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The most and least important Yankees/Red Sox trades in history

From Babe Ruth to Stephen Drew, the Yankees and Red Sox have made some pretty big and truly pointless deals with each other over the years.

New York Yankees v Atlanta Braves Photo by Kevin C. Cox/Getty Images

The Yankees and Red Sox made a trade earlier this week, with Adam Ottavino and prospect Frank German going to Boston in exchange for a player to be named later or cash considerations.

It was the first deal the two rivals have made since 2014 and just the fourth in the last 35 years. They don’t do business with each other often. However at one point, they did, and did so a lot. From 1903 to 1948, the teams made 34 deals. From 1918 to January 1923, they made nine, several of which involved players going to the Yankees who then proved key to their first World Series titles. One of them was for Babe Ruth, which is still probably the most high profile trade in baseball history.

On the other hand, like there would be for any two teams’ trade histories, there’s also plenty of deals that affected nothing. The Ottavino swap is probably one of those. It involves the Yankees mainly just trying to shed salary. The Red Sox probably won’t be particularly good and will likely hope he bounces back in order to trade him at the deadline and get anything of value back. If the Yankees’ bullpen tanks and Ottavino puts in a solid season, it might come back to haunt them, but other than that scenario, this trade will probably be inconsequential.

While there are a couple exceptions, the vast majority of trades the teams have made with each other fall into those two categories: the extremely influential and the truly pointless. In the aftermath of the teams doing business again, let’s go back in history and look at the most an least important trades the Yankees and Red Sox have made.

3. Most Important: Herb Pennock to Yankees for Norm McMillan/George Murray/Camp Skinner/$50,000

Pennock was a disapointing Red Sox starter when the Yankees traded for him before the 1923 season. He then spent the next 11 seasons turning into arguably the final key piece of the first Yankees’ dynasty, putting up a career that would get him elected to the Hall of Fame.

As for the three they gave away, they played four combined seasons in Boston.

3. Least Important: Stephen Drew to Yankees for Kelly Johnson

The most recent deal prior to the Ottavino one is also one of the most pointless.

After Álex Rodríguez got suspended and Robinson Canó left for Seattle, the Yankees signed Kelly Johnson and Brian Roberts to help fill out the infield. Neither of those deals particularly worked, so they flipped Johnson for 2013 World Series winner Drew and released Roberts shortly after. Drew was somehow worse, putting up a 39 OPS+. Incredibly, that was enough for the Yankees to bring him back in 2015.

2. Most Important: Red Ruffing to Yankees for Cedric Durst/$50,000

As the rotation, including Pennock, that helped to their first four championships started to get old, the Yankees went back to the old well of wayward, but potential-filled Red Sox starters.

After debuting as a 19-year-old in 1924, Ruffing had become the de facto ace of a downtrodden Boston franchise. He was their best pitcher, but that was more because the team was bad than Ruffing being good. In his best years, he had been little more than league average.

The Yankees traded utility man Durst for him in 1930. Durst would never play again after that season. As for Ruffing, he won six World Series titles and is a Hall of Famer.

2. Least Important: Mike McNally to Red Sox for Howie Shanks

In December 1920, the Yankees got McNally as part of an important Red Sox trade: the one that got them Waite Hoyte. Four years later after some mostly substandard hitting, they flipped him back to Boston for someone named Howie Shanks. It was a flip of one below average utility man for another.

Shanks played 66 games for the Yankees and put up a 68 OPS+. McNally played no games in his second stint in Boston, as they traded him to the Senators the day after acquiring him.

1. Most Important: Babe Ruth to Yankees for $100,000

Big shocker, I know. The most important trade between the two is also probably the biggest in the history of the sport. With it, the Yankees went from middling team into the biggest and most popular franchise in the sport. Ruth won a ton, pretty much rewrote the record books, and became a baseball legend and icon.

The Red Sox, meanwhile, didn’t win another World Series until 2004 — allegedly, I still don’t remember that season actually ending — but according to legend their owner did get some money to fund a Broadway musical, although it’s unclear if that’s true.

If this trade doesn’t happen, maybe the Red Sox became the biggest dynasty in baseball history with Ruth leading the way. Maybe instead of New York, Boston sends him somewhere else and that team has the Yankees’ history. Maybe the Yankees become plucky underdogs with a long World Series drought. It might’ve changed everything. On the other hand, here’s one that changed nothing.

1. Least Important: Billy Gardner to Red Sox for Tom Umphlett

Billy Gardner was a backup on the 1961 Yankees after they acquired him from the Twins in June of that year. The 33-year-old veteran helped the Yankees to a World Series, although I use “help” loosely. He had a 57 OPS+ in 41 regular season games and then had one at-bat in the Fall Classic. The next June, after he had only played in four games, the Yankees sent him to Boston.

In return, they got back 31-year old outfielder Umphlett. So, uh, fun fact about Umphlett: he played his last major league game in 1955. You may have noticed that is before the trade that brought him to the Yankees. It’s seven years before. He came up with the Red Sox back in 1953, was traded to the Senators after that season, was traded back to Boston ahead of the ‘56 season, spent seven seasons in their minor league system, was traded to the Yankees, played two seasons with them, and then spent four seasons in the Twins’ system. I’m not sure there’s any more pointless trade in history than acquiring a guy seven years after what would be his final MLB game.