They saw both sides of Yanks-Red Sox rivalry

July 28th, 2022

The Red Sox and Yankees have one of baseball’s most storied rivalries, and each franchise has had its share of iconic figures. Boston with Ted Williams, Carl Yastrzemski and David Ortiz. New York with Joe DiMaggio, Mickey Mantle and Derek Jeter.

Then there are the stars who experienced the rivalry from both sides.

Left fielder Andrew Benintendi will become the latest player to join the long list of guys who have suited up for both clubs after New York acquired him from the Royals on Wednesday. Benintendi was selected by the Red Sox with the seventh overall pick in the 2015 MLB Draft and spent his first five seasons in Beantown, most notably finishing second to new teammate Aaron Judge in the 2017 AL Rookie of the Year race and helping Boston win the 2018 World Series championship.

These are some of the biggest names to switch allegiances in the Red Sox-Yankees rivalry.

Don Baylor, DH
After concluding a six-year stint with the Angels that included an AL MVP Award in 1979, Baylor joined the Yankees as a free agent. Baylor spent three seasons with New York and won two Silver Slugger Awards before being traded to Boston for Mike Easler in 1986, marking a rare swap between the rivals. Baylor hit 31 homers for the Red Sox in 1986, winning another Silver Slugger, before posting a 1.046 OPS against the Angels in the ALCS as Boston won the AL pennant. The Red Sox traded Baylor to the Twins late in the 1987 campaign, and he won a World Series title with Minnesota the following month. He also played in the World Series with the A’s in a losing effort in 1988. Baylor and Eric Hinske (2007-09) are the only players to appear in three consecutive World Series with three different teams.

Wade Boggs, 3B
Boggs earned five batting titles, eight All-Star selections and six Silver Slugger Awards over 11 seasons with the Red Sox, but when he reached free agency after the 1992 season, he was coming off a career-low .259 average and .711 OPS. Looking to end an 11-year postseason drought, the Yankees took a chance on the aging third baseman, signing him to a three-year, $11 million contract. Boggs rebounded to hit .313/.396/.407 across five seasons with New York and won a World Series title in 1996, famously hopping on a police horse for a victory lap around Yankee Stadium during the post-clinch celebration.

Jack Chesbro, RHP
A member of the National Baseball Hall of Fame, Chesbro pitched for the Yankees (then known as the Highlanders) from 1903-09 and owns the Modern Era (since 1900) record for wins (41), starts (51) and complete games (48), all set in 1904. Chesbro was waived and claimed in September 1909 by the Red Sox, who trotted out the pitcher to start against the Highlanders in Game 1 of a doubleheader on the last day of the regular season. It turned out to be the final appearance of Chesbro’s career.

Roger Clemens, RHP
Clemens’ 13-year stint with the Red Sox included an AL MVP Award, three Cy Youngs, two 20-strikeout games, 192 wins and a 144 ERA+. But when he reached free agency after the 1996 season, Clemens was insulted by Boston’s initial offer and ultimately departed to sign a three-year deal with the Blue Jays. Clemens won the AL Cy Young Award in each of the first two years of the contract, reestablishing himself as an elite ace after showing signs of decline at the tail end of his Red Sox career. The Yankees, who were a free-agent suitor for Clemens before he signed with the Blue Jays, reached a blockbuster trade with Toronto in February 1999, sending David Wells, Graeme Lloyd and Homer Bush to the Jays for Clemens. The right-hander won two World Series titles and a Cy Young Award with the Yanks and also set multiple milestones in pinstripes, including career win No. 300 and strikeout No. 4,000 in the same game in 2003.

David Cone, RHP
After stints with the Royals, Mets and Blue Jays, Cone joined the Yankees prior to the 1995 Trade Deadline in a four-player deal. Cone won four World Series titles and threw a perfect game with the Bronx Bombers, but after the righty went 4-14 with a 6.91 ERA in 2000, the Yanks opted not to bring him back in free agency. Cone found a home with the Red Sox and recorded a 4.31 ERA over 25 starts for the club in 2001, including a Sept. 2 outing against the Yankees at Fenway Park in which he tossed 8 1/3 strong innings in a 1-0 loss opposite Mike Mussina, who fell one strike short of a perfect game.

Johnny Damon, OF
Boston reeled in Damon for $31 million over four years when the center fielder became a free agent after the 2001 season. Damon’s personality and production out of the leadoff spot made him eminently popular in Boston, and he helped the Red Sox put the finishing touches on their historic 2004 ALCS comeback against the Yankees with two homers, including a second-inning grand slam, in Game 7. It was more of the same after Damon signed with the Yankees. He hit .285 with 77 homers, 93 steals and an .821 OPS over four seasons with New York and won another World Series title during his final year with the club in 2009.

Jacoby Ellsbury, OF
Signing Damon away from the Red Sox worked out well for the Yankees, but Ellsbury? Not so much. For $153 million over seven years, New York got 520 games, 39 homers, a .716 OPS and 9.8 wins above replacement (according to Baseball-Reference) from the center fielder, who tallied just 13 postseason plate appearances as a member of the Yankees. With the Red Sox from 2007-13, Ellsbury produced a .789 OPS and 21.4 bWAR over 715 games and contributed to two World Series championships.

