The 15 Biggest Players and Coaches Who've Crossed Enemy Lines
There are a lot of players and coaches who have crossed into enemy territory over the years. It’s not pretty, but sometimes it happens. A beloved player or coach ends up with a hated rival.
I’m not talking about Babe Ruth, whose owner decided to sell him, or Chris Chelios, whose team decided to trade him. And I’m not talking about David Aardsma (Who? Exactly.)
I’m talking about the Johnny Damons and Nick Sabans of the world—the top talent who left of their own free will and chose to join the enemy ranks.
To review, we’re looking for the following: Big name, big rivalry, went willingly.
Honorable Mention: Jerry Rice
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San Francisco and Oakland teams are generally rivals just because of the Bay Area connection, but I wouldn’t say the 49ers and Raiders hate each other to the level of some teams. This one gets an honorable mention because it’s a lukewarm rivalry, but it’s a huge name.
Jerry Rice might be the best wide receiver in NFL history, and he made most of his catches with the 49ers. After 16 years with the team and a couple of declining seasons, Rice went across the bay to sign with Oakland.
Honorable Mention: Terrell Owens
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Terrell Owens played for the Philadelphia Eagles in 2004 and ’05. In 2004, he racked up 1,200 receiving yards and was selected for the Pro Bowl.
Despite his talent, Owens' relationship with the team was tumultuous. In 2006, he became a free agent and joined Jerry Jones' Dallas Cowboys.
This one gets an honorable mention because T.O.’s exit from Philly wasn’t exactly voluntary—the team released him after repeated behavioral issues became too much to handle.
Eric Mangini
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Eric Mangini coached defensive backs for the New England Patriots from 2000-05 under head coach Bill Belichick. The two were friends, but in 2006, Mangini left to accept the head coaching position with the New York Jets.
Not only did Mangini leave for a rival, but he spilled some beans about Spygate, too.
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Brett Favre
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Although the Green Bay Packers might have a bigger blood feud with another NFC North team, the Minnesota Vikings are still a division rival.
Brett Favre played 16 years with the Packers, and the 11-time Pro Bowler was as beloved as they come in Green Bay. After a lot of uncertainty over his retirement, Favre left the Packers and signed with the Jets in 2008. Worse, he signed with the Vikings in the following year.
Orel Hershiser
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Orel Hershiser pitched for the Los Angeles Dodgers from 1983-94 (and again in 2000) and won a Cy Young there. He won 204 games and posted a 3.48 ERA over his 18-year MLB career.
After 1994, Hershiser played three seasons in Cleveland and then signed with the San Francisco Giants as a free agent in 1998. The Giants signed Hershiser to a one-year, $3.45 million deal with an option for 1999 but cut ties after a disappointing season.
Rod Woodson
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The Baltimore Ravens and Pittsburgh Steelers have one of the most intense rivalries in football.
Hall of Fame cornerback Rod Woodson was the Steelers’ first-round draft pick in 1987. He played in Pittsburgh for 10 seasons before becoming a free agent in 1997.
Woodson played one year in San Francisco before signing with the Baltimore Ravens for four years and $11.5 million. He was a crucial part of Baltimore’s Super Bowl-winning season in 2000.
Jacoby Ellsbury
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All-Star outfielder Jacoby Ellsbury got his start with the Boston Red Sox and played there from 2007-13. He was a part of two World Series championship teams.
Ellsbury became a coveted free agent following the Red Sox 2013 World Series season, and the New York Yankees swooned. The two sides reached an agreement on a seven-year, $153 million deal in the offseason.
Deion Sanders
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Deion Sanders bounced around—in both cities and sports—but he did spend five years with the Dallas Cowboys from 1995-99. So it was a pretty big burn when he signed a big free-agent deal with the hated rival Washington Redskins in 2000. The deal was worth $56 million over seven years, but Sanders only ever played one season in Washington.
Bill Sharman
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Bill Sharman played for the Boston Celtics from 1951-61. He played in eight All-Star games and won four NBA championships, including the 1959 defeat of the Los Angeles Lakers, a budding rival.
After his playing career, Sharman went into coaching, and he was the Lakers' top guy from 1971-76. He was inducted into the Hall of Fame as both a player and a coach.
Marian Hossa
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Few sports rivalries are more intense than Original Six feud between the Detroit Red Wings and Chicago Blackhawks.
Marian Hossa started his All-Star NHL career with the Ottawa Senators. He played there for seven seasons before moving on to Atlanta, Pittsburgh and eventually Detroit.
Hossa played just one season in Detroit, but that was enough to make the 12-year, $62.8 million deal he signed with the Blackhawks in 2009 sting.
Brian Wilson
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One could argue that the rivalry between the Los Angeles Dodgers and San Francisco Giants is up there with the Yankees/Red Sox.
Brian Wilson was an All-Star with the Giants—he pitched there from 2006-12 and was instrumental in the team’s 2010 World Series victory.
Wilson had season-ending Tommy John surgery in 2012, and the Giants did not re-sign him after the season. Instead, he ended up in L.A. with his rivals to the south.
Bill Belichick and Bill Parcells
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Bill Belichick served as an assistant coach under Bill Parcells with the New England Patriots in 1996 and then went with him to their division rival New York Jets in 1997.
The two coached together in New York from 1997-99. When Parcells announced his retirement, Belichick was set to replace him as head coach, but he bolted back to New England after just one day on the job.
Oh, and Parcells also coached both the New York Giants and Dallas Cowboys, two teams that don’t exactly like each other.
Wade Boggs
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It’s one thing for a member of the Boston Red Sox to become a New York Yankee—it’s another for one to do it so willingly. Wade Boggs played his first 11 MLB seasons in Boston, but in 1992, he signed as a free agent with the Yankees. The deal was for three years and $11 million.
Boggs continued his productive ways in New York, batting .313 in five years there and helping the team win a World Series title in 1996.
Tom Landry
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Admittedly, when Tom Landry played for the New York Giants, the Dallas Cowboys weren’t a rival. In fact, they weren’t even a franchise. All the same, Landry played for the Giants from 1950-55. After his playing career, he became an assistant coach with the team until 1959.
In 1960, Landry left New York to become head coach of the new Cowboys franchise. Landry coached in Dallas for almost 30 years but was eventually fired by Jerry Jones in 1989. According to Bart Hubbuch of the New York Post, Landry wasn’t pleased with Jerry Jones’ handling of the situation, and he spent the remainder of his life rooting for the Giants.
Nick Saban
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Nick Saban has bounced around the football coaching world, from college to the NFL and back. However, the important facts to know are these: Saban coached at SEC powerhouse LSU from 2000-04. After a two-year stint with the Miami Dolphins, Saban returned to college to coach another SEC powerhouse, the Alabama Crimson Tide.
Luis Figo
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Luis Figo is hoping to become FIFA’s next president, but some fans in Barcelona might still think of him as a traitor.
The beloved footballer played 172 La Liga games for Barcelona and scored 30 goals. He helped the team win two Copa del Reys. But in 2000, he took a lot of money to play for Barca’s fiercest rival, Real Madrid, when Real’s new team president activated his buyout clause.
According to Tom Adams of ESPN FC, then-Barcelona president Joan Gaspart said at the time, “I'll not forget this. Whoever is responsible for this will pay for it. We'll see how and when.”
Johnny Damon
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Of all the players who have left Boston for New York over the years, for one reason or another, Red Sox fans seem to have a particular disdain for Johnny Damon.
Damon had four productive years in Boston from 2002-05, and he was part of the 2004 team that broke the infamous World Series curse. However, Damon became a free agent in 2005, and the Yankees scooped him up for four years and $52 million.
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