No other city has dominated this millennium in professional sports like Boston.
No other team has epitomized the extreme highs and dramatic lows of this sports community's last 25 years than the Red Sox. One curse broken. Three championships won. And more drama than any team in baseball. This club is chock full of "Where were you when ..." kind of tent posts. It's why revisiting this last quarter of a century is an exercise that will bubble up all sorts of emotions.
As 2025 draws to a close, WEEI.com ranks the 25 most significant moments for all four teams in town. That distinction of “significant” is key - not all moments of significance are covered in glory.
We had rankings for the Patriots on Monday and the Celtics on Tuesday. And after today's exploration into Red Sox memories, on Thursday, we'll bring you the Bruins' list.
With that said, here are your 25 most significant moments since 2000 for the Boston Red Sox:
25. 'Sweet Caroline' becomes the official anthem at Fenway Park (2002)
The song actually began being played in 1997 when Fenway employee Amy Tobey played the Neil Diamond masterpiece in tribute of a friend who had just given birth to a daughter named 'Caroline'. But it was five years later Red Sox marketing guru Dr. Charles Steinberg officially made it a staple for all Fenway games, bridging the top of the eighth inning to the bottom of the frame.
24. 2012 trade, sending Josh Beckett, Adrian Gonzalez, Carl Crawford and Nick Punto to the Dodgers (August 25, 2012)
With the Red Sox season well off the rails, and the stench of a history-making 2011 collapse sending the organization down a bad road, GM Ben Cherington swung a mammoth deal, clearing $250 million in payroll and helping set the stage for a world championship the next season.
23. 2011 collapse/fallout (September 28, 2011)
The Red Sox's walk-off loss to the Orioles on the final day of the season punctuated an unbelievable collapse, with Terry Francona's team blowing a nine-game lead on Sept. 2, a month that saw the Sox go 7-20 and lose 21 of their last 29 games. Then came the fallout, which included the departure of both Theo Epstein and Terry Francona, while bubbling up all kinds of unsavory stories and images involving the 2011 club.
22. Pedro Martinez's 2000 season
The campaign was one of the most dominant ever turned in by a starting pitcher, with Martinez going on to win his third American League Cy Young Award thanks to eye-popping statistics. There was a 17-4 record, 1.74 ERA, 284 strikeouts and just 128 hits and 32 walks allowed. The ERA champ was almost two runs better than the second-best mark of 3.70 owned by Roger Clemens.
21. Andrew Benintendi's catch in the 2018 ALCS (October 17, 2018)
Simply put, if Benintendi doesn't make his game-ending, diving catch on Alex Bregman's sinking liner in Game 4 of the 2018 American League Championship Series, the Red Sox don't win that game and maybe don't take the series (which means no World Series win). It was a catch with a 21 percent catch probability, which necessitated Benintendi needing to cover 45 feet in 3.2 seconds.
20. Trade for Chris Sale (December 6, 2016)
A few weeks before the momentous trade, Dave Dombrowski said he was going to flat-out deal for a ace. He found a really good one. The Red Sox cemented their spot among the American League heirarchy for the next few seasons thanks to the presence of Sale, who finished second in the AL Cy Young voting in his first year with the Sox. The price of giving up prospects Yoan Moncada, Michael Kopech, Luis Alexander Basabe and Victor Diaz was well worth it.
19. Drafting Mookie Betts (June 7, 2011)
With the 172nd pick in the 2011 MLB Draft the Boston Red Sox drafted a 160-pound kid from Tennessee named Markus Lynn Betts. After a few years dabbling as an undersized second baseman, Mookie took off, finding his way to the majors in 2014 on the way to launching what will be a Hall of Fame career.
18. The Jason Varitek/Alex Rodriguez fight (July 24, 2004)
This was the Red Sox/Yankees at its finest, with Rodriguez - the player the Red Sox tried to acquire a few months before - taking issue with a pitch from Bronson Arroyo before starting a back-and-forth with Varitek. Words built into pushing, shoving, and, ultimately, wrestling. It was the beginning of a back-and-forth between the teams that landed with the Red Sox's historic run through the World Series.
17. Josh Beckett's Game 5 performance the 2007 ALCS (October 18, 2007)
It was a season-saving eight innings. Beckett highlighted an unbelievable run through the 2007 postseason by outdueling eventual AL Cy Young winner CC Sabathia by giving up just one run in a win-or-go-home tilt in Cleveland. The Sox's win propelled them to come back from a 3-1 deficit in the best-of-seven series, leading to a sweep of the Rockies in the World Series.
16. The trade of Mookie Betts (February 4, 2020)
With Betts' contract set to expire after the 2020 season, and no agreement on a contract extension in sight, the Sox decided to deal their star outfielder to the Dodgers for Connor Wong, Alex Verdugo and Jeter Downs. Needless to say, it wasn't a good idea. Betts went on to sign a 12-year, $365 million extension, winning three World Series championships. It left the Red Sox spinning their wheels for much of next six seasons.
15. Aaron Boone's home run off Tim Wakefield (October 16, 2003)
The Red Sox were so close. But with one swing of the bat in the bottom of the 11th in Game 7 of the ALCS between the Sox and Yankees at Yankee Stadium, the curse dug its heels in. That was thanks to Aaron Boone's walk-off homer against Tim Wakefield. The Red Sox would need to wait one more year before showing the Yankees what was what.
