A History of Trades Between the New York Yankees and Boston Red Sox

Yankees/Red sox Trades

It’s fairly rare to see trades between teams within the same division; it’s even more rare to see a trade between bitter division rivals. The New York Yankees and the Boston Red Sox have one of the most storied rivalries in sports history. The two rivals have spent over a century trying to one-up each other and have only engaged in eight trades since the divisional era (1969). Why would they do business? The reasons can vary, but all fans can agree that seeing a transaction between the two teams is “unusual.”

Divisional Era (1969-Present)


Yankees get: OF Alex Verdugo

Red Sox get: RHP Greg Weissert, RHP Richard Fitts, RHP Nicholas Judice

Photo by Terrance Williams/AP

In the most recent trade between the two rivals, the Red Sox sent Alex Verdugo to the Yankees with one year left on his contract for three right-handed pitchers. The Yankees were in dire need of an everyday left-fielder, and with hot-prospect Jasson Dominguez requiring Tommy John surgery in September of 2023, they needed to make a splash during the offseason. Verdugo is remembered as a key part of the trade that brought Mookie Betts to the Dodgers in 2020. Verdugo also recently earned some headlines as a representative of Team Mexico during the World Baseball Classic. He slashed .281/.338/.424 across four seasons with the Red Sox. Weissert was the only former Yankee included in this trade that had played in the majors, pitching 31 1/3 innings with a 4.60 ERA for the Yankees before the deal. Fitts was New York’s No. 12 prospect, and Judice was an eighth-round 2023 Draft pick.


Yankees get: OF Greg Allen

Red Sox get: RHP Diego Hernández cash

The 30-year-old Allen signed a Minor League deal with the Red Sox in January of 2023 and was traded to the Yankees four months later. Allen was in familiar territory as he had appeared in 15 games for the Yankees during the 2021 season. Allen is known as a serviceable outfielder with a fast set of wheels but suffered a right hip flexor strain in June of 2023. Before his injury, he owned a slash line of .214/.313/.571. He was later DFA’d by the Yankees. Hernández made 12 appearances (five starts) for the Yankees’ Rookie affiliate in 2022, pitching to a 2.10 ERA.


Yankees get: Player to be named later, or cash considerations

Red Sox get: RHP Frank German, RHP Adam Ottavino, cash

Photo by Michael Starghill/MLB Photos via Getty Images

The leading name in this trade was Ottavino, who was approaching the final season of a three-year, $27 million deal. The Yankees were looking to create more space under the $210 million competitive balance tax (CBT) threshold in 2021, so they shipped the reliever to the Red Sox with German (the Yankees’ No. 24 prospect) and some cash over to cover part of Ottavino’s contract. Ottavino posted a 4.21 ERA in 62 innings for the Red Sox in 2021 before signing with the Mets. Ottavino is currently a free agent.


Yankees get: INF Stephen Drew & cash

Red Sox get: INF Kelly Johnson

Drew was a member of Boston’s World Series championship-winning team in 2013. Still, after rejecting a qualifying offer from the Red Sox in the offseason, he remained a free agent until re-signing with Boston in May of 2014; two-months later, he was sent to the Yankees. Kelly Johnson only spent a short time with the Red Sox before being sent to the Orioles, earning the distinction of playing for all five American League East teams in four years from 2011 to 2014.


Yankees get: INF Randy Brown, C Mike Stanley

Red Sox get: RHP Tony Armas Jr., RHP Jim Mecir

Photo by Focus on Sport/Getty Images

Mike Stanley spent 1992-1995 and part of 1997 with the Yankees, avoiding being a part of their three World Series-winning teams in the 1990s. Four months after this trade, the Red Sox sent Armas to the Expos as the player to be named to complete their deal for Pedro Martinez.


Yankees get: RHP Scott Bankhead

Red Sox get: Cash

The Yankees purchased Bankhead from the Red Sox during the 1994 player strike, which resulted in the only World Series not to be played since 1904. Bankhead re-signed with the Yankees and pitched a 6.00 ERA over 20 appearances during the 1995 season, his last season as a major leaguer.


