Curse-breakers and superstars highlight MassLive Red Sox Quarter-Century Team

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Curse-breakers and superstars highlight MassLive Red Sox Quarter-Century Team

Chris Mason, Matt Vautour · MassLive

Mon, Dec 29, 2025 ·

10 min read

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The first 25 years of the 21st century were unbelievable for lifelong Red Sox fans. In 2000, the Curse of the Bambino was at 82 years and heartbreak was the norm.

Over the next quarter century, the Red Sox broke the curse in storybook fashion, winning it all in 2004 — and then added three more World Series rings to the collection in 2007, 2013, and 2018. Nobody has won more since 2000 than Fenway Park’s long-time lovable losers.

To commemorate the first 25 years, MassLive has elected a Red Sox Quarter-Century team of Boston ’s best of the best. There are only starters, no bench players — sorry, Dave Roberts — and then a full five-man rotation, setup man, and closer.

For this project, we invited our current Red Sox coverage team, as well as anyone who covered the Red Sox for MassLive and before that, the Springfield Republican, to vote.

So without further ado, let’s get to the Red Sox Quarter-Century team:

Note on methodology: Voters were instructed to only consider performance from 2000-25 and only what they did for the Red Sox. Outfielders could only be elected in their primary outfield spot.

Lineup

Catcher: Jason Varitek

Prior to breaking the curse, Red Sox captain Jason Varitek exchanged pleasantries with Alex Rodriguez (Jim Rogash/Getty Images)Getty Images

Years: 1997-2011

Championships: 2

Why he made it:A tone-setting captain, Varitek spent his entire career with the Red Sox and the team was better for it. Varitek caught four no-hitters, made three All-Star teams, backstopped two World Series championships, won one Gold Glove — and he hit Alex Rodriguez in the face with his catcher’s mitt. The face-full-of-glove photograph will live on in Boston sports bars for generations.

Also receiving votes: None.

First Base: Kevin Youkilis

Years:2004-2012

Championships: 2

Why he made it:Youkilis was a Boston dirt dog who mastered both corner infield spots, but won a Gold Glove at first base. A three-time All-Star, Youkilis was famously dubbed “The Greek God of Walks” in “Moneyball,” but carved out a career doing far more than that in Boston. On the playoff run that culminated in the 2007 World Series, Youkilis hit .388 with 4 home runs 10 RBIs, and an OPS of 1.230.

Also receiving votes: None.

Second Base: Dustin Pedroia

Years: 2006-2019

Championships:3

Why he made it: Generously listed at 5-foot-9, Pedroia squeezed out every ounce of talent he possibly could have and let everybody know it. A baseball rat, Pedroia won the American League Rookie of the Year and MVP in back-to-back seasons, as well as four Gold Gloves and a Silver Slugger at second base. Pedroia’s “laser show” career was on a Hall of Fame trajectory until it was derailed by a Manny Machado slide.

Also receiving votes: None.

Third Base: Rafael Devers

Years: 2017-2025

Championships:1

Why he made it: A three-time All Star, Devers garnered MVP votes in five different seasons as a member of the Red Sox. The slugging third baseman hit 215 homers in 1053 games with Boston and added 273 doubles. His falling out with the front office and subsequent trade to the Giants was a shocker, but Devers’ production at the plate dwarfed any other Sox third basemen from the 21st century.

Also receiving votes: None.

Shortstop: Xander Bogaerts

Years: 2013-2022

Championships:2

Why he made it: A homegrown success story, Bogaerts spent his first 10 seasons with the Red Sox, winning a pair of World Series rings. The sure-handed shortstop won a pair of Silver Sluggers, was voted to four All-Star games, and garnered MVP votes in five seasons. No other Red Sox shortstop comes close to matching his accomplishments over the past 25 years.

Also receiving votes: None.

Left field: Manny Ramirez

Terry Francona chats with Manny Ramirez (Photo by G Fiume/Getty Images)Getty Images

Years:2000-2008

Championships: 2

Why he made it: One of the sweetest right-handed swings to grace Fenway Park, Manny was in Manny’s world sometimes, but at the plate he could still absolutely rake. During his eight seasons with the Sox, Ramirez hit .312 with 274 home runs, 868 RBIs and a .999 OPS. He went to the All-Star Game every season with Boston, finished Top 10 in MVP voting five times, and would be a Hall of Famer if not for positive tests for performance-enhancing drugs.

Also receiving votes: None.

Center field: Johnny Damon

Years:2002-2005

Championships: 1

Why he made it: A cult hero during his time in Boston, the long-haired, bearded center fielder was a quintessential piece of the 2004 team that reversed the curse. Damon made a pair of All-Star Games during his four seasons in Boston and crushed the Yankees in Game 7 of the 2004 ALCS, hammering a grand slam and driving in six runs in the 10-3 clincher.

Also receiving votes: Jacoby Ellsbury

Right field: Mookie Betts

Years: 2014-2019

Championships: 1

Why he made it: There may never be another trade as bad as Babe Ruth’s, but as far as 21st-century deals go, Mookie Betts is up there. A homegrown superstar, Betts was traded to the Dodgers amidst perception by the team that they couldn’t re-sign him. During his six seasons in Boston, Betts won four Gold Gloves, three Silver Sluggers, an AL MVP and a World Series. Not bad for a guy who had just turned 27 when he was traded.

Also receiving votes: None.

