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Some of the most intriguing Red Sox-turned-Yankees of baseball history

With Andrew Benintendi wearing the pinstripes for the first time, what other former Red Sox players toured with the Yankees?


Many believed the Red Sox struck gold when they selected Andrew Benintendi 7th overall in the 2015 MLB Draft. This was an outfielder that stood out immediately in high school, hitting an absurd .564 with more RBI’s than games played (12 HR, 57 RBI, 38 SB). His success continued at Arkansas, hitting .380 his junior season en route to the Dick Howser trophy in 2015 before venturing off to the big leagues.


Now, sure enough, 7 years later, Benintendi has a solid MLB resume. He won a World Series with Boston in 2018, a Gold Glove in 2021, and a nod to the All Star Game in 2022 as a Kansas City Royal. It was enough to tempt the Yankees, in dire need of a reliable third outfielder, to trade three prospects for Benintendi this week.


Yes, his ring with the Red Sox is for the cross-region rival. Yes, he’s got a beard. Yes, it’s a rental - his $8.5 million contract expires at the end of the year.


And yes, this has happened before.


Let’s look at some of the most intriguing players who have suited up for both the Yankees and the Red Sox over the years, and who won each swap.


Note: this is definitely not an exclusive list, and maybe we can even dive into more players who made the swap, too…there are a lot of them.


Babe Ruth

Winner: Yankees

The most obvious of the bunch, Ruth had his contract purchased by the Yanks for $100k. His 29 home runs led the league at the time (a bonkers statistic). People forget that Ruth was both pitching and hitting before it was cool - the Shohei Ohtani of generations past, if you will. This one has a clear winner - the Yankees won 4 Fall Classics with Ruth, while the Red Sox didn’t win a single one until 2004.


Wade Boggs

Winner: Tie

You can certainly make the claim that Wade Boggs, the generation’s best contact hitter, was a better asset to the Red Sox if he hadn’t been a crucial part of the Yankees’ success in the 1990’s. Boggs’ worst year with the Sox was one that he hit .302…if you forget that “down” year, it was a .325 campaign in his third year in the MLB. Boggs and Tony Gwynn hit over .350 in four straight seasons, something a duo hadn’t done since 1931. When he slumped to under .260 in ‘92, the Sox let him walk, and the Yankees came knocking. Who can forget Game 4 of the 1996 World Series? Boggs came off the bench to pinch-hit in a game that the Yankees rallied back from 6-0, worked the count full and drew a bases-loaded walk to put the Yanks ahead, and rode off on the NYPD horse despite a crippling fear of horses. Yes, Boggs may have had his best years with the Red Sox, but without him, the Yankees might not have come out on top in 1996 to start their era of dominance in the next few years.

Jacoby Ellsbury

Winner: Red Sox

I remember exactly where I was when the Yankees signed Ellsbury in 2013: in the bleachers of my high school football team’s game, jumping up and down in joy. That came crashing down after years of inconsistent, injury-plagued baseball marred Jacoby’s career. He actually wasn’t as bad as you might’ve thought, hitting .271 on his best year in the Bronx and .257 in his worst. But was that worth it for a $153 million contract over 7 years, 3 of which he was nowhere to be found? Absolutely not.

Johnny Damon

Winner: Tie

I examined a few criteria for this one. Firstly, Johnny Damon was pretty well-liked by both fan bases during his time in Boston & the Bronx. He still routinely comes back to Yankee Stadium for Old Timers’ Days and shows his face in Red Sox events. After breaking the Curse of the Bambino in 2004 - in part due to his grand slam in Game 7 of the ALCS - Damon hit .285 as a Yankee and was a key part of their 2009 World Series team. Alex Rodriguez even went as far as to say he was the X-factor in “lightening up the clubhouse,” alluding that the Yankees were too “Goldman Sachs” and that Damon helped them to loosen up a bit. You have to think Damon was a great asset for both sides.


Kevin Youkilis

Winner: Red Sox

I hated Youk since the day he was called up by the Sox in 2004, as he was a pretty big thorn in the side of Yankees pitchers. 2008 through 2010 featured him hitting at least .305 in every season, en route to a solid .281 career batting average. In 2012, he was traded to the White Sox, and then signed a one-year deal with the Bombers, finishing with a .219 average. I put my hatred aside and was rooting for him to do well, even buying a shirsey with his name on it in 2013. But unfortunately, a .219 average over 28 games defines a clear winner in this scenario - the team that he helped win 2 World Series in 8 years.

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