10 MLB Stars Who Won the World Series After Leaving the Yankees

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The New York Yankees have won a record 27 World Series. Their first Fall Classic triumph came in 1923, and their last was in 2009. Legendary baseball players like Babe Ruth, Alex Rodriguez and many more tasted ultimate baseball glory with the Bronx Bombers.

The Yankees have appeared in the World Series 41 times. For context, the Los Angeles Dodgers sit second with 23, roughly half of the New York franchise.

Still, many MLB stars couldn’t win the Fall Classic during their stint with the Yankees. Moreover, they won it after leaving them. Let’s take a look at 10 such players.

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10. Jordan Montgomery

The dependable left-handed starting pitcher was traded away by New York in 2022 and went on to anchor the Texas Rangers' rotation during their historic 2023 World Series championship run. - Source: Imagn — The dependable left-handed starting pitcher was traded away by New York in 2022 and went on to anchor the Texas Rangers’ rotation during their historic 2023 World Series championship run. – Source: Imagn

Jordan Montgomery played for the New York Yankees from 2017 to 2022. The Yankees entered the postseason in these six years, but failed to go past the American League Championship Series. They lost three times (in 2017, 2019 and 2022) to the Houston Astros in the ALCS.

Montgomery won his first and only World Series to date with the Texas Rangers in 2023. He pitched Game 2 of the Fall Classic against the Arizona Diamondbacks. He allowed four runs on nine hits across six innings. The Rangers lost the game.

9. Andrew Heaney

The resilient left-handed pitcher bounced back from an ERA over 7.00 in the Bronx to serve as a versatile starter and reliever for the 2023 World Series champions. - Source: Imagn — The resilient left-handed pitcher bounced back from an ERA over 7.00 in the Bronx to serve as a versatile starter and reliever for the 2023 World Series champions. – Source: Imagn

Andrew Heaney had a brief and difficult stint with the Yankees in 2021. He joined the Bronx Bombers via trade from the Los Angeles Angels on July 30, 2021. He made 12 appearances for the team, but the AL East team DFA’d him on Oct. 5, 2021. The Yankees lost the AL Wild Card Series in 2021.

Heaney won the 2023 World Series with the Texas Rangers. He appeared in Game 1 as a relief pitcher and tossed 0.2 scoreless innings. He later pitched five innings as a starter in Game 4. The Rangers won both games.

8. Nathan Eovaldi

A two-time All-Star and elite postseason ace, Eovaldi overcame multiple Tommy John surgeries to win World Series rings. - Source: Imagn — A two-time All-Star and elite postseason ace, Eovaldi overcame multiple Tommy John surgeries to win World Series rings. – Source: Imagn

Nathan Eovaldi played for the Yankees from 2015 to 2016. He joined the Bronx Bombers via trade from the Miami Marlins in December 2014. The Yankees reached the ALWCS in 2015, but couldn’t make the postseason in 2016.

The AL East team released Eovaldi in November 2016. He has won two World Series since then. First, with the Boston Red Sox in 2018, and then with the Texas Rangers in 2023.

Eovaldi tossed a scoreless inning each as a relief pitcher in Game 1 and Game 2 in 2018. Boston won both games. He also pitched more than six innings in Game 3 as a relief pitcher, but Boston lost.

In 2023, Eovaldi started Game 1, tossing 4.2 innings. He gave up five runs, but the Rangers won in extra innings. He later started Game 5, tossing six scoreless innings. Texas won the game and clinched the series.

7. Steve Pearce

A true journeyman who played for every AL East franchise, Pearce achieved baseball immortality by winning the 2018 World Series MVP. - Source: Imagn — A true journeyman who played for every AL East franchise, Pearce achieved baseball immortality by winning the 2018 World Series MVP. – Source: Imagn

Steven Pearce’s brief stint with the Yankees took place in 2012. He played 12 games for the Bronx Bombers and hit a solitary dinger. The AL East team designated him for assignment on Sep. 25, 2012, and the Baltimore Orioles claimed him.

Six years after the Yankees DFA’d him, Pearce won the 2018 World Series with the Boston Red Sox. He played all five games, batting .333 with three home runs and eight RBIs. The stellar performances earned him the 2018 World Series MVP Award.