Rickey Henderson, OF
Henderson spent the majority of his career with the A’s, appearing in 14 seasons across four stints with the team, but the Yankees and Red Sox were among his other stops on the road to the Hall of Fame. Henderson spent five seasons with the Bronx Bombers between his first and second A’s stints, earning All-Star appearances in four of them. More than a decade later, Henderson played 72 games for Boston as a 43-year-old in 2002.

Waite Hoyt, RHP
Nearly a year after another, infinitely more famous deal between the two sides, the Red Sox and Yankees came together for an eight-player trade that brought Hoyt, at the time a 21-year-old with 227 2/3 innings under his belt, to the Bronx. Hoyt burnished his Hall of Fame credentials during his 10 seasons with the Yankees, going 157-98 with a 3.48 ERA and winning three World Series titles.

Elston Howard, C
The first Black player in Yankees history, Howard joined the club in 1955 and became a perennial All-Star, culminating with an AL MVP Award in 1963. New York traded the aging catcher to Boston for Ron Klimkowski and Pete Magrini in 1967, and after appearing in the World Series for the Red Sox against the Cardinals, Howard remained with the team for his final MLB season in 1968.

Mike Lowell, 3B
Lowell spent most of his career with the Marlins and Red Sox, but he was initially a Yankees farmhand and played eight games for New York during the 1998 season before being traded to South Florida in an ill-fated deal for Todd Noel, Mark Johnson and Ed Yarnall. After blossoming into an All-Star with the Marlins and contributing to the club's 2003 World Series win over the Yankees, Lowell was traded to Boston with Josh Beckett and Guillermo Mota for Hanley Ramirez, Aníbal Sánchez and two others following the 2005 season. In his second year with the Sox, Lowell hit .324 with 21 homers and 120 RBIs in the regular season and added a .353 average with two homers and 15 RBIs during the playoffs, earning World Series MVP honors as Boston won its second championship in four years.

Sparky Lyle, LHP
Traded to the Yankees after five solid seasons with the Red Sox, Lyle made a name for himself both on and off the field during his time in pinstripes. The left-hander became the first American League reliever to win a Cy Young Award in 1977 and co-authored “The Bronx Zoo,” a tell-all book chronicling the Yankees’ contentious 1978 season.

Herb Pennock, LHP
Acquired from Boston for Norm McMillan, George Murray, Camp Skinner and cash prior to the 1923 season, Pennock paid immediate dividends for the Yankees, going 19-6 with a 3.13 ERA in his first season as New York won the AL pennant. Pennock also went 2-0 with one save over three appearances in the 1923 World Series, helping the franchise win its first championship. Pennock, who won three World Series titles over 11 seasons with the Yankees, was inducted into the Hall of Fame in 1948.

Red Ruffing, RHP
Like Hoyt and Pennock, Ruffing pitched for the Red Sox before being traded to the Yankees and reaching new heights en route to the Hall of Fame. On top of his 231-124 record and 3.47 ERA in the regular season over 15 years with the Yankees, Ruffing recorded a 2.52 ERA across 85 2/3 innings in the World Series and won six titles.

Babe Ruth, OF/LHP
In arguably the most historically significant transaction in baseball history, the Red Sox sold Ruth to the Yankees for $100,000 in December 1919. Initially a star pitcher, Ruth helped the Red Sox win three World Series titles and was starting to establish himself as a two-way threat when Boston sent him to New York. Ruth became a full-time outfielder and reached unprecedented heights at the plate with the Yankees, producing a .349/.484/.711 slash line and hitting 659 homers over 15 seasons with the team. The Great Bambino also ushered in an era of newfound success for the Yankees, who won their first World Series title in 1923 and added three more during Ruth’s tenure. Meanwhile, Boston went 86 years without a championship, a drought blamed on a curse brought about by the sale of Ruth to New York.

Luis Tiant, RHP
Known for a distinctive windup that saw him twist and turn until his back was fully facing the hitter, Tiant recorded a 3.30 ERA, 2,416 strikeouts and 66.1 bWAR across 19 seasons, eight of them with the Red Sox. After his age-37 season in 1978, the righty jumped ship to the Yankees, with whom he posted a 4.31 ERA over two seasons.

David Wells, LHP
Wells was a key member of the Yankees’ rotation in 1997-98, and after being traded to the Blue Jays in the deal for Clemens, the fun-loving lefty returned to New York for two additional seasons (2002-03). Wells pitched for the Padres in 2004, then joined the defending World Series-champion Red Sox for the 2005 campaign, initially opting to wear No. 3 in honor of Ruth before swapping with teammate Edgar Renteria for No. 16 in an effort to change his luck during a rough stretch.

Kevin Youkilis, 1B/3B
After watching from the bench as the Red Sox won the 2004 World Series, Youkilis played a larger role in the team's 2007 championship. A fan favorite in Boston for his hard-nosed play, the man known affectionately as "Youk" hit .287/.388/.487 over nine seasons with the Red Sox before the club traded him to the White Sox in 2012. The Yankees brought in Youkilis as a free agent for the 2013 campaign, but he posted a .648 OPS and underwent season-ending back surgery after just 28 games. Following a season in Japan, Youkilis announced his retirement in 2014.