10 Biggest Red Sox 'Traitors' in Franchise History

Evan Brunell@evanbrunellFeatured ColumnistApril 22, 2014

10 Biggest Red Sox 'Traitors' in Franchise History

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    Every time a Red Sox player bolts town and dons pinstripes for the New York Yankees, fans of the Red Sox feel as if something sacrosanct has been violated.

    Red Sox fans are born and bred to consider the Yankees the enemy: For too many years, the Yankees rode high while the Red Sox rose and fell (mostly fell) in their quest for a World Series ring. From 1919 to 2003, New York garnered 26 World Series rings to Boston's zero and broke Sox fans' hearts countless times, most recently in 2003 when Aaron Boone's walk-off shot in Game 7 of the ALCS sent New York to the World Series.

    To add insult to injury, most of the Yankees' early championships were at the hands of former Red Sox player Babe Ruth, as well as many other ex-Red Sox that followed Ruth's exodus from Boston to New York. Later on, Red Ruffing and Sparky Lyle found success with New York, a team that seemed to churn out Hall of Famer after Hall of Famer, while Boston was left with Ted Williams.

    With the latest Red Sox "traitor" Jacoby Ellsbury returning to Fenway Park for the first time as a New York Yankee, here's a look at the 10 biggest traitors of all time: those who left Boston and ended up in New York by their own hand.

10. Kevin Youkilis

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    Associated Press

    We start with Kevin Youkilis, who made his debut with Boston and became a full-time player two years later. He earned three All-Star nods and won a Gold Glove at first base in 2007. That year, Youkilis was instrumental in keying Boston to its second World Series title of the 21st century.

    In 2012 with the Red Sox, Youkilis struggled to start the year. When he went down with injury, Will Middlebrooks stepped in and got off to such a roaring start that there was no question Middlebrooks deserved the job once Youkilis returned from the disabled list. Youkilis would finish the season with a .692 OPS for Boston while Middlebrooks had a .949 OPS the day Youkilis was traded. As a veteran, Youkilis could have made problems in the media and clubhouse about his marginalized role, but he chose to stay classy.

    On June 24, 2012, Youkilis was standing at third base after a triple in the seventh inning. Then-Sox manager Bobby Valentine pulled him from the game once it became apparent he was about to be traded to the Chicago White Sox. He raised his helmet to the cheering crowd, as the Associated Press writes, and disappeared down the Red Sox dugout, about to change his socks from red to white and join a different team.

    Feel-good goodbye stories don't seem to happen much for Red Sox players. Finally, the Fenway Faithful had one.

    Then Youkilis signed with the Yankees.

    The outrage wasn't palatable—after all, Boston had traded him away. Still, it was a jolt to see the former Red Sox third baseman appear at third for the Yankees. Boston fans felt they had closed the book on Youkilis with a happy ending only to see Youkilis add on an epilogue they didn't want to see.

9. Alan Embree

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    Jim McIsaac/Getty Images

    Alan Embree was one of the first trades executed by the Red Sox under the new John Henry ownership group. On June 23, 2002, Embree and prospect Andy Shibilo were dealt to Boston for prospects Brad Baker and Dan Giese. He quickly established himself as one of the better relievers in the bullpen. Equipped with a strong fastball, Embree pitched many high-leverage innings as a member of the setup corps.

    Embree is best remembered for being the man on the mound when the Red Sox vanquished the Yankees in Game 7 of the 2004 ALCS. Embree induced a ground ball from Ruben Sierra to second baseman Pokey Reese, then jumped into catcher Jason Varitek's arms and began to celebrate. Boston was headed to the World Series, which the Red Sox would go on to win for the first time since 1918.

    Embree was also the first 2004 world championship Red Sox to turn traitor.

    After beginning 2005 with a brutal 7.65 ERA in 37 and two-thirds innings for Boston, he was released. The New York Yankees promptly snapped him up, sticking a thumb in the eyes of the Red Sox. Embree pitched terribly in New York as well before going on to resurrect his career back in San Diego and, later, Oakland

    As the first Red Sox player to turn villain and don pinstripes just months after helping vanquish the Yankees and bring Boston its first World Series title since 1918, it was a tough pill to swallow. Mark Bellhorn was the next to follow, joining New York in August of 2005. Since then, four other 2004 Red Sox players have played for the Yankees at some point: Ramiro Mendoza, Johnny Damon, Kevin Youkilis and Derek Lowe.

