The Yankees and Red Sox will face off again on Tuesday night, but this time the stakes are higher than just bragging rights for the regular season. The Yankees and Red Sox play each other for the first time in October since 2021 in a best-of-three Wild Card Series at Yankee Stadium. This will be the sixth time these two bitter rivals have met in the playoffs. The Yankees will be out for revenge after losing the season series 9-4 to Boston.

Aaron Judge had a season for the ages, hitting 52 home runs and winning his first batting title with a .331 average. He had the highest bWAR (9.7) in baseball and an amazing OPS of 1.144. Aaron was the third player to win a batting title while hitting 50 or more home runs, joining Babe Ruth and Sammy Sosa. He had no trouble going back to right field, with +3 Outs Above Average and only one error in 95 games. But if the Yankees can’t figure out the Red Sox puzzle that has stumped them all season, individual brilliance doesn’t matter.

Clint Frazier, a veteran of the Yankees, gave a strong warning about the risks of the compressed playoff format during his YouTube appearance on Monday. “That’s the one downside of going right into the wild card,” Frazier cautioned. “When you go back-to-back days and some of these guys are just already logged a million innings this season, it does matter.” He stressed that October’s relentless pace leaves no room for error. “Fatigue is going to be a serious factor,” he warned, explaining how the Yankees need to use creative strategies in their bullpen to stay alive.

Frazier talked about situations in which starters like Carlos Rodón could pitch four or five innings before giving the ball to long relievers like Luis Gil or Will Warren. “You probably will see some games where one of these starters might piggyback off the other starter,” he said, describing how this approach could preserve arms while getting “straight to the ninth inning with Clay Holmes, game over.” 

Max Fried’s recent problems with fatigue make the Yankees’ pitching problems even worse. The ace has given up at least four runs in each of his last six starts, and his ERA during that time is 7.20. He has had problems with blisters that keep coming back since his time in Atlanta, which makes it hard to know how effective he will be when the Yankees need him most. Fried gave up five runs in just two innings on Saturday against St. Louis, but he settled down and finished the game with five frames.

Manager Aaron Boone knew that Boston had been the best team all year, but he was hopeful after New York won the last series. “They got the better of us this year,” Boone told the New York Post. “We won the last series. It’s always a battle. It’s coming down to three games between the two of us. Hopefully, we can back up our last series with another series win against them.” The home crowd at Yankee Stadium might provide the edge that New York desperately needs.

But just having faith won’t fix the Yankees’ biggest problem. They have to beat a pitcher who has made them look bad all season before they can even think about going deep in the playoffs. That challenge comes right away on Tuesday night.

Crochet casts a shadow over the Yankees’ wild-card hopes

Boone’s hope will be put to the test right away against a pitcher who has been a pain in the neck for his team all season. The left-handed pitcher has beaten New York every time they’ve met this year, making their strong offense look like a group of confused hitters watching strikes go by.

Crochet comes into his first postseason start with a lot of momentum that few pitchers can match. The Red Sox gave up four prospects to get him out of Chicago, and that investment paid off big time. In 2025, Crochet had a record of 18 wins and 5 losses and an ERA of 2.59. He also led all of baseball with 255 strikeouts. “He’s turned in for them,” Boone admitted Monday. “Crochet’s clearly become their ace and their horse. And from what I understand, been phenomenal behind the scenes, too.”

The numbers show that Yankees hitters are in a lot of trouble. This season, they only had a .601 OPS against Crochet, with only 20 hits in 100 at-bats. His dominance goes beyond just numbers; he struck out 39 batters in four starts against New York, including Aaron Judge, who struck out 11 times.

Crochet completely owns the Yankees. He has a perfect 3-0 record against them, with a career ERA of 2.90 and 45 strikeouts. All three of his wins came after he joined Boston. The Yankees need answers that they haven’t been able to find all season, and they need them right away.