Red Sox-Yankees Rivalry: 9 Who Signed with the Dark Side for 2012

« Prev
1 of 10
Next »
Use your ← → (arrow) keys to browse the slideshow
Red Sox-Yankees Rivalry: 9 Who Signed with the Dark Side for 2012
Wade Boggs, in an image Red Sox fans will never forget. Photo by Ron Frehm/AP

As spring training starts baseball juices flowing, it's time for a look at the latest members of the "Benedict Arnold Club", as Matthew Kory of Over the Monster calls it.

If you're a New York fanatic, there's always a twinge when you see a former favorite wearing the Red Sox uniform: think Alfredo Aceves. Similarly, members of Red Sox Nation cringe at the thought of seeing someone like 2004 World Series hero Johnny Damon don the pinstripes.  

Making it worse for Red Sox fans is that the player movement along the Boston-New York corridor has been heavily in the Yankees favor over the years, starting with a guy named Babe Ruth.  

Of the defectors in the last 20 years, I would guess Roger Clemens and Wade Boggs sting the most from the Red Sox side. Everyone over 30 will probably remember when Boggs joined the Yankees in 1993. That was bad enough, but seeing him on that horse after winning the World Series just rubbed salt in the wound.

Reliever Mike Stanton is another Red Sox player who found success in the Bronx. At the 1996 trading deadline the Red Sox sent him to Texas for two forgettable players. The Yankees picked him up the following year, and over the next seasons he went 30-12 out of the NY bullpen, earning an All-Star nod in 2001.

From the Yankees side, there have been fewer defections that have come back to haunt them in the past few decades—Aceves and Mike Lowell being the most recent exceptions.

A couple of others that come to mind are David Cone and Don Baylor, thought by many to be the catalyst for the pennant-winning 1986 Red Sox team.

Some players performed reasonably well for both teams: David Wells, Mike Torrez, Ramiro Mendoza and Eric Hinske come to mind.

(In fact, those last two names are the answer to a pretty good trivia question: Who are the only two ballplayers since 1918 to have won a World Series ring with both the Red Sox and the Yankees?)

Others have played for the dark side at the end of their careers: Luis Tiant, Bill Monbouquette and George "Boomer" Scott had twilight stints with the Yankees, while I imagine Yankee fans found it difficult to watch the great Elston Howard play for the Red Sox.

In recent years free agency has created most of this movement, when the Yankees were quite simply willing to pay more than the Red Sox for certain players.

Even before free agency, however, the Yankees always seemed to get the better of the also-ran Red Sox. Many people forget that Babe Ruth was not the only player sold to the Yankees because of Harry Frazee's money woes in the World War I era. 

Duffy Lewis, Everett Scott, Ernie Shore, Herb Pennock and Carl Mays all contributed to the Red Sox winning five of the seven World Series played between 1912 and 1918. Kory points out they were all sold to the Yankees between 1919 and 1923, leading to the total dismantling of a Red Sox powerhouse that would not even become a .500 team again until 1935. (Of course, the Sox also sold the legendary Tris Speaker to Cleveland.)

Back in the day, Yankee star pitchers Red Ruffing and Waite Hoyt both came from Boston.

In 1967 the Yankees embarrassed the Red Sox by getting All-Star and Cy Young reliever Sparky Lyle in exchange for the immortal Danny Cater. 

A surprisingly high number of the 2004 curse-busting Red Sox team also played for the Yankees sometime during their careers. In addition to Damon and Mendoza, Mike Myers, Doug Meintkeiwicz, Mark Bellhorn, and Alan Embree all donned pinstripes at some point.

A few other club members whose names are familiar to most baseball fans are: Kevin Cash, Rick Cerone, Nick Green, Rickey Henderson, Jim Leyritz, Mike Stanley and Tom Gordon.

In all, according to, there are some 210 players over the years who have played for both teams.

Last year, the only former Red Sox player on the Yankees major league roster was Bartolo Colon, while Aceves was the only former Yankee on the Red Sox roster. Chances are those numbers will be higher this year.

Begin Slideshow »

Follow Boston Red Sox from B/R on Facebook

Follow Boston Red Sox from B/R on Facebook and get the latest updates straight to your newsfeed!

Boston Red Sox

Subscribe Now

By signing up for our newsletter, you agree to our Terms and Privacy Policy.

Thanks for signing up.