Yankees Have Long History of Red Sox Heartbreak to Overcome

That was 2003. It's 2025, and the Yankees haven't won a postseason series against Boston since.

The following year was that catastrophic 2004 collapse, where the Yankees blew a 3-0 lead in Alex Rodriguez's first season. It was revenge on multiple fronts. The stench of Boone's homer was wiped clean from the city of Boston, and a curse was reversed. Rodriguez, whose deal to Boston was nixed, watched from the other dugout as the Red Sox celebrated at Yankee Stadium after a miserable drubbing in game seven.

It wouldn't be until October 2018 that these teams would meet each other again in the postseason. That year, Boston made quick work of the Yankees. Gary Sanchez was poised to redeem himself after a tough season with a monster blast over the Green Monster, but his big at-bat against David Price was lost in the ether.

Boston handled the Yankees even faster in 2021, but that was by virtue of the one-game Wild Card. Gerrit Cole was dealing with a bum hamstring and got lit up at Fenway.

This week, we'll find out if these Yankees are any different than the previous ones. Despite going 4-9 against the Red Sox this season, they won their most recent series against them. This is not the first time they have achieved this, though, having also won the final Boston series in September 2018 and 2021. That did not happen in 2004, but blowing a 3-0 lead tops both as far as not capitalizing on a bit of momentum.

Just as it's a certainty for the New York Mets to collapse against the Miami Marlins in devastatingly spectacular fashion at least once a decade, things feel a little too serendipitous heading into this Wild Card series with the Red Sox.

George Bush Jr. was President the last time the Yankees beat Boston in October, but, for as long ago as that was, streaks are meant to be broken, and if there's one thing that this team has that the others didn't, it's a one-two punch of ace lefty gunslingers in Max Fried and Carlos Rodon. On paper, both can give the Yankees a strong six to seven innings.

Another thing the 2025 Yanks have is homefield advantage. They didn't have that in 2018 or 2021. The captain, Aaron Judge, mentioned that following their sweep of the Baltimore Orioles.

"We got a rowdy crowd out there, a rowdy group that's been there behind us all year long, even in our tough times in the summer," Judge said, according to Gary Phillips of the Daily News. "They're definitely going to be excited for a Yankees-Red Sox postseason matchup, that's for sure. So I'm expecting the stadium to be loud here on Tuesday."

Even with missing out on the division by a hair and finding himself in the Wild Card, Manager Aaron Boone is happy with where his team is. Especially compared to where they had been in August.

"A month and a half ago, we were teetering on, when it wasn't going great, even being out of the [playoff] picture a little bit," Boone said. "So to right the ship and then really solidify our position and then have a real shot at the East here all the way to the last day, hopefully it's something that serves us well, has kept us sharp, has kept us really locked in. I think that's a good thing."

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