Yankees Vs. Red Sox Greatest Rivalry in Sports…Now, Conclusion: How October's Been A Very Different Month Since 2004

 

In retrospect the Yankees winning the American League Pennant over the Red Sox in 2003 was the last gasp of what has been the last great baseball dynasty to this point. The Yankees of Jeter-Posada-Williams and so forth had managed to win six pennants and four World Series between 1996-2003. It remains one of the great accomplishments in baseball history, made all the more glorious that it would take until 2025 for another team – the LA Dodgers to win back-to-back World Championships. As we all saw this past week when the Brewers swept LA in four games in the NLCS, it has become all the harder to even come close to a three-peat in baseball.

The Yankees have always been a perennial contender during the 21^st century. They've won 9 American League East Division titles between 2004 and 2024 and have made the MLB playoffs every single year since 2017. But the last time they won the World Series was in 2009 and it wasn't until 2024 that they made it to the World Series again, albeit to be swept by the Dodgers in five games. And they've only made it to the second round of the baseball postseason four times besides this, losing three times to the Houston Astros. (And no there comes a point when you can't blame this entirely on their management: the Astros swept them in 2022.)

Boston has by contrast enjoyed far more success ever since the 2004 World Series having made the American League playoffs ten times since 2004. They've won three World Series since then, sweeping Colorado in 2007, beating the Cardinals in six games in 2013 and trouncing the Dodgers in five games in 2018. They haven't made it back to the World Series since then but that's more a nature of how baseball is radically different. The four World Series they've won are more then any other franchise has managed to do in the 21^st century, which represents more of the era in which we live.

The Red Sox's triumph in 2004 officially ushered in an era where championship droughts that took up decades, even over a century, came to an end. In 2005 the Chicago White Sox, whose last World Championship had been in 1917 and whose last World Series appearance had been in 1959, would sweep the Houston Astros (then in the National League) to end their eighty-eight year drought. In 2010 the San Francisco Giant, who hadn't won a single World Series since they'd moved their from New York in 1958 won their first World Series and would then have the closest thing to a dynasty we've seen since then, winning three World Series in five years.

In 2014 they'd managed to defeat the Kansas City Royals, who had not been to the World Series since 1985 when they'd won the franchises first World Series in an epic seven game battle. The following year the Royals returned to the World Series and would defeat the Mets in five games.

That year the Chicago Cubs won their first postseason series since the disaster that had been 2003 defeating the St. Louis Cardinals. However they would lose to the Mets who managed to get back to the World Series for the first time in 15 years. But the following year the Cubs broke the longest drought winning the NLCS. And in an epic postseason battle they came from behind to defeat the Cleveland Indians to win their first World Series in 108 years.

Other franchises that had existed for over half a century and had never won a World Series reversed their fortune. The Houston Astros have been one of the most controversial teams in baseball since they switched from the National League to the American League. But after defeating the Dodgers in 2017 in a controversial World Series they would defeat the Phillies in the 2022 World Series by a margin of 4 games to 2. In 2019 they would face off against the Washington Nationals in what was the first World Series for DC since the Senators had won the American League Pennant in 1939. The Nationals managed an epic seven game victory to give Washington its first World Championship since 1924 when Calvin Coolidge was in the White House.  A former Senators team – the Texas Rangers – had never won a World Series despite making it in back to back appearances in 2010 and 2011. In 2023 they won the first World Series in the franchises history, dating back to 1961.

During the last decade the most perennial contender in baseball have been the Los Angeles Dodgers. They have come closest of all the teams in baseball to having a dynasty, winning three pennants between 2017 and 2020 and back to back ones in 2024 and 2025. But it still took them 32 years to manage to break the drought that had plagued them since 1988's surprise upset – and it wasn't lost on them that they won under the conditions of a very shortened and Covid driven season in 2020.

Far more frequently in 21^st century baseball have smaller market teams have been managing to make it further in the postseason then they ever had a chance to do in the 'good old days' when there was no wild card and only two divisions in each league. This Friday we will see the ultimate realization of that as the Tampa Bay Rays will face off against the Milwaukee Brewers. The Rays have existed since 1998, the Brewers since 1970 and neither team has ever won a World Championship. The last time this ever happened in the World Series was in 1980 when the Philadelphia Phillies and the Kansas City Royals were battling and the Phillies won the first World Series in franchise history.

While some small market teams are still struggling to make it back to the World Series – the Pirates, the Reds and the now homeless A's are currently among the teams with the longest droughts -  it's hard to argue that the extended baseball postseason hasn't given a chance for expansion and smaller teams to get closer to the World Series then they ever had before. The Rays are the best current example of this, but the White Sox managed to win their first postseason series this year after three consecutive seasons of 100 losses or more, something unprecedented in baseball history. And its done wonders for some franchises who were known as perennial losers. The Phillies managed to win three pennants and a world series during the 22 years of the 21^st century which is nearly as many as they won during the entire 20^th. They've also made the postseason five consecutive years after not getting close to it since 2011. And the St. Louis Cardinals have continued to thrive, having won four NL Pennants and two World Series (neither against the Red Sox, of course, and remaining until recently, one of the most consistently winning teams in baseball. They thrive under any system.

As for the Yankees and Red Sox their rivalry has now taken an added turn as they fight in what is very well the most talented division in all of baseball: the American League East. The more the wild card race is expanded the longer it takes to settle which teams in it won't be getting into the postseason and the battles between them take on an added fervor that never goes away. It is not lost on the fan that the Rays have become just as much a force in baseball as the Yankees these days and that all the other teams are just as sharp.  The Orioles have been contending in 2023 and 2024, the Blue Jays made it last year.

So when the Red Sox in the postseason it’s a battle that counts and so far, it's dead even. In 2021 the Red Sox beat the Yankees in the AL Wild Card Game 6-2 before losing to the Rays. In 2025 the Yankees beat the Red Sox in a best of three game playoffs but were then beaten by the Blue Jays. And this past year the Yankees swept the Red Sox in what was a dominant postseason but were in turn swept by Tampa Bay.

So 25 years into the 21^st century the Red Sox-Yankees rivalry is on even terms at last. It is now in truth what in the 20^th century it was only in name: the greatest rivalry in baseball. That being said I'm going to be pulling for the Brewers in this series. When you haven't won a World Series since Eisenhower's second term and your only other appearance in one took place before Reagan's first midterms, well, it really does make the Yankees 'championship drought' look mild by comparison.

Besides, I'm still from a Yankee household. If I rooted for Tampa I might very well be disowned.