8. Carl Mays

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    Mark Duncan

    Carl Mays (not pictured) is the next Red Sox traitor. He's more famous for being the unfortunate soul to have delivered the only pitch in baseball history that resulted in a fatality, as MLB.com relates. His Aug. 16, 1920 pitch for the New York Yankees to the Cleveland Indians' Ray Chapman resulted in Chapman's death.

    Mays was one of the most disliked players of his time, with F.C. Lane saying that Mays "aroused more ill will, more positive resentment than any other ballplayer on record," according to SABR.org. He added the Red Sox faithful to those who disliked Mays on July 13, 1919.

    Just months removed from being an integral part of the Sox's World Series victory in 1918, Mays was so fed up with the lack of run support he was receiving that he walked out in the middle of the July 13 game he was pitching, left the team and demanded a trade, as SABR.org relays.

    That trade was to the Yankees. 

    Mays would go on to win 80 games with the Yankees, the most for any team in his career, including a league-leading 27 in 1921. He would also earn a World Series ring with the team in 1923, the first of New York's 27.

7. Jacoby Ellsbury

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    John Minchillo

    Here's where the defections start getting meaningful. The Red Sox drafted, developed and cultivated Ellsbury into an All-Star center fielder who helped the team win two World Series rings.

    Then Ellsbury took his talents to New York, signing for seven years and $153 million. Ellsbury could have big things in store for him as a member of the Yankees, with a short porch in right field attracting home runs. He's also excellent on defense and has led the AL three times in stolen bases. 

    For the next seven years, Ellsbury will likely be a constant thorn in the side of the Red Sox. It will be all the more annoying that he came over from the Red Sox. 

    But Ellsbury doesn't rank lower on this list because the Red Sox never bothered to make an offer. After seeing their new mantra of avoiding long-term deals with oversaturated dollars work so well in 2013, all parties involved knew a return to Boston was extremely unlikely, as the Boston Herald wrote. The market would have had to work against Ellsbury to the point a five-year deal would have been on the table.

    Still, there's something jarring about seeing a clean-shaven Ellsbury appear in pinstripes. It's just wrong. It feels...traitorious.

6. Luis Tiant

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    Charles Krupa

    These days, Luis Tiant is a fixture at Fenway Park. You can often catch him outside the stadium near his concession stand, where he signs autographs. He's thrown out many a first pitch and frequently attends Red Sox games.

    Tiant was a solid pitcher for the Cleveland Indians and Minnesota Twins, but it wasn't until his arrival in Boston at age 30 that he broke out. In 1972, his second season with the team, he registered a league-leading 1.92 ERA. He would go on to spend eight years with the team and win 122 games, currently placing him fifth on the Red Sox all-time wins list.

    But Tiant isn't really considered Red Sox royalty. Could his defection to the Yankees have something to do with it? 

    As NESN remembers, Tiant spurned the Red Sox's one-year deal in the 1978-79 offseason in favor of New York's two-year offer. While Tiant wasn't the same pitcher with New York that he was with Boston, he still cobbled together solid seasons in the rotation and helped New York win 103 games in 1980.

5. Wade Boggs

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    Wade Boggs could have been a lifetime Red Sox player.

    Instead, thanks to an unexpected death of Red Sox owner Jean Yawkey, a contract offer was pulled by Yawkey's successors, as Boggs related to The Boston Globe. Boggs eventually landed with the New York Yankees (with the Los Angeles Dodgers also vying for his services) and was a member of the 1996 World Series team.

    While Boggs was only with the Yankees for five years to his 11 with the Red Sox, animosity against Boggs lingers to this day. 

    Roger Clemens' No. 21 has yet to be worn by another player since Clemens left Boston, but over a dozen players have worn Boggs' No. 26. Currently, backup infielder Brock Holt wears No. 26. 

    Boggs' number isn't retired either, despite meeting the two primary criteria of at least 10 years played with the Red Sox and election to the Baseball Hall of Fame. Previously, the player also had to have retired with the Red Sox. Technically, this criteria remains and has been relayed to Boggs as the primary reason his number has not been retired, according to the Globe. However, both Carlton Fisk and Johnny Pesky finished their playing careers elsewhere. Pesky eventually returned to the Red Sox as a coach, manager, broadcaster and special assistant, while Fisk was hired as a special assistant right before seeing his number retired.

