The Red Sox And Yankees Are Set To Meet In the Playoffs And All The Pressure Is All On New York

Jim Rogash. Getty Images.

I heard a Red Sox executive say last week that the most intense atmosphere he'd ever experienced at Fenway Park  - over decades of being around the team - was the Red Sox 6-2 win over the Yankees in the one-game Wild Card Playoff back in 2021.

Fast forward to 2025 and a now best-of-three Wild Card round - and I expect the intensity will be just as high this week at Yankee Stadium for the Red Sox and Yankees.

And all the pressure is on the Yankees to win and advance. 

Just look at how some of the biggest Yankee fans at Barstool are reacting. 

Tommy is not scared of eating weird bugs on an island to win Survivor, but he's afraid of Garrett Crochet. And he should be. Chrochet was 3-0 in four starts against the Yankees this season. In his seven career games against NY, he has a 2.90 ERA and has held NY bats to a .195 batting average. On extended rest, Crochet has a career ERA of 2.03. He'll get the ball in Game One on Tuesday. 

I can actually feel Hubbs shaking in his fancy Papasan chair as he posts this. He edited that at least seven times before posting it. There is no chance he wanted to see his Yankees face Boston this week. 

Marty seems like the one guy crazy enough to be okay with the Yankees catching the Red Sox in the Wild Card round. That kind of brash confidence helped him score 718 points in the first KMS/Barstool NY Basketball Game. Marty was like Steph Curry in that game. 

But these guys know - ALL the pressure is on NY to win this series. They finished five games ahead of the Red Sox in the standings. They're at home. They have Aaron Judge. They're favored. The Yankees are SUPPOSED to win. 

But the Sox have Crochet. And Alex Bregman. Boston won eight of the first nine games against NY this year, going 9-4 overall and 5-2 at Yankee Stadium. They have a better manager. They get to play the role of spoiler; it always comes with less pressure. 

If the Red Sox lose, it will still be a successful season. 

If the Yankees lose, their season will be a failure. 

And then there's this - the last three times the Red Sox and Yankees have met in the playoffs, the Sox ended the Yankees' season. 

2004. 2018. 2021. 

You can feel that looming over Hubbs' post. 

Yankees fans will pretend they're okay with the Sox matchup, but they're lying. They know the Sox have had their number this season and in recent playoff series, and would have much rather faced anyone else. 

I'm on record - I was hoping the Sox would get the Jays in the Wild Card. I felt like that was the best path to the ALDS. 

But seeing this reaction from the Barstool Yankee Fandom fires me up - you can sense the fear in the fanbase. All the pressure is on New York - and they know it. 

Red Sox/Yankees Wild Card Schedule 

Game 1 at New York: Tuesday, Sept. 30 at 6:08 p.m. ET 

Game 2 at New York: Wednesday, Oct. 1 at 6:08 p.m. ET 

Game 3 at New York: Thursday, Oct. 2 at 6:08 p.m. ET (if necessary)