NEW YORK — There’s close to 125 years of history when the Red Sox and Yankees meet, and especially when it’s October, the old, yellowed, crumbling pages somehow become crisp and relevant again.
That part is largely the romantic notions of fans, writers and influencers, especially in Connecticut, a not-so-demilitarized zone that sits between them on the map. The players who will compete at Yankee Stadium in the three-game wild card series beginning Tuesday are barely old enough to remember even the more recent epic struggles. They will, nevertheless, have the pens in their hands to write the next verse in this never-ending story.
“It’s Red Sox-Yankees, it gets your attention,” Yankees manager Aaron Boone said. “I’d throw it in there with the best rivalries in all of sports.”
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Boone found the pen in his hand on an October night across the street in 2003, and he hit Tim Wakefield’s knuckleball into the left field stands at the old Stadium to lift the Yankees into that World Series. History has proven that moment to be the height of frustration for the Red Sox, who hadn’t won the World Series in 85 years, and the last gasp of Yankees dominance. The Red Sox erased a 3-0 deficit, unheard of before or since, to eliminate the Yankees and take it all in 2004, and have since ended the New York seasons in Octobers of 2018 and ’21, by which time Boone was managing on the wrong side.
This is a rivalry created to break hearts and there are plenty on both sides, shattered and strewn across the decades. None of that means a thing this week, not until something happens that reminds everyone of something that happened 20 or 40 or 50 years ago.
You’ll be hearing about those things as if they are part of the proceedings, about Jack Chesbro’s wild pitch, Bucky Dent’s home run and Dave Roberts’ stolen base. And you will be hearing about the Yankees’ 4-9 record against the Red Sox this season, and their generally lackluster performances against the better teams across 2025. Is that more or less relevant than their 34-14 record to finish out the season at 94-68?
Much will be made of Aaron Judge’s latest monster season in New York, the first time since 1956 a player won the batting title and hit more than 50 home runs, juxtaposed against his inability to produce big moments in the postseason. That the Yankees have not won a championship since 2009 is a burden largely worn by Judge and Boone.
All these things past and present will unfurl beginning Tuesday at 6:05 at Yankee Stadium, but at the outset the pens to begin writing this chapter are in two formidable left hands. One belongs to Max Fried, who became a Yankee because Juan Soto left $750 million behind and joined the Mets last winter, and became their ace when Gerrit Cole’s elbow gave out in the spring. The other hand is the Red Sox’s Garrett Crochet, rescued from the abysmal White Sox in the most fruitful of several trades engineered by GM Craig Breslow, the Trumbull High and Yale alum.
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Legendary pitchers, Hall of Famers, have worked the big room for the Yankees and Red Sox, but rarely, if ever, have two aces at the zenith of their careers clashed in such a high-stakes game. Fried (19-5) led the majors in wins, Crochet (18-5) led in strikeouts with 255.
Crochet, 26, has no memories of watching Yankees-Red Sox other than “The Comeback,” the Netflix documentary on 2004. “I wish I had a better answer for you,” he said.
Fried, 31, is old enough to remember his manager’s moment. “The first memory I have, ironically enough, is Aaron Boone’s home run,” he said. “If you asked me then, I probably wouldn’t have thought I’d ever be a part of this, but I’m glad I am now.”
Formats change, each circumstance unique. The Red Sox and Yankees have played winner-take-all regular season finales in 1904 and ’49, a one-game playoff, technically a 163rd regular-season game in 1978, and in the wild card era, playoff series in 1999, 2003, 2004 and 2018 and the one-game wild card elimination game in 2021. Red Sox manager Alex Cora, who led them to the championship in ’18, brought up Xander Bogaert’s home run off Cole in that 2021 game.
“Xander’s homer in ’21, that was the loudest I’ve ever heard Fenway Park,” Cora said “That was electric. The ball went out and the place went nuts, that’s the one that gets my attention.”
After three sub-par seasons, the Red Sox (89-73) returned to the playoffs as a wild-card entry, playing consistently well from June on. Alex Bregman, that old Yankees nemesis from Houston, will take 100 games of postseason experience into Tuesday night’s game, leading Cora’s righthanded lineup against the lanky Fried and his expansive repertoire.
“Alex (Cora) has been trying to play the ‘Little Engine That Could,’” Boone said. “But a lot of people knew the Red Sox were coming this year.”
Boone will stack righthanded hitters against Crochet, who was 3-0 with 39 strikeouts in 27 1/3 innings against the Yankees. That means Ben Rice, the rising Yankees star, who hit 25 home runs, probably won’t start, but you’ll hear about him. He’s the kid from Boston who somehow made it to adulthood as a Yankees fan, claiming he scribbled “Yankees Rule” on Fenway Park’s Pesky Pole. Good chance photos of him as a toddler in head-to-toe Yankees gear will make it onto your TV screen a time or two.
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History and childhood dreams always make great narratives. Crochet, though he is fairly young and new to the Red Sox, overruled his manager’s dress-down order and urged his teammates to wear business casual for their travel from Boston to New York. The 6-foot-6 lefty is all business, all here and now. Maybe that’s the way to handle all of this.
“This could be a once-in-a-lifetime opportunity for some guys on this team,” Crochet said. “I think we should treat it with the dignity it deserves.”
The stakes could only be higher in an elimination game; the loser of Game 1 will have spent its ace and face elimination Wednesday. The Red Sox’s veteran No. 3 starter, Lucas Giolito, is out with an elbow injury, so if the series goes to Thursday percentages tilt toward New York — depending on who next has the pen in his hand. Rookie sensation Cam Schlittler, a Bostonian who grew up a Red Sox fan, would pitch that one in pinstripes.
“What you see is what you get, two stories franchises going head to head,” said Fried, who calls upon World Series winning experience with the Braves. “This is its own game, new thing, new season, new circumstances. … Anyone can be the hero at any moment.”