Yankees get: DH Mike Easler

Red Sox get: DH Don Baylor

The Yankees and Red Sox swapped veteran designated hitters shortly before opening day in 1986. Baylor helped Boston win the AL East pennant during his first season with the team, recording 31 homers with 94 RBIs over 160 games. He also performed well during the postseason, batting .297 with a .909 OPS as the Red Sox reached Game 7 of the World Series. Easler performed well in New York during his first season in the Bronx, batting .302 with 14 home runs and an .811 OPS over 146 games. Both players would be traded again the following season, with Baylor moving to the eventual World Series champion Twins and Easler to the Phillies.


Yankees get: LHP Sparky Lyle

Red Sox get: 1B Danny Cater, INF Mario Guerrero

Photo by Focus on Sport/Getty Images

Lyle posted a 2.85 ERA over 260 appearances for the Red Sox in his first five seasons but was traded to the Yankees in a three-player deal before the 1972 season. Cater spent just three seasons with Boston and Guerrero two; meanwhile, Lyle provided excellent relief work with the Yankees. The left-hander won the 1977 Cy Young Awards, pitching a 2.41 ERA over seven seasons with the Yankees before being traded to the Rangers in a deal that brought David Righetti to New York.

Pre-Divisional Era


Yankees get: RHP Ron Klimkowski, RHP Pete Magrini

Red Sox get: C Elston Howard

Howard was a former MVP and the Yankees first black player before he was traded to the Red Sox during the 1967 season. During his first year in Boston, he reached the World Series with the goal of securing his fifth ring but came up short, going 2-18 in Boston’s loss to the Cardinals. He played one more season with the Red Sox before announcing his retirement.


Yankees get: RHP Red Ruffing

Red Sox get: OF Cedric Durst cash

Photo by National Baseball Hall of Fame

The Red Sox traded an “average” pitcher to the Yankees in 1930, but he became a household name once he entered his new clubhouse. Ruffing ranks second in franchise history with 231 wins in the regular season and was a member of six World Series-winning teams. He went 7-2 with a 2.63 ERA in 10 World Series starts. Ruffing was inducted into the Hall of Fame in 1967. Meanwhile, Durst didn’t play in the MLB again after 1930.


Yankees get: LHP Herb Pennock

Red Sox get: INF Norm McMillan, RHP George Murray, OF Camp Skinner, cash

Herb Pennock was seen as unremarkable during his first ten seasons with the Philadelphia Athletics and Boston Red Sox. Once he was traded to the Yankees in 1923, he became a key member of the franchise’s first World Series championship-winning team and won three more rings with the Yankees afterward. Pitching to a 5-0 record in the Fall Classic and an exceptional 2.06 ERA, Pennock was inducted into the Hall of Fame on his eighth ballot in 1948.


Yankees get: LHP Harry Harper, RHP Waite Hoyt, INF Mike McNally, C Wally Schang

Red Sox get: 2B Del Pratt, C Muddy Ruel, LHP Hank Thormahlen, OF Sammy Vick

Like Ruffing and Pennock, Hoyt built a Hall of Fame career after being traded from the Red Sox to the Yankees. During his ten seasons with New York, he pitched a 3.48 ERA in the regular season and a 1.83 ERA in the World Series. He was a member of three World Series championship-winning teams in the Bronx.


Yankees get: P/OF Babe Ruth

Red Sox get: Cash

This is what began the “Curse of the Bambino.” The Yankees purchased Ruth from the Red Sox for $100,000 in a secret meeting the day after Christmas in 1919. It would be 86 years before the Red Sox would win a World Series championship in 2004. Before this trade, Ruth had played a pivotal role in winning three World Series championships for the Red Sox, who at the time had won more titles than any other team (5 of 15), including the first World Series played in 1903. As a member of the Yankees, The Great Bambino hit 659 home runs in the regular season and another 15 in the World Series. Ruth would lead the Yankees to four titles while setting the groundwork for what would become the most successful sports franchise in American History: the New York Yankees.

Jacob P.M.

Covering the New York Yankees - Find me on X/Twitter: @JacobBSpeaks

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