Designated Hitter: David Ortiz

Years: 2003-2016

Championships:3

Why he made it:The face of Boston’s turnaround. After 86 years of the franchise crumbling in big moments, Ortiz thrived in the clutch. Whether it was his three walk-off hits in the 2004 postseason — two of which came when facing elimination in the ALCS — or batting .688 in the 2013 World Series, the 6-foot-3 slugger felt even bigger when the lights were brightest. He made 10 All-Star Games and hit 483 home runs with the Red Sox, paving a path to Cooperstown. Boston was his (bleeping) city.

Also receiving votes: None.

Pitchers

Starter: Pedro Martinez

Red Sox ace Pedro Martinez was still dominant at the height of baseball's Steroid Era (Photo by Don Smith/MLB Photos via Getty Images) MLB Photos via Getty Images

Years:1998-2004

Championships: 1

Why he made it: The most dominant pitcher of his era, Martinez was in his prime at the turn of the century. Though only 170 pounds, the Dominican right-hander owned the inside of the plate. As he won the AL Cy Young Award in 2000, Martinez went 18-6 with a 1.74 ERA and 0.737 WHIP, striking out 284. Those numbers are even more eye-popping in the height of the steroid era.

Starter: Jon Lester

Years:2006-2014

Championships: 2

Why he made it: A harbinger of more mismanaged homegrown stars to come, Lester was an integral part of two World Series victories in Boston. The cancer-surviving lefty was nails in the playoffs, posting a 2.11 ERA in 13 appearances with the Red Sox, and he won 110 regular-season games in Boston. A lowball offer from ownership ahead of free agency led to a trade to Oakland, and after a layover with the A’s, Lester found a second home in Chicago and helped the Cubs break their own World Series curse.

Starter: Josh Beckett

Years: 2007-2012

Championships: 1

Why he made it: It was a rollercoaster run for Beckett in Boston, but the highs were undeniable. The AL Cy Young runner-up in 2007, Beckett was an ace, going 20-7 with a 3.27 ERA. Then he found another level in the postseason, where he went 4-0 with a 1.20 ERA and 0.700 WHIP en route to the World Series. The chicken and beer debacle of 2011 ultimately led to an ugly divorce, but Beckett at his best was outstanding.

Starter: Curt Schilling

Curt Schilling's famous bloody sock. (AP Photo/Charles Krupa)

Years: 2004-2007

Championships:2

Why he made it: With a bloody sock that will live forever in Red Sox lore, Schilling was instrumental in breaking the Curse of the Bambino as well as bringing a second championship to Boston in 2007. A prototypical big game pitcher, Schilling went 6-1 with a 3.28 ERA in eight postseason starts. During the 2004 run Schilling was a much-needed veteran presence that had won before and wasn’t shaken by ghosts of the past. He also finished second in the AL Cy Young voting that year, going 21-6.

Starter: Chris Sale

Years: 2017-23

Championships:1

Why he made it: Things didn’t end well for Sale in Boston, but the early years could be lights out. An All-Star in his first two Red Sox seasons, Sale finished second and fourth in Cy Young voting, respectively. His strikeout of Manny Machado to end the 2018 World Series is a photo that will live in Boston barrooms for ages. Durability and injury were issues for Sale, but when he was right, his stuff was nasty.

Also receiving votes: Tim Wakefield, Derek Lowe

Setup man: Hideki Okajima

Years: 2007-2011

Championships:1

Why he made it: There were quite a few candidates here, but Okajima rose to the top of the pack thanks to a strong three-season run from 2007-09. An established Japanese pitcher, Okajima came to MLB at 31 years old and emerged as a key piece during Boston’s run to the 2007 World Series championship. The setup man for Jonathan Papelbon earned an All-Star berth that season and posted a 2.11 ERA with a 0.844 WHIP in three postseasons with Boston.

Also receiving votes: Mike Timlin

Closer: Jonathan Papelbon

Red Sox closer Jonathan Papelbon didn't shy away from cebrating (AP Photo/Winslow Townson)AP

Years:2005-2011

Championships:1

Why he made it:One of the best closers in the game with Boston, Papelbon was a four-time All-Star who became a household name with his “Shipping Up To Boston” entrance and river dancing celebrations. Work hard, play hard. Papelbon posted a 2.33 ERA as he racked up 219 saves with the Red Sox and didn’t allow a single run in the 2007 postseason.

Also receiving votes: None.

Manager: Terry Francona

Years: 2004-2011

Championships: 2

Why he made it: The perfect manager for the curse-breaking 2004 Red Sox, Francona knew how to navigate a clubhouse with plenty of big personalities (Pedro Martinez, Manny Ramirez, Curt Schilling, David Ortiz, etc.) and was a strong in-game manager as well. Francona’s 744 wins are the second most in franchise history — trailing only Joe Cronin (1071) — and he’ll certainly find his way to Cooperstown when all is said and done.

Also receiving votes: None.

General Manager: Theo Epstein

Years: 2002-2011

Championships:2

Why he made it:One of the best executives in baseball history, Epstein blended old-school ideas with new-age information to break an 86-year curse. He was fearless enough to deal face-of-the-franchise Nomar Garciaparra in 2004, and his signing of David Ortiz and trade for Curt Schilling helped put Boston over the top.

Also receiving votes: None.

Voters:

For this project, we invited our current Red Sox coverage team, as well as anyone who covered the Red Sox for MassLive and, before that, the Springfield Republican, to vote.

This team was selected by: Sean McAdam, Chris Cotillo, Chris Smith, Jim Pignatiello, Ron Chimelis, Chris Mason and Matt Vautour.

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