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Yankees Trade Partner History: Boston Red Sox

The list of transactions between the Yankees and Red Sox includes a number of players listed among the Bombers’ all-time greats.

Portrait of Red Ruffing and George Pipgras Photo by George Rinhart/Corbis via Getty Images

These days, a trade between the Yankees and Red Sox prompts shocked reactions not only from fans of both organizations, but from baseball fans in general. As the two biggest rivals in sports, these two teams have regularly gone long stretches of time without coming together on a deal, reaching 14-year droughts on two separate occasions (1972 to 1986, 1997 to 2014). The four trades made over the last decade, in fact, reflect the most active period in Yankees/Red Sox deals in over half a century, and none of those deals represent a blockbuster transaction (with this winter’s Alex Verdugo trade coming closest).

A long time ago in an American League far, far away, however, the Yankees and Red Sox were active trade partners. In the 1910s and 1920s, in fact, rarely did a year go by without the two organizations coming together on a deal. Fortunately for the Yankees, they tended to get the better of these deals on a fairly regular basis.

Best Trade

May 6, 1930. The Yankees trade Cedric Durst and $50,000 to the Red Sox for Red Ruffing.

I know what you’re thinking: “Wait a second, why isn’t this the Babe Ruth trade?” Technically speaking, the Yankees did not trade for Babe Ruth; they purchased his contract. In this series, we’ve tried to place an emphasis on actual trades rather than exchanges for pure cash, so with deep respect to the Great Bambino, we’re going to talk about someone else.

Deciding which pure trade qualifies as the best between the Yankees and Red Sox was a lot harder than it sounds. The two organizations made a series of deals in the years surrounding the Ruth purchase that brought Waite Hoyt (#47 in the Top 100 Yankees series), Herb Pennock (#49 in the series), Carl Mays, Sad Sam Jones, and more to the Bombers — basically, an entire pitching staff. In the 1970s, they acquired Sparky Lyle (#67 in the series), who would go on to be the first AL reliever to win a Cy Young.

In my book, though, the clear No. 1 option here is the 1930 trade for Red Ruffing, who will be profiled later today as #17 in the Top 100 series and was enshrined in Cooperstown. Durst put up a 65 OPS+ in 102 games for Boston and never played in the majors again.

Red Ruffing and Bill Dickey Talking Near Baseball Net
Ruffing and longtime batterymate Bill Dickey
Photo by George Rinhart/Corbis via Getty Images

Prior to coming to the Bronx, Ruffing was a JAG — Just Another Guy — with a career 4.54 ERA (94 ERA+) a 54-101 record. He led the league in losses twice. He was named the Opening Day starter in 1929 pretty much by default, as the Red Sox, then in the darkest days of their franchise history, had nothing else competent on the mound.

Desperate to raise some capital in fear of a foreclosure, the Red Sox sent their young pitcher to the Yankees in May 1930 in exchange for a backup outfielder, $50,000 in cash, and a $50,000 loan from Yankees owner Jacob Ruppert. At the time, the deal appeared insignificant, barely receiving a mention in the local newspapers. Yankees manager and former ace Bob Shawkey (#38 in the series), however, revamped Ruffing’s mechanics, and Ruffing went on to not only have a Hall of Fame career, but to become one of the greatest Yankee pitchers of all time.

Worst Trade

August 3, 1967. The Yankees trade Elston Howard to the Red Sox for a player to be named later and Pete Magrini. The Red Sox sent Ron Klimkowski (August 8, 1967) to the Yankees to complete the trade.

Let’s imagine, for a moment, that we’re dealing just with numbers, not with players. In this deal, the Yankees sent a backup catcher/pinch-hitter who slashed just .196/.247/.271 for the team in 1967 to the Red Sox in exchange for a pair of pitching prospects. Since the 1967 Yankees were in a race to the bottom of the American League, this looks like an absolute win for the Yankees.

Real life isn’t MLB: The Show or Out of the Park Baseball, however. The player involved in the deal was Yankees legend Elston Howard (#24 in our series). The trailblazer and 13-year veteran was heartbroken, and initially intended to refuse to go; eventually, influenced by his family, a phone call from the Red Sox owner, and the desire to win another World Series, he finally relented.

In many ways, the deal worked out for Howard. He helped the Red Sox reach the World Series in their “Impossible Dream” season, and was still able to return to the Bronx as a coach after his retirement. Even so, Howard should have retired a Yankee, not a member of the Red Sox — and that is why this deal goes down as the worst trade between the two organizations. (There weren’t many other contenders anyway.)

Most Overlooked Trade

July 29, 1919. The Yankees trade Bob McGraw, Allen Russell and $40,000 to the Red Sox for a player to be named later. The Red Sox sent Carl Mays (July 30, 1919) to the Yankees to complete the trade.

Some trades are overlooked because the players involved do not appear to be significant at the time of the transaction; the Yankees’ purchase of Gio Urshela, which went widely unreported, in 2018 comes to mind as the prime example in recent years. Other times, the baseball implications of the deal are immediately recognized, but years later, events force us to reinterpret the event in a new light.

From 1915 to 1919, Carl Mays was a dominant pitcher for the Boston Red Sox, but one who attracted controversy (it’d follow him to New York via the Ray Chapman tragedy as well). Everything came to a head in the middle of July in 1919, when he stormed off the mound after getting hit with an errant throw from his catcher. He soon went to the media and demanded a trade, saying, “I’m convinced that it will be impossible for me to preserve my confidence in myself as a ballplayer and stay with the Red Sox as the team is now handled.” For his actions, AL President Ban Johnson secretly suspended Mays for his comments and forbid American League teams from trading for him. Johnson was afraid that other players would follow in Mays’ footsteps, demand trades, and essentially destroy the reserve clause system that granted teams a monopoly on player movement.