    So clearly, the criteria is malleable. 

    Boggs just hasn't received any love from Red Sox fans, and a lot of it has to do with his much-publicized affair with Margo Adams, his continued involvement in Old-Timer's Day at Yankee Stadium and the famous photo above. Red Sox fans just can't reconcile a triumphant Boggs on a horse celebrating the World Series as a Yankee with his long history with the Red Sox, as Yahoo Sports notes.

    His defection to the Yankees certainly shouldn't be the only reason his number isn't retired. But being a traitor certainly doesn't help.

4. Ed Barrow

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    John Lindsay

    While Red Sox owner Harry Frazee was complicit in selling all his best players to the Yankees to help establish the New York dynasty, it was former Red Sox manager Ed Barrow who put it all together. Barrow was the architect of the Yankees from 1921 to 1945, winning 10 World Series. He is honored in the Hall of Fame, earning election in 1953.

    Before Terry Francona won a ring with the Red Sox in 2004, the last manager of Boston that held a ring was Barrow. After managing from 1918 to 1920, Barrow resigned and bolted to New York. He wasn't the first traitor to do that, but he certainly was the one who changed everything.

    Barrow began pilfering Boston of its best players: Waite Hoyt, Herb Pennock, Wally Schang, Everett Scott, Joe Dugan, Joe Bush and Sam Jones, among others, moved from Boston to New York and fueled New York's rise to the most elite team in the league, as the Baseball Research Journal, via SABR.org, writes. When New York won its first World Series in 1923, four of the five starting pitchers in the rotation and four of eight starting position players had all been acquired from Boston.

    The trades for Red Sox players were so lopsided, Barrow sent $305,000 to the Red Sox in what is believed to help make up for the imbalance, as the Baseball Research Journal states.

    Barrow was the one to recognize the value of the Red Sox players and acquire a wide swath of them. If Barrow had never left, it's entirely possible some players would have gone to other teams, while others would have stayed in Boston.

    In short, Barrow is the reason why the Yankees are the Yankees, and it took until the 21st century for Boston to reclaim its spot in baseball royalty.

3. Roger Clemens

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    Julie Jacobson

    Roger Clemens was a traitor to the Red Sox in two ways: spurning an offer to return to the Red Sox—twice—and not giving his all to the team in later years.

    The Red Sox offered Clemens "a substantial, competitive offer, by far the most money ever offered to a player in the history of the Red Sox franchise," as GM Dan Duquette told the Boston Herald at the time (quoted in MassLive.com). However, Clemens refused to sign and instead joined the Toronto Blue Jays on a four-year deal worth $40 million, sparking a renaissance.

    Clemens got in shape and was extremely motivated in Toronto, earning AL Cy Young Award honors for the two seasons he spent north of the border. Motivation was an issue in his later years for Boston, as well as reporting to spring training overweight, including in his contract season of 1996, as Dan Shaughnessy of The Boston Globe wrote.

    Then it happened.

    Roger Clemens was traded to New York, where he won two World Series titles. He would also turn in his final 20-win season in 2001, when he went 20-3 with a 3.51 ERA and earned his last Cy Young Award.

    Not since the days of Sparky Lyle had someone left Boston and enjoyed such strong success with the Yankees. The litany of accolades that followed Clemens when he left Boston opened a wound for Red Sox fans, who expressed anger at Clemens' lackadaisical work ethic in his later years with Boston.

    Clemens would later bolt New York and pitch for the Houston Astros for three seasons, helping thaw the relationship between the right-hander and Red Sox fans somewhat, as he came out of retirement after the 2003 World Series to sign with Houston. It was viewed as a bit of a snub of the Yankees, as he had communicated to New York that he was unequivocally retired and did not give the Yankees a chance to sign him when he chose to pitch again, per GM Brian Cashman, according to ESPN.

    After three years with Houston, Clemens had a chance to come home to Boston, where it all began...and spurned the team yet again. Clemens chose to join the Yankees on a prorated salary of $28 million, rejecting Boston's offer of $20 million, as CNN reports. That would be it for Clemens, who retired as a Yankee following the 2007 season.

    Traitor, yet again.

2. Babe Ruth

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    The original traitor lands at No. 2 on the list.

