Yankees vs. Red Sox MLB Wild Card series preview and prediction for 2026 Playoffs

Yes, it’s looking like Aaron Judge will not be available for the Yankees in the Wild Card round and potentially beyond, and no matter how you slice it, that’s a disaster for New York. Judge is the best hitter in the world, and their offense without him isn’t all that scary, particularly against left-handed pitching.

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This will have major domino effects on the series, and I would wager that the Red Sox’s apparent decision to load up rookie left-hander Payton Tolle for Game 1 has a lot to do with Judge’s absence. Tolle is easily their highest upside pitcher, but he’s never been in anything close to that kind of spot in his life. He’s as competitive as they come, but a hostile Bronx crowd will be a serious pressure cooker.

Ok, now onto the mega preview. While it is theoretically possible that the Red Sox do not play the Yankees in a three-game all-the-marbles showdown in the Bronx in one of the American League Wild Card series, it would take an impossibly specific AL Central finish for Boston to somehow tank their way to an easier matchup. I feel confident publishing this now, and if I wind up being wrong … well, I’m just going to assume that’s what God wanted. The Yankees and Red Sox are currently fourth and fifth overall in FanDuel’s World Series winner odds, so it should be a pretty even matchup.

I wrote a lengthy breakdown of the pitching matchups in this series earlier this month, and speculated that Boston would go with Sonny Gray in Game 1 with Tolle in Game 2, while the Yankees would use Cam Schlittler and Max Fried in some order, though I wasn’t quite sure how healthy Fried was or if Gerrit Cole or Carlos Rodon would get the other nod. That was apparently wrong-ish, as we’ve since received word that Cole will indeed get a start in the Wild Card series, and the way the rest will work out, it’s possible manager Aaron Boone is lining him up for Game 1 with Schlittler in Game 2. That’s a real risk to potentially hang Fried out to dry if the Yankees get swept, but it’s possible he’s just not healthy enough to run out their early and risk needing too much from the bullpen. They will possibly have Rodon in the bullpen, though that wouldn’t be ideal for the rest of their playoff run (if such a thing occurs).

The Red Sox are going with their gut and Tolle, who has looked like a young ace in Garrett Crochet’s extended absence. It’s high risk, high reward, but with how little you can actually control in the MLB Playoffs, Tolle is the one guy with dominant swing-and-miss stuff that could get you a game singlehandedly. Meanwhile, it’s an open question if Crochet will be able to provide a bullpen role in the Wild Card, but as of last week he was throwing 92 miles per hour — still a ways to go. Gray is looking like the Game 2 starter with Ranger Suarez anchoring Game 3. All that seems fine.

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Other than Crochet and reliever Justin Slaten, the Red Sox should be reasonably healthy for the series. They come with one of baseball’s best bullpens anchored by the late-30s Linsanity-run Aroldis Chapman, Garrett Whitlock and new acquisition Erik Miller. They’ll have bulk relief options with Brayan Bello and could even choose to start him in longer series, but I’d be surprised if he had anything to do in the Wild Card series. Only Masataka Yoshida and Curtis Mead and perhaps Eli White would figure into the offense if healthy, and Boston hasn’t relied on any of them for major production all year. Even Tanner Houck is looking like he’ll be back in some capacity, an absolutely shocking development for all who follow his long road back from a UCL tear.

The Yankees, meanwhile, are not so healthy. Their bullpen is stacked, as is their starting rotation, and I grant them a notable pitching edge over the Red Sox. But their lineup is just decimated. Trent Grisham may not be on the Wild Card roster, and with both Aaron Judge and Giancarlo Stanton out as well, the Yankees are going to be relying on players they’d rather avoid; Max Schuemann, Amed Rosario and perhaps even Anthony Volpe could mix in. That’s not anyone’s idea of Murderers’ Row.

So what’s at stake for everyone? For New York, it all hinges on Judge. If he’s not available at any point, it is borderline unserious to project the Yankees to win four rounds. But they really do have stacked pitching, and you can get pretty damn far on just pitching in the MLB Playoffs if you can get a few lucky hits. For the Red Sox, making it out of the Wild Card for the first time in 2021 is essential. They just canned the interim tag on now-official manager Chad Tracy and signed him to a three-year deal; the organization is committed to this team, this philosophy, and this season.

There’s also the emotional preview, which I will run through quickly: Red Sox/Yankees isn’t necessarily the same rivalry as it used to be, but it’s starting to work it’s way back into the cultural zeitgeist. This is two straight years of Wild Card action, and Boston’s last three playoff series came against

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Here’s the deal: if all were fair and healthy, I would pick the Yankees. The three-man rotation of Cole, Schlittler and Fried is just out of this world, though I don’t necessarily agree that Cole deserves the start more than Rodon. But this is a cruel world, and Boston’s lineup is significantly better than New York’s. Roman Anthony, Ceddanne Rafaela, Adley Rutschman, Willson Contreras and Wilyer Abreu are a rock-solid one through five, and there’s no more black holes in the lineup with a major bench/pinch-hitting advantage. There’s still a chance they just get mowed down by Schlittler and Fried, but Boston’s rotation isn’t that much worse. But it’s a fascinating series, but I’m picking the Red Sox to win in three games. We’ll give Schlittler game two, and then Boston advances to play Tampa Bay. One day, I’ll pick the Yankees in this column. But it is not this day!