6. Lance Berkman

The spectacular six-time All-Star switch-hitter drove in over 1,200 career runs and won the 2011 MLB Comeback Player of the Year. - Source: Imagn — The spectacular six-time All-Star switch-hitter drove in over 1,200 career runs and won the 2011 MLB Comeback Player of the Year. – Source: Imagn

Lance Berkman joined the Yankees via trade from the Houston Astros on July 31, 2010. He appeared in the 2010 ALDS and ALCS with the Yankees and entered free agency.

Berkman signed with the St. Louis Cardinals in December 2010 and won the 2011 World Series with them. His iconic moment came in Game 6 in the bottom of the 10th inning.

Berkman hit a two-out, game-tying RBI single to center field, and the Cardinals eventually won the game, forcing a Game 7. He had earlier hit a two-run home run in Game 6.

5. Jose Contreras

Jose Contreras joined the Yankees on a four-year, $32 million contract in December 2002. He played for the Bronx Bombers in the 2003 and 2004 seasons. The Bronx Bombers traded Contreras to the Chicago White Sox on July 31, 2004.

Contreras won the Fall Classic with the White Sox in 2005. He started Game 1, tossing seven innings in the AL Central team’s 5-3 win over the Houston Astros.

4. Lee Mazzilli

The popular All-Star switch-hitter carved out a reputation as an elite pinch-hitter, delivering clutch hits off the bench. - Source: Imagn — The popular All-Star switch-hitter carved out a reputation as an elite pinch-hitter, delivering clutch hits off the bench. – Source: Imagn

Lee Mazzilli played a short stint with the Yankees in 1982. He joined the AL East team via trade from the Texas Rangers in August 1982. The Yankees traded him to the Pittsburgh Pirates before the 1983 season.

Mazzilli won the 1986 World Series with the New York Mets. The NL East team used him as a pinch-hitter and late-game substitute. He hit .400 across four games.

3. Dave Winfield

The legendary Hall of Fame outfielder, 12-time All-Star and seven-time Gold Glover broke a career-long championship drought in 1992. - Source: Imagn — The legendary Hall of Fame outfielder, 12-time All-Star and seven-time Gold Glover broke a career-long championship drought in 1992. – Source: Imagn

Dave Winfield played for the Yankees from 1981 to 1988 and briefly in 1990. His relationship with owner George Steinbrenner was adversarial. Winfield reached the World Series in 1981 with the Yankees, but couldn’t make the postseason in the subsequent years.

The Bronx Bombers traded him to the California Angels in May 1990. Winfield won the World Series with the Toronto Blue Jays in 1992. He hit his first career World Series extra-base hit in Game 6.

2. Carlos Beltran

The nine-time All-Star, three-time Gold Glove winner and Hall of Fame outfielder capped off his illustrious 20-year career by winning his sole World Series ring. - Source: Imagn — The nine-time All-Star, three-time Gold Glove winner and Hall of Fame outfielder capped off his illustrious 20-year career by winning his sole World Series ring. – Source: Imagn

Carlos Beltran joined the Yankees on a three-year, $45 million contract. He played until Aug. 1, 2016, when he was traded to the Texas Rangers. During his time, the Yankees reached the postseason only in 2015.

Beltran later won the World Series with the Houston Astros in 2017 and retired. He was mostly used as a pinch hitter, and he went hitless in three at-bats.

Beltran had played in the 2013 World Series with the St. Louis Cardinals. However, the Red Sox defeated them in six games.

1. Rickey Henderson

The first-ballot Hall of Famer and baseball's all-time leader in runs and stolen bases took home the 1989 ALCS MVP Award. - Source: Imagn — The first-ballot Hall of Famer and baseball’s all-time leader in runs and stolen bases took home the 1989 ALCS MVP Award. – Source: Imagn

Rickey Henderson played for the Yankees from December 1984 to June 1989. He earned All-Star selections in his four complete seasons in the Bronx. However, the Yankees never reached the postseason during that span.

Henderson won the 1989 World Series with the Oakland Athletics, just months after the Yankees traded him. He racked up nine hits in four games as the Athletics swept the San Francisco Giants.

Henderson and the Athletics reached the 1990 World Series, but were swept by the Cincinnati Reds. He later won the 1993 World Series with the Toronto Blue Jays.

Edited by Joseph Schiefelbein

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