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On Monday, the New York Yankees sent a pair of right-handed pitchers (Adam Ottavino and Frank German) to the Boston Red Sox in a move designed to net one side a few interesting arms while helping the other create financial flexibility. The Yankees now can, and presumably will, bring back veteran outfielder Brett Gardner without exceeding the luxury-tax threshold and exposing themselves to overage penalties. 

The Ottavino trade was intriguing for reasons other than the immediate implications for both sides. It represented the second trade between the Yankees and Red Sox since Major League Baseball expanded to 30 teams in 1998, and the first between the AL East rivals since 2014. 

Join with us now, dear reader, as we detach from the troubling present to seek comfort in the past, for it's due time to provide a brief history of notable trades between the Yankees and the Red Sox. (Note: a full transactions log between the franchises can be found at 

July 31, 2014

Prior to Monday's swap, the two sides last agreed on a move back at the 2014 trade deadline. That's when the Yankees sent Kelly Johnson to Boston in exchange for Stephen Drew. It proved to be a nothingburger of a trade, with Johnson appearing in 10 games with the Red Sox and Drew stumbling to a 39 OPS+ the rest of the way.

Still, it was remarkable within its own right because it was the first time in more than 15 years the two sides had agreed to do business. Indeed, before that fateful July day, the Yankees and Red Sox had not traded with one another since 1997.

Aug. 13, 1997

What happened in 1997 that made the two sides treat each other as persona non grata in trade talks? Probably not what you'd expect.

The Yankees dealt Tony Armas Jr. and Jim Mecir for Mike Stanley and Randy Brown. Stanley performed well for the Yankees, and they made the postseason as a wild card before losing to Cleveland. Alas, owner George Steinbrenner was reportedly displeased that the Red Sox were soon thereafter able to spin off Armas to the Montreal Expos to net a pitcher named Pedro Martinez.

Martinez, of course, would subsequently ignite a longstanding rivalry with the Yankees. Steinbrenner, evidently, never forgot that the Yankees had played a (minor) part of the deal by trading Armas to the Red Sox in the first place.

March 28, 1986

It should be noted that the two sides had experienced droughts well before the Stanley trade was ever made. In 1986, the Yankees and Red Sox swapped Don Baylor and Mike Easler, a trade that the Yankees came out ahead on, albeit slightly. 

Anyway, the real point of introducing that trade is to point out that the Baylor-Easler trade was the first between the clubs in 14 years -- or since the Yankees fleeced the Red Sox for reliever Sparky Lyle.

Prior to the Lyle trade, the two sides had reliably made trades within at least five years of each other dating back to the 1940s. And, before then, they were constantly swapping parts, including one trade that you've undoubtedly heard a lot about.

Dec. 26, 1919

Yup, this is the big one. The Yankees purchased Babe Ruth from the Red Sox in exchange for $100,000. No one reading this needs a history lesson on how poorly this trade worked out for the Red Sox, but it is worth clearing up one misconception: the belief that Boston owner Harry Frazee used the money solely to finance a play called "No, No, Nanette." That play, quite successful, didn't become a reality until 1925.

Whatever the motivation, the two sides didn't stop dealing as Ruth ascended in pinstripes. During the 15-year period Ruth spent in New York, the Yankees and Red Sox agreed to an additional 14 trades. Clearly there were no hard feelings.