Notable trades between Yankees & Red Sox

December 6th, 2023

The Red Sox and Yankees have spent more than a century trying to one-up each other while waging one of the fiercest rivalries in sports history, so it’s not exactly a surprise that they haven’t come together very often to trade, especially considering how that whole Babe Ruth deal (you might be familiar) turned out for Boston.

Just how rare is a swap between the two sides? Tuesday’s deal sending outfielder from Boston to New York in a four-player swap was just the eighth trade between the Yanks and Red Sox in the Divisional Era (since 1969).

Here’s a closer look at those trades and other notable transactions between the storied rivals.

Divisional Era (since 1969)

Red Sox get: RHP Greg Weissert, RHP Richard Fitts, RHP Nicholas Judice
Yankees get: OF Alex Verdugo

With one year remaining on his contract, Verdugo was shipped to New York for a trio of right-handed pitchers. Weissert pitched 31 1/3 innings with a 4.60 ERA for the Yankees before the deal, while Fitts was New York’s No. 12 prospect and Judice an eighth-round 2023 Draft pick. Verdugo, the key part of the trade sending Mookie Betts to the Dodgers in 2020, posted a .281/.338/.424 slash line across four seasons with the Red Sox.

Red Sox get: RHP Diego Hernández, cash
Yankees get: OF Greg Allen

Allen signed a Minor League contract with the Red Sox in January 2023 and was dealt to the Yankees four months later. The 30-year-old outfielder makes his return to the Bronx after appearing in 15 games for the Yankees in 2021. Allen, who spent his first four seasons with Cleveland and played in one game for the Padres in 2020, spent 2022 with the Pirates. He owns a career .232/.299/.336 batting line. Hernández made 12 appearances (five starts) for the Yankees' Rookie affiliate in 2022, pitching to a 2.10 ERA.

Red Sox get: RHP Frank German, RHP Adam Ottavino, cash
Yankees get: Player to be named later or cash considerations

With Ottavino heading into the final season of a three-year, $27 million deal and the Yankees looking to create more space under the $210 million competitive balance tax threshold in 2021, New York shipped the reliever to the Red Sox with German (the Yankees' No. 24 prospect) and some cash 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.

Red Sox get: INF Kelly Johnson
Yankees get: INF Stephen Drew, cash

The Red Sox and Yankees went more than 15 years without making a trade before this swap of veteran infielders prior to the 2014 non-waiver Trade Deadline. A month later, the Red Sox shipped Johnson to the Orioles in a four-player trade, which gave him the distinction of playing for all five American League East teams in a four-year span from '11-14. Drew was part of Boston’s World Series championship-winning club in '13, but after rejecting a qualifying offer from the Red Sox that offseason, he remained a free agent until re-signing with Boston in May '14, a little over two months before the Red Sox traded him to the Yankees.

Red Sox get: RHP Tony Armas Jr., RHP Jim Mecir
Yankees gets: INF Randy Brown, C Mike Stanley

Stanley had two stints spanning five seasons with the Yankees in the 1990s, but he wasn’t part of any of their three World Series teams during the decade, as he spent ’92-95 and part of ’97 in the Bronx, signing with the Red Sox after ’95 and the Blue Jays after ’97. 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.

Red Sox get: Cash
Yankees get: RHP Scott Bankhead

The Yankees purchased Bankhead from the Red Sox during the 1994 player strike. Bankhead re-signed with New York that offseason and went on to post a 6.00 ERA over 20 appearances (one start) during the 1995 campaign, his final season as a Major Leaguer.

Red Sox get: DH Don Baylor
Yankees get: DH Mike Easler

The Red Sox and Yankees swapped aging designated hitters shortly before Opening Day in 1986, with the 36-year-old Baylor going to Boston for the 35-year-old Easler. Baylor helped Boston win the AL East crown during his first season with the team, recording 31 homers with 94 RBIs over 160 games. He also hit .297 with a .909 OPS in the postseason as the Red Sox reached Game 7 of the World Series. Easler was productive for New York, meanwhile, hitting .302 with 14 homers and an .811 OPS over 146 games in '86. Both players were traded again the following season, Baylor to the eventual World Series champion Twins and Easler to the Phillies.

Red Sox get: 1B Danny Cater, INF Mario Guerrero
Yankees get: LHP Sparky Lyle

After posting a 2.85 ERA over 260 appearances for the Red Sox in his first five seasons, Lyle was sent to the Yankees in a three-player deal before the 1972 season. While Carter spent just three seasons with Boston and Guerrero two, Lyle continued to provide excellent relief work with his new club. The left-hander reached his pinnacle in '77, winning the AL Cy Young Award, and had a 2.41 ERA over seven seasons with the Yankees before being traded to a Rangers in a 10-player deal that brought Dave Righetti to New York.

Other notable trades

Red Sox get: C Elston Howard
Yankees get: RHP Ron Klimkowski, RHP Pete Magrini

After a legendary run with the Yankees in which he became the franchise’s first black player, earned 1963 AL MVP honors and won four World Series titles, Howard was traded to the Red Sox during the ’67 campaign. Boston ended up reaching the World Series, but Howard wasn’t able to secure his fifth ring, going 2-for-18 in Boston’s loss to the Cardinals. Howard returned to the Red Sox for one more season in '68, then called it a career.

Red Sox get: OF Cedric Durst, cash
Yankees get: RHP Red Ruffing

Ruffing’s career started inauspiciously, as he recorded a 4.61 ERA for the Red Sox over his first seven seasons, but he eventually found his groove after being traded to the Yankees in 1930. The right-hander ranks second in franchise history with 231 wins in the regular season and was a member of six World Series title winners, going 7-2 with a 2.63 ERA in 10 Fall Classic starts. Ruffing reached the Hall of Fame via a runoff election in '67, his final year on the ballot. Durst, meanwhile, didn't play in MLB after '30.

Red Sox get: INF Norm McMillan, RHP George Murray, OF Camp Skinner, cash
Yankees get: LHP Herb Pennock

After 10 unremarkable seasons with the Philadelphia Athletics and Red Sox, Pennock joined the Yankees and became a key member of a burgeoning contender. The left-hander helped the Yankees win the first World Series championship in franchise history during his first year with the team and won three more rings thereafter, going 5-0 with a 2.06 ERA in the Fall Classic for New York. Pennock was inducted into the Hall of Fame on his eighth ballot in 1948.

Red Sox get: 2B Del Pratt, C Muddy Ruel, LHP Hank Thormahlen, OF Sammy Vick
Yankees get: LHP Harry Harper, RHP Waite Hoyt, INF Mike McNally, C Wally Schang

Like Ruffing and Pennock, Hoyt built a Hall of Fame career after being traded from the Red Sox to the Yankees. The right-hander had a 3.48 ERA in the regular season and a 1.83 ERA in the World Series over 10 years with New York, winning three championships.

Red Sox get: Cash
Yankees get: P/OF Babe Ruth

In what might be the most famous sports transaction ever, the Yankees purchased Ruth from the Red Sox for $100,000 in a secret meeting the day after Christmas in 1919. What followed was decades of prosperity for the Yankees, while the Red Sox went 86 years without winning a World Series championship as the "Curse of the Bambino" took hold of Ruth's former franchise. The Sultan of Swat hit 659 homers in the regular season and another 15 in the World Series during his time with the Yankees, leading New York to four titles.