVP, was traded for Mike Easler in an exchange of designated hitters. In exchange for future Cy Young award winner John Tudor, Easler came over from the Pittsburgh Pirates and hit .313 with 27 home runs and 91 RBIs in 1984, but his production dropped the following year. As a right-handed batter, Baylor was better suited for Fenway Park and hit 31 home runs, bringing heart of the order offense and clubhouse leadership that contributed to Boston's winning the AL pennant in 1986.

1978: El Tiante goes out

Luis Tiant won 122 games and was a 20+ game winner 3 times for the Sox but was only offered a 1-year contract after the 1978 season. Instead, he took a two-year deal with the Yankees and a 10-year post-playing deal as a Yankee scout, leaving as a free agent. A viable Hall of Fame candidate, Luis was on the BBWAA ballot for 20 years and was on 6 Veteran Committee ballots but never achieved that honor before passing away at 83 in 2024.

1977: The Bear can’t get over the mountain in Fenway

Hoping to reverse the trend of giving players to the Yankees, the Red Sox signed Mike Torrez as a free agent who was fresh off a World Series win with the Yankees after the 1977 season. It almost paid off as Torrez led the Red Sox to a tie at the end of the 1978 season and started the tie-breaking 163^rd game. Leading 2-0 with two outs in the 7^th inning, Torrez served up a 3-run homer to Bucky Dent, giving the Yankees a lead they would not relinquish. Winning 60 games for the Red Sox over 5 years, Torrez’s first year, 1978, was the only year the Red Sox came close to the post-season.

1972: “Why pitch 9 inning when you can get just as famous pitching 2?”  Sparky Lyle

Debuting in 1967, Sparky Lyle missed the World Series due to a sore arm. He emerged as the Red Sox closer in those first 5 MLB seasons. Before the start of the 1972 season, Sparky Lyle was traded for 1^st baseman Danny Cater and shortstop Mario Guerrero. Arriving in New York, he became their closer and was the first reliever to win the Cy Young Award in 1977 and that year was the first of back-to-back world championships for him and the Yankees.

1930: Red Yankee

Red Ruffing was traded for a backup outfielder in 1930 and $50,000. Although he lost 20 games twice for the Red Sox, he won 20+ games 4 times in a row for the Yankees winning 6 World Championships and 7 pennants. Red Ruffing was elected to the Hall of Fame in 1967.

1921: Waite Hoyt from Schoolboy to Aristocrat

Starting his professional career at the age of 15, Waite Hoyt joined Boston for his major league debut. After his first two major league seasons in Boston, Waite Hoyt was traded in an 8-player deal in 1921 to the Yankees, where he led them to 6 pennants and two world championships.  A popular broadcaster after his playing days, Waite Hoyte won 237 games, all but 10 of them with Boston and was inducted into the Baseball Hall of Fame in 1969 by the Veteran’s Committee.

1919: The Bambino for Nannette

The most well-known player move was Babe Ruth. After 6 years in Boston and 3 World Championships, the Bambino was sold after the season in 1919 to the Yankees for $100,000 to help fund the first stage production of the play that would become the musical No No Nanette. This sale allegedly started the curse of the Bambino which resulted in the Red Sox never winning the World Championship again for 86 years.

1919: Mays to the Yankees

After two back-to-back seasons where he won more than 20 games (22 and 21) and pitching on two World Series champions in 1916 and 1918, Carl Mays was shipped mid-season in 1919 from the Red Sox to the Yankees for $40,000 and two other players. Carl Mays went on to win 26 and 27 games for the Yankees and helped take them to two more World Series. Carl Mays is infamous for throwing the pitch that killed batter Ray Chapman in 1920, the only major league player killed during a game.

So who do you think has done better, the Sox or the Yankees in exchanging players over the years?