Rivalry Renewed

By: Chris Felico

For nearly half a decade, the most historic rivalry in baseball has been more of a side note than the centerpiece of the sport. The Boston Red Sox and New York Yankees, two franchises built on generations of bad blood, have not crossed paths in the postseason since 2021. While the Yankees remained contenders, even reaching last year’s World Series before falling to the Los Angeles Dodgers, Boston struggled to regain its footing. The only real satisfaction Sox fans could cling to during this drought was their team’s uncanny ability to beat the Yankees in the regular season, despite finishing outside the playoff picture for five consecutive years. But now, the script has flipped — October has arrived, and the Red Sox and Yankees are set to meet again when it matters most.

The 2025 Wild Card Series has all the makings of a classic. In Game One, the Red Sox will send breakout ace Garrett Crochet to the mound against New York’s prized offseason acquisition, Max Fried. It’s a heavyweight battle that will set the tone for the series inside Yankee Stadium. Game Two is no less compelling, as Boston’s homegrown star Brayan Bello takes on veteran left-hander Carlos Rodón. Should the series extend to a winner-take-all Game Three, the Red Sox may turn to a bullpen-heavy strategy or roll the dice with one of their promising young arms. On paper, it’s a matchup of stability versus uncertainty, but as history has shown, anything can happen when these two teams collide in October.

Boston enters this matchup with confidence after dominating the Yankees throughout the regular season. The Red Sox claimed series after series against their rivals, with their only stumble coming in the final meeting of the year this past September. Still, the postseason is a different animal, and both sides know that regular-season success means nothing once October begins. For the Red Sox, the challenge is proving they can carry that same edge into Yankee Stadium under the brightest lights, while the Yankees look to flip the narrative and show why they remain perennial contenders.

The emotions surrounding this series are as high as they’ve been in years. For Boston, it’s excitement tempered with nerves. This young Red Sox team has talent, but very little playoff experience, and playing in the Bronx is as intimidating as it gets. For New York, the pressure is just as intense. Fresh off a World Series appearance, the Yankees are expected to take care of business, but the weight of expectation can be its own challenge. Both fan bases know the stakes — bragging rights, legacies, and the chance to derail a rival’s season all hang in the balance.

No one knows how the 2025 Wild Card Series will end, but one thing is certain: the rivalry has been reignited. With Boston’s youth going toe-to-toe against New York’s seasoned roster, the stage is set for another unforgettable chapter in this timeless feud. No matter which team advances, this postseason battle ensures that the Red Sox–Yankees rivalry won’t just be a memory of the past — it’s alive and thriving, with the promise of more to come in the years ahead.