MLB Playoffs: Red Sox vs Yankees AL Wild Card Pick — MLB’s Biggest Rivals Meet in the Playoffs Again

• In the Red Sox-Yankees MLB Wild Card battle, these two historic rivals renew acquaintances
• Boston (89-73) endured a difficult first half of the season after playing poorly and stunningly trading star Rafael Devers, and made the playoffs as a Wild Card
• New York (94-68) missed out on the AL East title because of losing the head-to-head series against the division champion Blue Jays
• The Red Sox won 9 of the 14 matchups between the teams in 2025

The Red Sox Are Built for the Postseason

The BoSox have two things the Yankees do not have: A hot starting pitcher at the top of the rotation and a dominating closer.

Garrett Crochet is an AL Cy Young Award contender. In his first season in Boston, he won 18 and lost 5, had a 2.59 ERA, and led the majors in K’s (255) and innings pitched (205.1).

Crochet started 4 games against New York in the regular season, accruing a record of 3-0 with a. 3.29 ERA. He struck out 39 in 27.1 innings, allowed 20 hits, 10 runs, and 5 homers. He had a 13-2 record on the road with a 2.25 ERA.

Former Yankees closer Aroldis Chapman enjoyed a career renaissance in Boston. He was an All-Star and posted a 1.17 ERA in 67 games, striking out 85. He saved 32 games and will get a few CYA votes of his own.

Boston is not the slugging team they have normally been in recent years. Trevor Story led the club with 25 homers, but they had seven hitters in double-digits. They also have base-stealing prowess. Story stole 31 bases and was caught once. Jarren Duran stole 24. Ceddanne Rafaela stole 19 in 24 attempts and is perhaps the best defensive center fielder in the game. Rookie Roman Anthony accrued a 3.2 bWAR in 71 games with 8 homers and an .859 OPS.

The Yankees Begin and End With Aaron Judge

Aaron Judge is the sun around which the Yankees’ universe rotates. He posted a 9.8 bWAR, hit 53 homers, and led the majors in batting (.331), on-base percentage (.458), slugging (.691), and OPS (1.149). He led the AL in runs scored. Winning his third MVP is in question after the year the Mariners’ Cal Raleigh had, but Judge probably deserves it.

The rest of the Yankees’ batting order is productive. Jazz Chisholm was a 30-30 player. Trent Grisham hit a stunning 34 homers. Cody Bellinger hit 29; Giancarlo Stanton hit 24; Austin Wells added 21; and Ben Rice 24.

Ace Max Fried won 19 games and logged 195.1 innings. However, his ERA was more than a run higher in the second half of the season than it was in the first. He pitched well against the Red Sox with a 1.96 ERA in 3 starts.

Behind Fried, they have Carlos Rodon. He was 18-9 and tied for the MLB lead in starts with 33. In 195.1 innings, he struck out 203. Rookie Cam Schlitter was impressive in 14 starts with 84 K’s in 73 innings and a 2.0 bWAR.

The bullpen stabilized when they acquired David Bednar from the Pirates. He has taken over as closer from Devin Williams and Luke Weaver. While Williams seemed to have righted himself late in the season, he does not seem to have the stomach for New York or the big game. If they trust him in a big spot, they will regret it.

Red Sox vs Yankees MLB Wild Card Pick

In our Red Sox-Yankees Wild Card pick, this is arguably the bitterest and longest-standing rivalry in sports. They truly despise each other from top to bottom, and when they are in the most competitive situations of the playoffs, the intensity is exponential.

Since it’s such a short series, the key is Crochet. If New York wins the game he starts, they are likely to win the series. Unlike past series between the teams, they do not bash each other into oblivion with home runs. The Yankees need home runs to win, but the Red Sox have different ways to beat them.

Expect a pitched battle that will go down to the third game, with the Red Sox ultimately coming out on top.