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Jonathan Daniel/Getty Images
Rivalries are a cornerstone of professional sports. When players sign with a particular team, they recognize what opponent is most meaningful to their supporters and even the franchise itself.
But sometimes, a player experiences that passion from both sides of the rivalry during their career.
This is by no means an exhaustive list of players who have had that experience, though we tried to focus on marquee names while including multiple players as possible.
Additionally, the list of rivalries is hand-picked. There are dozens of matchups to potentially feature, but we focused on the five most commonly known professional sports: baseball, basketball, football, hockey and soccer.
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Andrew Benintendi | Jim McIsaac/Getty Images
Prior to the 2022 trade deadline, outfielder Andrew Benintendi joined the list of those to suit up for both the Boston Red Sox and New York Yankees.
And he’s now part of a lengthy, star-studded list.
Legendary pitcher Roger Clemens won a Cy Young on both sides of the rivalry. Hall of Fame third baseman Wade Boggs was a perennial All-Star with the Sox and Yankees. Johnny Damon played an integral role in Boston’s epic run to the 2004 World Series, then bolted for New York and later won another ring on the Yankees.
Oh, and some old guy named Babe Ruth pretty famously went from Boston to New York and sparked 80-plus years of superstition that Damon helped end.
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Joc Pederson | Ronald Martinez/Getty Images
More than 200 players have donned the colors of both the Los Angeles Dodgers and San Francisco Giants. So, hey, if a certain player seems excluded, know it’s a substantial field of options.
Hall of Fame outfielder Duke Snider, All-Star outfielder (and now Houston Astros manager) Dusty Baker and Cy Young-winning pitcher Orel Hershiser spent a majority of their rivalry time in Dodger Blue but played one season in San Francisco.
From the opposite view, Hall of Fame pitcher Juan Marichal and All-Star hurler Jason Schmidt thrived with the Giants prior to career sendoffs in Los Angeles.
Stolen-base machine Brett Butler and All-Star second baseman Jeff Kent had the most balanced contributions.
The most recent example is outfielder Joc Pederson.
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Julius Peppers | David Banks/Getty Images
Since 1921, the Chicago Bears and Green Bay Packers have practically squared off twice per year in every season.
During the Brett Favre and Aaron Rodgers eras, the rivalry has leaned decidedly in Green Bay’s favor. Before then, though, the Bears dominated each decade other than the Vince Lombardi-led Packers’ peak in the 1960s.
In recent years, edge-rusher Julius Peppers is the most notable player to appear on both sides. He was an All-Pro in Chicago and a Pro Bowl choice with the Packers.
Adrian Amos, Martellus Bennett, Ha Ha Clinton-Dix, Jimmy Graham, Lucas Patrick and Josh Sitton all crossed sides in the 2010s and 2020s, too.
Jim McMahon, the quarterback of the Bears’ iconic Super Bowl win in 1985, also served as a backup to Favre in Green Bay.
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James D. Smith /Icon SMI/Icon Sport Media via Getty Images
Hall of Fame wide receiver Terrell Owens is best recognized for his dominance with the San Francisco 49ers. And, hey, the rivalry between the 49ers and Dallas Cowboys also features Hall of Fame cornerback Deion Sanders on either side.
Owens also pulled off a memorable double with the Cowboys and Philadelphia Eagles.
In 2004, he landed first-team All-Pro recognition as a member of the Eagles’ NFC-winning team. Three seasons later in Dallas, he again reeled in first-team honors.
All-Pro quarterback Randall Cunningham, wideout Harold Carmichael and receiver Tommy McDonald each had prolific Eagles careers with a stop in Dallas. All-Pro running back DeMarco Murray is the most notable name that went the opposite direction.
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Shaquille O’Neal and Kobe Bryant | Noah Graham/NBAE via Getty Images
One of the most historic rivalries in sports, the Boston Celtics and Los Angeles Lakers have a long history of championship duels. They commonly met in the NBA Finals during the 1960s and 1980s, but they had little crossover beyond Hall of Famer Bob McAdoo’s 20-game stint in Boston.
The best player to play for both sides—with absolutely no hesitation—is Hall of Fame center Shaquille O’Neal.
Shaq played eight years in L.A., winning three NBA titles, three NBA Finals MVPs and one regular-season MVP. He spent the final season of his career in Boston.
Seattle SuperSonics legend Gary Payton used a ring-chasing year on both franchises, too. Avery Bradley, Rajon Rondo and Isaiah Thomas are otherwise the most recognizable recent names.
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Marian Hossa (81) and Chris Chelios (24) | Dave Reginek/NHLI via Getty Images
One disclaimer: The rivalry with the Chicago Blackhawks has dwindled since the Detroit Red Wings moved to the Eastern Conference. At its peak, though, it was a bitter matchup that dated back to the NHL’s Original Six era.
Chris Chelios played in Chicago, then Detroit. Marian Hossa made the opposite move.
The parallels in their Hall of Fame careers are remarkable, too. They starred with the Montreal Canadiens and Ottawa Senators, respectively, before making their way to this rivalry. Neither player won a championship at the earlier stop, but both hoisted the Stanley Cup at the second.
Wildest part of all? They shared the ice during Chelios’ final and Hossa’s lone season in Detroit, and the Wings toppled the Blackhawks to win the Western Conference.
Bob Probert and Stu Grimson, a pair of enforcers, wore both sweaters in the 1990s, while Pius Suter and Dominik Kubalik are recent Chicago-to-Detroit defectors.
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Luis Figo | Eddy LEMAISTRE/Corbis via Getty Images
The story of Luis Figo summarizes this rivalry.
From 1995 to 2000, the attacker was a beloved star for FC Barcelona. But in the summer of 2000, he left for La Liga nemesis Real Madrid. During his first appearance back at Barcelona, fans threw everything from a whiskey bottle and fruit to a severed pig’s head.
Figo played for Real until 2005, earning FIFA World Player of the Year honors in 2001.
Also of note, Figo played alongside Brazilian legend Ronaldo at Barcelona in 1996-97 and Real from 2002 to 2005. Ronaldo won FIFA World Player of the Year at both clubs.
Luis Enrique, Michael Laudrup and Javier Saviola are among the other notable players for both rivals.