The New York Yankees ended their season with an eight-game winning streak with an impressive AL-leading 94-68 record. Unfortunately, the Toronto Blue Jays had the exact same record, and as the Blue Jays won the head-to-head season series 8-5, they were crowned AL East champions. And they will directly reach the division series because of this tiebreaker, and the AL top seed and the Yankees will face the Boston Red Sox, who dominated the season, winning nine of their thirteen games.

The Red Sox even outscored the New York 54-31 in their first nine meetings. And the biggest challenge ahead of the Yankees will be facing Boston’s ace Garrett Crochet, who has never lost a game in his career against them in his seven appearances with a 2.90 ERA and 45 strikeouts. So,  when Aaron Judge was asked about facing him after the final game of the season, Judge was honest to say:  “He can run it up to 100 miles an hour… He’s a tough matchup. You know, it’s probably why he’s, you know, if not one of the best, the best pitcher in the game right now and probably on his way to a Cy Young.”

Is it true? On paper, the 2025 season belonged to a few elite arms like Detroit Tigers ace Tarik Skubal and Pittsburgh Pirates ace Paul Skenes. And Skubal was the heavy favorite for the AL Cy Young award with his 13-6 record, AL-best 2.21 ERA, and a league-leading 0.89 WHIP. Skenes, on the other hand, dominated the National League with a historic 1.97 ERA and modest 10-10 record despite the team’s poor performance. And Crochet? With an 18-5 record and a 2.59 ERA, Crochet’s performance so far has been one of the best, if not the best. Plus, he also led the American League in both strikeouts (255) and innings pitched (205.1). So, every word the Judge said was completely true.

Now, look at the personal duel between Judge and Crochet this season. In June, Crochet struck out the Yankees’ captain six consecutive times. But Judge got his revenge on June 13, after ending the streak by hitting a game-tying home run at Fenway Park. And on their final meeting on September 14, Crochet struck out Judge twice. But Judge launched a 98-mph fastball for a home run once again.

But in short, the Boston ace has completely owned the matchup, striking out Judge 11 times in 15 at-bats overall. It’s a 73.3% strikeout rate against the likely MVP.  But when Judge does make contact, the ball leaves the diamond. Two of his three career hits off Crochet are home runs with a .600 slugging percentage.

And, while Judge’s battle with Crochet will be the headline, the Yankees must be ready to face the entire Red Sox roster to advance.

Beyond the Boogeyman..

The Red Sox offense is balanced and dangerous, led by shortstop Trevor Story with 25 home runs and 96 RBIs. The lineup also features threats like Alex Bregman and Wilyer Abreu. They finished fourth in the majors in batting average (.254) and sixth in stolen bases. This means they don’t just rely on home runs, and they don’t even need to. And Masataka Yoshida, who struggled after his July return, went 13-for-34 with two doubles and a triple in his last eight games. Ceddanne Rafaela is also hitting .424 with five doubles and a triple in his last 33 at-bats.

Boston’s pitching is also more than just Garrett Crochet. Brayan Bello, who has an ERA of  1.89 this season, will start Game 2. Their bullpen, anchored by the powerful duo of Garrett Whitlock and former Yankee Aroldis Chapman, is another major strength. The team has finished with the fifth-best team ERA in all of baseball (3.70) with this depth. But there is some good news for the Yankees.

Star rookie outfielder Roman Anthony isn’t coming back soon. Key hitters like third baseman Alex Bregman and first baseman Nathaniel Lowe have also been struggling lately at the plate. And though Jazz Chisholm Jr was out of the Game 162’s lineup, he will be in the lineup. So, if the Yankees’ pitchers can take advantage of these slumps and injuries, they might find an edge.

And of course, the Yankees have their own demons to face. Aaron Judge has a well-documented postseason struggle. And his career playoff batting average is .205. Plus, their offense is often “all-or-nothing,” relying too much on home runs. So the question remains: Can Aaron Judge lead the Yankees past their rivals? Or will the Red Sox boogeyman end their season? Share your predictions in the comments below.