Sports

9 Most Hated Players in the Red Sox-Yankees Rivalry

By Zach Kaplan Athlon Sports

Updated June 9, 2026 2:22 PM

At the core of the rivalry between the New York Yankees and Boston Red Sox are countless personalities who have mixed like oil and water.

In this article, we've set out to name the most hated players in the history of baseball's most famous matchup.

It's tough to narrow it to just a few -- can we mention former Red Sox owner Harry Frazee for selling Babe Ruth and kicking off the Curse of the Bambino? How about Ruth himself? -- but here are a few honorable mentions before getting to the bones of the rivalry.

Honorable Mentions

Johnny Damon, Yankees/Red Sox: Damon was initially hated by Yankees fans for being an integral part of Boston's 2004 World Series team that broke the Curse of the Bambino, but decided to jump ship and leave Boston for New York just one year later.
Manny Ramirez, Red Sox: Ramirez grew up in the Bronx, playing baseball just miles from Yankee Stadium, and instead of joining the Yankees, he wound up punishing their pitching, especially during the 2003 ALCS. Ramirez always said he wanted to be a Yankee as he grew up a fan of the team.
Jason Varitek, Red Sox: Boston's beloved catcher and longtime captain etched his place into Yankee infamy in July 2004 when he shoved his glove into Alex Rodriguez's face, sparking a benches-clearing brawl.

MORE: Top 5 Moments That Defined the Red Sox-Yankees Rivalry

Biggest Yankees Villains

Alex Rodriguez

Rodriguez is one of the most hated players in baseball history, really. His intense, flashy style didn't sit well with many, and his 2014 PED suspension led to a host of resentment over the way the star third baseman played the game.

That resentment very much extended to Boston. Following the Red Sox demoralizing ALCS loss to the Yankees, the Rangers had agreed on a trade in the 2003 offseason to send Rodriguez to the Red Sox in exchange for Ramirez and Jon Lester, but the trade was vetoed by the MLB Players Association due to the pay cut Rodriguez agreed to as part of the deal.

Months later, "A-Rod" was traded to the Yankees, and he brought his fiery style of play to every game of the rivalry. In his first year with the Yankees, A-Rod was involved in two major altercations with Red Sox pitcher Bronson Arroyo.

The first came on July 24, when Arroyo hit Rodriguez with a pitch, and Rodriguez exchanged words with the pitcher before Red Sox catcher Jason Varitek stuck his glove in Rodriguez's face, leading to an on-field brawl.

Evidently, the tensions hadn't simmered down by the time the 2004 ALCS came around, as Rodriguez hit a ground ball back to Arroyo in Game 6, and slapped the ball out of Arroyo's glove as he tried to tag him out. A-Rod was ruled out for intentional interference and Derek Jeter was sent back to first base, nullifying a Yankees run.

Both of these incidents and the near-Red Sox trade make A-Rod an all-time hated player in this rivalry.

Bucky Dent

Dent was hardly hated by Red Sox fans before October 2, 1978, but from then on, was only known as "Bucky F-ing Dent."

The Yankees shortstop, who hadn't been known to hit for power and only hit 40 home runs in his 12-year career, stepped up in the seventh inning of the Yankees-Red Sox AL East division tiebreaker game at Fenway, with the two teams each possessing an identical 99-63 record.

Dent proceeded to club a three-run home run over the Green Monster to give the Yankees a 3-2 lead that they wouldn't lose; the Yankees would go on to win the World Series over the Dodgers and the Red Sox, as a consequence of losing the game, would miss the playoffs entirely.

Roger Clemens

Clemens could technically be classified as both a Yankee and Red Sox villain, depending on the day. "The Rocket" spent his early prime in Boston from 1984 to 1996, winning three Cy Young awards along the way, but was offered a lackluster contract following a frustrating 1996 season.

After then-Red Sox GM Dan Duquette said Clemens was "in the twilight of his career," Clemens left for the Toronto Blue Jays, insulted, and won back-to-back Cy Young awards in his two seasons up north. Following his dominance, Clemens forced a trade to the arch-rival Yankees.

While with the Yankees from 1999 to 2003, Clemens tormented the Red Sox, the team that drafted him in the first round. Clemens was a fixture of the Yankees teams that won back to back titles in 1999 and 2000, and won another Cy Young award in 2001.

Clemens was also an indirect part of the huge brawl between Pedro Martinez and Yankees bench coach Don Zimmer (more on that below).

Clemens' later years were mired in steroid allegations, which were the final icing on the cake to him being quite detested by Red Sox fans.

Biggest Red Sox Villains

Pedro Martinez

The reason Martinez is so hated by Yankee fans goes way beyond his dominance with the Red Sox, and his incredible, Cy Young award-winning 1999 and 2000 seasons.

Martinez was the face of one of the most infamous brawls of all time between the Yankees, as after Clemens threw near a few Red Sox batters in the 2003 ALCS, Martinez felt the need to throw a ball over the head of Yankees batter Karim Garcia, leading to an all-out brawl that ended with Martinez shoving 72-year-old Yankees bench coach Don Zimmer to the ground.

While Martinez and Zimmer both expressed remorse for the brawl, that moment will forever live in the heads of Yankees fans who saw the tensions bubble up and boil over in the early 2000s.

David Ortiz

"Big Papi" is one of the great personalities in baseball; he's also the greatest Yankee killer of all time.

Ortiz turned his game up a few notches each time he played the Yankees, beginning notably with his role in helping the Red Sox claw their way back from a 3-0 deficit in the 2004 ALCS with a 12th-inning walk-off home run in Game 4 and a 14th-inning walk-off single the next night.

Ortiz would continue the trend with a first-inning home run in Game 7 at Yankee Stadium; the Red Sox remain the only team to claw back from a 3-0 deficit to win a series, and Ortiz was right in the middle of it.

From 2004 up until his game winning home run off Dellin Betances in his final rivalry season in 2016, Ortiz tormented the Yankees endlessly.

While the Yankees honored Ortiz with a pregame ceremony during his last trip to the Bronx in 2016, Ortiz continues to lean into his role as the top Red Sox villain as a postgame analyst on FOX, where his line of "Daaaa Yankees Lose" just rubs salt into an open wound.

Curt Schilling

Schilling will always be one of the players hated most by Yankee fans, but not just for his time with Boston. Schilling pitched for the Arizona Diamondbacks in 2001 and was a big part of Arizona's surprising World Series win over the Yankees, who had won three consecutive World Series to that point.

Schilling was named co-MVP of the World Series alongside Randy Johnson after giving up just three runs over 21 1/3 innings in Games 1, 4, and 7.

When Schilling came over to Boston after the 2003 season, the Yankees had a prime opportunity to get revenge on the man who had almost singlehandedly spoiled their four-peat ambitions.

That didn't happen, and in fact, Schilling was one of the main contributors who helped the Red Sox win the 2004 ALCS. After suffering a torn tendon sheath in his ankle in the ALDS, Schilling received a temporary suturing procedure from a surgeon to be able to pitch in the ALCS.

Schilling toed the slab in Game 6 at Yankee Stadium, the Sox still trailing 3-2, with a completely bloody sock, and pitched seven innings with just one run allowed. Schilling's excellent performance set the table for a 4-2 Red Sox win to even the series at 3-3, where they would punish the Yankees in Game 7 for leaving the door open with a 10-3 shellacking.

Schilling's time with the D-Backs, and his gritty performance against the Yankees in the ALCS will always leave his legacy infamous in New York.

This story was originally published June 9, 2026 at 2:08 PM.