14. The trade for Curt Schilling (November 28, 2003)
The Red Sox needed a bit of a push to get over the hump when it came to beating the Yankees and finally winning their first World Series since 1918. That's where Schilling came in. So for the price of Casey Fossum, Brandon Lyon, Jorge de la Rosa and Micahel Goss, the Sox secured one of the best big-game pitchers of all-time, a title he continued to earn while pitching in a Red Sox uniform.
13. The Alex Rodriguez trade falling apart (December, 2003)
This was going to be the Red Sox's answer to the Yankees' perceived dominance, getting one of the best players in baseball in a trade with the Texas Rangers. It would have cost the Sox Manny Ramirez, Jon Lester and cash. What might have been. The MLBPA blew up the deal because of the pay cut Rodriguez was being asked to take, leading the Yankees to step in and secure the services of the mercurial infielder.
12. The acquisition of David Ortiz (January 22, 2003)
It was considered a minor transaction, with the Red Sox taking a flier on a first baseman who the Twins had already released. But considering the deal would be for one year at just $1.25, the Sox had little to lose. After the agreement, all they did was win ... thanks to Ortiz. The lefty slugger finally cracked into the Sox's everyday lineup a few months into the 2003 season, launching a Hall of Fame career that included three world championships.
11. Jonathan Papelbon's final out of the 2007 championship season (October 28, 2007)
The Red Sox didn't have much practice celebrating World Series titles, with Keith Foulke's final pitch in 2004 as the only example. But Jonathan Papelbon did just fine. The Sox closer sealed the Sox's four-game sweep of the Rockies, immediately throwing his glove in the air, grabbing his head, and then jumping into the arms of catcher Jason Varitek. It showed the 2004 title wasn't a fluke in a powerful way.
10. Chris Sale's final out of the 2018 championship season (October 28, 2018)
Three World Series championships. Fifteen years before that would have seemed unthinkable. But when Sale got Manny Machado swinging to close out Game 5 of the 2018 World Series at Dodger Stadium, one of the best seasons of all-time was punctuated in style.
9. Koji Uehara's final out of the 2013 championship season (October 30, 2013)
Uehara hurdling himself into the arms of catcher David Ross was an iconic moment for so many reasons. For starters, it was the first time the Red Sox had clinched a World Series at Fenway Park since 1918. And secondly, it put the perfect bow on a championship season that paid homage to underdogs everywhere and to all those affected by the Boston Marathon bombings.
8. David Ortiz's grand slam in Game 2 of the 2013 ALCS (October 13, 2013)
It had to be a grand slam. Down 5-1 with two outs in the bottom of the eighth inning in Game 2 of a best-of-seven series against the Tigers painted an dreary picture for the Red Sox. A single, double or even triple, would have gotten things close, but still would have left the Sox in a hole. It had to be a grand slam or the Sox would have likely lost the game, and ventured to Detroit down 2-0. So, that's exactly what Ortiz did ... hit a grand slam. The slugger teed off on a Joaquin Benoit changeup and launched it just over the outstretched glove of Torii Hunter. An inning later, Jarrod Saltalamacchia would single in the game-winner, paving the way for the Sox's World Series run.
7. David Ortiz's walk-off single in Game 5 of the 2004 ALCS (October 18, 2004)
Speaking of season-saving walk-offs ... this one came in the form of Ortiz's 14th-inning single, scoring Jonny Damon to cut the Yankees' series lead to 3-2 and sending the teams back to New York.
6. David Ortiz's walk-off homer in Game 4 of the 2004 ALCS (October 17, 2004)
With the Red Sox trailing 3-0 in the best-of-seven ALCS against the Yankees in 2004, the teams found themselves in the 12th inning. It allowed for the first gigantic moment for Ortiz, who saved the Sox's season for the first time with a blast into the right field stands off Paul Quantrill, which kept the Red Sox's dim hopes still flickering.
5. Dave Roberts steal (October 17, 2004)
It's surreal to think about what would have happened if Dave Roberts had been thrown out trying to steal in the ninth inning of Game 4 in the 2004 ALCS. If he didn't make it, the rally by the Red Sox - who were down a run against Hall of Famer Mariano Rivera in the ninth inning - would have never happened, and there would be no Curse-breaking. But Roberts did make it, leading to Bill Mueller's game-tying single and the beginning of the most incredible comeback in MLB history.
4. Punctuating the comeback from a 3-0 hole in the 2004 ALCS (October 20, 2004)
Kevin Millar warned everyone before Game 4, with his team down 3-0 in the best-of-seven, not to let the Sox get hot. The Yankees did just that. Two wins at Fenway, followed by two more at Yankee Stadium and the Red Sox were owners of history. Of course, nobody could totally breathe easy until Pokey Reese scooped up that final out of Game 7 and flipped it over to first baseman Mientkiewicz to seal the deal.
3. The hiring of Theo Epstein (November 2002)
He was an innocuous local kid who was getting the chance to be a 27-year-old assistant GM for his hometown team. Then, after just one season, Epstein got the call to become the chief decision-maker for the Red Sox. From there, everything changed. While there are plenty of moments by plenty of players who helped the Red Sox go on their memorable run, it was Epstein who provided the foundation (and blueprint) to build the team that ultimately kicked the curse.
2. John Henry and Co. buying the Red Sox (December 20, 2001)
There have been plenty of slings and arrows thrown the way of this ownership group since it took over. But the scoreboard - which includes four world championships and a reinvigorated fan base - suggests it has won a whole lot more than it has lost, both on and off the field. The acquisition changed everything for the last 24 years.
1. Keith Foulke's final out of the 2004 championship season: Oct. 27, 2004.
Did we mention the Red Sox hadn't won a World Series since 1918?