    Why is he a traitor if Red Sox owner Harry Frazee sold his contract to the Yankees, you might ask.

    For one, he refused to play for the Red Sox unless they doubled his salary. It wasn't the first time he negotiated for salary: It was a frequent topic between Frazee and Ruth, as SABR.org recollects. Ruth also wouldn't adhere to team policies, such as a nightly curfew, and would regularly skip games as he pleased, including the final game of the 1919 season, Diary of a Red Sox Season: 2007 relays.

    As a result, just two years after Frazee dismissed any thought of trading Ruth, he was sent to New York.

    When news of Ruth's sale to the Yankees broke, opinion was divided in Boston, with several amazed the Red Sox could give up such a talent, while others, including former players, were glad to be rid of the "egomaniac," as SABR notes.

    But Ruth would go on to become the best player in the game and is still considered by many to be the best who ever stepped on a baseball field. He hit home runs with impunity and sparked the Yankees on the way to their dynasty that spanned decades.

    If Ruth hadn't been so aggressive in demanding salary raises, it's possible he would have remained at the Red Sox for longer.

    Ruth doesn't deserve to be No. 1 on this list, though, because Red Sox owner Harry Frazee contributed to Ruth's sale by overextending his finances, necessitating a sale of his best ballplayers in order to generate revenue, which you can read about in detail at SABR.org.

1. Johnny Damon

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    Al Bello/Getty Images

    And here we are, the biggest Red Sox traitor of all time.

    Every other person on this list has something that dulls his traitor label:

    • Kevin Youkilis was traded from the Red Sox and did not perform in a Yankees uniform.
    • Alan Embree was released from the Red Sox and fared poorly with the Yankees.
    • Carl Mays comes close but had his best years with Boston, and by the time New York won the World Series, he was an afterthought on the squad.
    • Jacoby Ellsbury never received a contract offer from the Red Sox.
    • Luis Tiant was fading and has earned back his credentials with the Red Sox as he has been a much bigger presence representing the Red Sox brand than the Yankees.
    • Wade Boggs would have re-signed with Boston had Jean Yawkey's offer stood. But he comes close to Damon.
    • Barrow was not a player. Fair or not, this list is primarily concerned with traitorous players.
    • Roger Clemens at least padded his transition from Boston to New York with a stop over in Toronto. But like Boggs, he comes close.
    • Babe Ruth was sold, and the Red Sox owner's finances were a big part of the reason, even if Ruth didn't help matters.

    That leaves Damon. So why is Damon the biggest traitor in Red Sox history?

    For one, there's this quote uttered in May 2005 to MLB.com's Alan Eskew:

    There's no way I can go play for the Yankees, but I know they are going to come after me hard. It's definitely not the most important thing to go out there for the top dollar, which the Yankees are going to offer me. It's not what I need.

    What did Damon do? Took top dollar. From the Yankees.

    The second thing he did was spurn the Red Sox's offer of four years and $40 million. If being paid top-dollar wasn't important to him, that was a pretty good payday. Instead, he took four years and $52 million from the Yankees. He would also contribute to the 27th World Series championship for New York, earned in 2009.

    To add insult to injury, Damon played better for the Yankees than he did with the Red Sox, hitting more home runs thanks to the short porch in right field:

    NYY (4 yrs)57625254106367729693.285.363.458.821112
    BOS (4 yrs)59727824617305629998.295.362.441.803108

    To boot, there was just something wrong about Damon's caveman look disappearing into a clean-shaven face.

    Damon was roundly booed in all his return trips to Fenway Park and is still persona non grata for fans, who have long memories.

    But Damon wasn't done spurning Boston. While with the Tigers in 2010, the Red Sox claimed Damon on waivers, hoping he could help spark a team that had been beset by injuries. While Damon could have accepted the claim and rejoined the Red Sox in the midst of a wild-card race, he chose to stay in Detroit, as ESPN Boston reported.

    Damon said that how his departure from Boston was handled complicated the issue, Tyler Kepner of The New York Times wrote

    It was a mistake by Damon, who would have been welcomed back with open arms, because it would have been his decision to come back to Boston. But now, it "will stand as the final unforgivable act for a fan base that feels scorned once again," according to Sports Illustrated.

    And so Damon stands atop the heap as the biggest Red Sox traitor.


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