The Yankees, White Sox, and Red Sox defied the order, and eventually the Yankees were able to swing a deal for his services. While Johnson tried to block the deal, these three teams were able to force him to back down. This represented Johnson’s first loss on a major issue and was, as Steve Steinberg puts it, “the beginning of the end of Ban Johnson’s iron rule over the league.”

American League Baseball
Ban Johnson
Photo by The Stanley Weston Archive/Getty Images

Weirdest Trade

July 31, 2014. The Red Sox trade Stephen Drew and cash to the Yankees for Kelly Johnson.

After the Yankees sent Jim Mecir and Tony Armas to the Red Sox in 1997 for old friend Mike Stanley, the two teams did not come together on a deal for 14 seasons. With the Yankees in need of a second baseman to replace the struggling Brian Roberts, they sent Kelly Johnson, a second baseman who the Yankees had played at first and third, to the Red Sox in exchange for Stephen Drew, a shortstop who the Yankees played at second base.

This deal was the definition of a lose/lose deal. Drew was absolutely horrible in pinstripes, slashing just .150/.219/.271. I still have no idea why they decided to bring him back for 2015, although he did do better that year. Johnson, somehow, was even worse, slashing .160/.160/.200 before being traded at the waiver deadline to the Baltimore Orioles, allowing Johnson to become the first player to play for all five AL East teams. If it wasn’t for the fact that everything around this deal was so strange — the drought, the position changes, the fact that both teams stunk — this would be an easy contender for “Worst Trade.” As it stands, it’s mostly just hilarious.

Other Transactions of Note

December 26, 1919. The Yankees purchase Babe Ruth from the Red Sox for $100,000.

Babe Ruth, Major League Baseball Player, Boston Red Sox, Portrait, National Photo Company, 1919 Photo by: Universal History Archive/Universal Images Group via Getty Images

I mean, it’s not a trade, but of course, it’s a “Transaction of Note” with a rich history. This Ruth fellow went on to a tiny bit of fame.

March 22, 1972. The Red Sox trade Sparky Lyle to the Yankees for a player to be named later and Danny Cater. The Yankees sent Mario Guerrero (June 30, 1972) to the Red Sox to complete the trade.

ALCS Game 4 - New York Yankees v Kansas City Royals

Sparky Lyle was one of the game’s best relievers with the Red Sox. With the Yankees, he was one of the game’s best pitchers, period. He would go on to win the 1977 AL Cy Young, as well as two World Series championships, in the Bronx. We already linked to Malachi’s excellent writeup of Lyle in the PSA Top 100 series, but we’ll do so again!

December 18, 1918. The Yankees trade Ray Caldwell, Frank Gilhooley, Slim Love, Roxy Walters, and $15,000 to the Red Sox for Dutch Leonard, Duffy Lewis, and Ernie Shore.

December 15, 1920. The Yankees trade Del Pratt, Muddy Ruel, Herb Thormahlen, and Sammy Vick to the Red Sox for Harry Harper, Waite Hoyt, Mike McNally, and Wally Schang.

December 20, 1921. The Yankees trade Rip Collins, Roger Peckinpaugh, Bill Piercy, Jack Quinn, and $100,000 to the Red Sox for Bullet Joe Bush, Sad Sam Jones, and Everett Scott.

January 3, 1923. The Yankees trade Al DeVormer and cash to the Red Sox for Harvey Hendrick and George Pipgras.

January 30, 1923. The Yankees trade Norm McMillan, George Murray, Camp Skinner, and $50,000 to the Red Sox for Herb Pennock.

Ed Barrow - New York Yankees
Ed Barrow was Yankees GM from 1920-45

Over the course of five seasons, BoSox manager-turned-Yankees GM Ed Barrow used his familiarity with the Boston organization to help the Yankees acquire a massive amount of arms from his old team, who dealt from what they perceived as a glut of starting pitchers. While considered mostly fair deals at the time, this came to be considered highway robbery by the Yankees, with Steve Steinberg arguing that the real reason the Yankees were able to overtake the Red Sox in the 1920s comes from the fact that Boston failed to replace all the veteran pitchers they sent southwards.


Anderson, R.J. “Yankees-Red Sox trades: Brief history of deals between rivals, from Great Bambino to Adam Ottavino.CBS Sports. January 25, 2021.


Corbett, Warren. “Red Ruffing.” Society for American Baseball Research. Accessed January 20, 2024.

Diemart, Joshua. “Pinstripe Alley Top 100 Yankees: #24 Elston Howard.” Pinstripe Alley. January 13, 2024.

Harrigan, Thomas. “Notable trades between Yankees & Red Sox.” December 5, 2023.

Ferenchick, Matt. “The most and least important Yankees/Red Sox trades in history.Pinstripe Alley. January 30, 2021.

Steinberg, Steve. “The Curse of the . . . Hurlers? Consequential Yankees–Red Sox Trades of Note.Society for American Baseball Research. Accessed January 20, 2024.

Tan, Celia. “Elston Howard.” Society for American Baseball Research. Accessed January 20, 2024.

Yankeeography, Volume 2: Elston Howard.

Previously in the Trade Partner History series

New York Mets
Full list to date