Every trade ever made between the New York Yankees and Boston Red Sox

With Alex Verdugo headed to the Bronx, let's look back at the rare deals between rivals

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Amidst slow winter meetings, two of baseball’s biggest rivals broke the ice by making a rare trade. The New York Yankees acquired Boston Red Sox outfielder Alex Verdugo in exchange for Richard Fitts, Greg Weissert, and Nicholas Judice.

According to MLB’s Sarah Langs, 2023 marks just the third calendar year in baseball history with multiple trades between the Red Sox and Yankees involving players on both sides, the first time since 1932.

In total, there have been seven trades between the Red Sox and Yankees since the divisional era began in 1969. There might be a reason for that. The two biggest rivals in all of sports probably don’t want to actually give themselves any real, meaningful talent. The swaps and cash considerations end up leading to short-term deals and one-off contracts. If anything, this will arm you with ample material for your next round of “Name Some Sports Guys.”

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2023

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2023

Alex Verdugo was meant to be the crown jewel return in the trade that sent Mookie Betts to the Los Angeles Dodgers. Verdugo spent four years with the Red Sox, and at points, looked like a solid hitter. But he never came close to justifying the trade for Betts. In exchange for the outfielder, the Yankees sent back three minor league pitchers: Richard Fitts, Greg Weissert, and Nicholas Judice. Only Weissert has made his major league debut, serving 29 games of relief over two years.

Earlier this year, the Bronx Bombers sent an outfielder — Greg Allen — to Beantown in exchange for minor leaguer Diego Hernandez.

Allen had already spent a few months in the Yankees system during 2021, sent there by the Padres in the James Reeves trade before being DFA’d that summer. Two years later, he found his way to their Triple-A team. New York, desperate for outfield help, acquired Allen for a minor league pitcher to replace Aaron Hicks in the lineup. Allen made it three weeks before suffering a right hip flexor strain. A month after recovering from the injury, the Yankees DFA’d him again.

In Allen’s combined two Yankee tenures, he made just 60 plate appearances and posted a .250 batting average, one home run, three RBIs, and eight stolen bases.

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2021

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2021

The New York Yankees traded Frank German and Adam Ottavino to the Boston Red Sox for a player to be named later.

German was the Yankees’ fourth-round pick in the 2018 MLB draft. Constantly hampered by shoulder issues, he was stuck on New York’s Class A team and hadn’t pitched a game since 2019. Adam Ottavino’s Yankee tenure is only notable in that he was the first Bronx Bomber in team history ever to be awarded the jersey number 0. The Red Sox, with a dearth of talent in their bullpen, acquired Ottavino for a player to be named. Ottavino played one season for the Red Sox, serving as one of their most effective bullpen arms despite posting a 4.21 ERA.

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2014

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2014

The Boston Red Sox traded Stephen Drew and cash to the New York Yankees for Kelly Johnson.

Drew was a major impact player for the Red Sox, homering in Game 6 of the World Series to help Boston secure the 2013 title. He turned down Boston’s initial $14.1 million offer the following offseason, but he ended up sitting on the open market until May because of a league-wide logjam at the position. Drew eventually signed a prorated version of the original qualifying offer before Boston and New York did an infielder swap. Drew would finish out the season in New York, then sign on again in 2015 for another year. In return, the Red Sox got infielder Kelly Johnson, who played 10 whole games for Boston before getting traded to Baltimore a month later. This made Johnson the first player to play for every AL East team since the MLB moved to six divisions in 1994.

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1997

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1997

The New York Yankees traded a player to be named later and Tony Armas to the Boston Red Sox for Randy Brown (minors) and catcher Mike Stanley. The New York Yankees sent Jim Mecir on Sept. 29, 1997, to complete the trade.

Stanley actually spent a ton of time bouncing around the Yankees and Red Sox over the course of his career, and nearly all his accomplishments happened with one of those teams. Stanley joined the Yankees in 1992. Over four years, the backstop secured his only Silver Slugger Award (1993) and All-Star nomination (1995). In 1996, he signed with the Red Sox in free agency, before going back to New York in this trade. Stanley signed with the Toronto Blue Jays in 1998, who traded him BACK to Boston the same year. Stanley hit a career-high 29 home runs in 1998, only seven of which were for Boston.

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1994

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1994

The New York Yankees purchased Scott Bankhead from the Boston Red Sox.

You know it’s a meaningful trade when photo repositories don’t have a picture of Scott Bankhead in uniform for either team. Bankhead was a relief pitcher who appeared in 67 games for the Red Sox over two seasons. He was purchased by the Yankees in September 1994 but never played for them because of the MLB strike. When free agency came around, Bankhead chose to re-sign with the Yankees, posting a 6.00 ERA in 20 games. The Yankees cut him in July of that year, marking the end of his major league career.

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1986

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1986

The New York Yankees traded Don Baylor to the Boston Red Sox for Mike Easler.

Don Baylor is a former MVP and a World Series champion, though neither accolade came while in Boston or New York. The vast majority of Baylor’s career success came with the then-California Angels. He eventually signed with the Yankees in 1983. He notoriously disliked his time in the Bronx, but he did secure two of his three career Silver Sluggers there.

Baylor made it three years into a four-year contract before trading him for Red Sox DH Mike Easler. In Boston, Baylor would make some crucial plays to push the Red Sox over the Angels in the 1986 ALCS. The Red Sox traded Baylor late in the 1987 season.

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1972

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1972

The Boston Red Sox traded Sparky Lyle to the New York Yankees for a player to be named later, and Danny Cater. The Yanks sent Mario Guerrero on June 30, 1972, to complete the trade.

Sparky Lyle: All-time name, all-time mustache. Lyle began his career with the Red Sox, where Ted Williams supposedly taught him how to throw a slider. He registered 64 saves over four years as the team’s closer, but things didn’t really heat up until he was moved to New York. There, Lyle became one of the best relief pitchers of the 1970s. He helped the Yankees win three straight AL pennants and two World Series titles, setting the American League record for saves (35) in 1972.

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Before 1969

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Before 1969

The New York Yankees purchased Babe Ruth from the Boston Red Sox.

Come on. Do we even have to mention this one? In one of the single-worst trades in sports history, the Red Sox traded one of the greatest hitters in the history of the sport so the Red Sox owner could finance a musical.