In 2025, Yankees seek Red Sox postseason redemption

The New York Yankees face their blood rival Boston Red Sox in the AL Wild Card round this year and, though Derek Jeter won’t like how we put this, the series isn’t simply about winning and advancing.

Rather, this Yankees-Red sox best-of-three series is a test in baseball redemption. And not just because the Red Sox trounced the Yankees in the season series, 9-4. That’s meaningless. New York was 4-8 against Boston in 1999 and still dispatched them in five games in the 1999 ALCS en route to a second consecutive World Series title.

Instead, this playoff series is about one thing: the Yankees proving they can still beat Boston in October.

It’s easy to forget that, since the infamous Choke Job of 2004, the Yankees have faced the Red Sox in the postseason not once, but twice. Both times, the Bronx Bombers lost out badly.

The first time, in 2018, we should give the Yankees some grace. Not only was it Aaron Boone’s first year succeeding Joe Girardi after run to Game 7 of the ALCS a year prior, but New York won 100 games and Boston was just stupid good that year. The Sawx won 108 games, sign-stealing scandal or none, and the talent gap showed in the ALDS.

Lefty ace Chris Sale shut the Yankees down in Game 1 before an Aaron Judge homer and strong start from Masahiro Tanaka in Game 2 provided some false hope. Luis Severino tipped pitches and was rocked in Game 3’s 16-1 loss, and Boston got some help from Angel Hernandez in a tight Game 4.

The 2021 single-elimination Wild Card at Fenway was no better. New York stumbled into the playoffs that season despite 92 wins. Boston got to ace Gerrit Cole early in a one-sided 6-2 victory. All the more bittersweet, this also proved to be fan favorite Brett Gardner’s last game.

So, what went wrong for the Yankees against Boston in 2025? What was it about their hated rival Red Sox that made them so difficult a matchup this year? Was somebody hurt? Did drama behind the scenes affect the team?

Well, as is often the case in baseball, the reason the Yankees didn’t perform well against the Red Sox is simply that: Baseball. Every 162-game season is a bell curve. On one end is where everything goes according to plan, and Murphy’s Law on the other. Every season, most if not all teams fall somewhere in the middle. Billions upon billions of potential outcomes.

In the Yankees’ case this season, their playing their worst baseball of the year just coincided with playing Boston six times in less than two weeks. New York was 1-5 against the Red Sox over that stretch This was also when the team’s flaws all collided at once. The offense fell asleep, bullpen imploded, and the pitching staff (namely Max Fried) hit a wall where simply nothing was working. Playing from behind was practically the norm for two months.

Luckily for the Yankees, they managed to take two out of three against Boston earlier this month. The only downside, Boston lefty and Cy Young contender Garrett Crochet pitches Game 1 on Tuesday. He was 3-0 with a 3.29 ERA in four starts versus New York in 2025.

That alone makes this Yankees-Red Sox Wild Card a redemption series. At least on New York’s end.

It’s been twenty-one years since the 2004 awfulness. It still stings, and Boston having the Yankees’ number since in every postseason series doesn’t help.

Moreover, it’s an interesting callback to 2018, albeit in a Bizarro way. The Yankees were first in the AL East and won the Pennant ant 94-68 last season, their same record as ’25. Only difference, finishing tied with the Blue Jays and losing the tiebreaker bumped New York down to Wild Card. They may not have won 100 games like in ’18, but the talent damn near matches.

One way or another, this isn’t the Yankees or Red Sox’s series to win. It’s either of theirs to lose. Now, let’s see which side shows up more.