Would the Red Sox be the Yankees’ toughest challenge in the Wild Card Series?

No matter what happens over the next five days, the New York Yankees will play in October. That much is known, following Jose Caballero’s walk-off RBI single to defeat the White Sox on Tuesday. Everything else, however, is up in the air.

The Yankees are tied with the Blue Jays in the AL East, their closest encounter since early July, but still need to make up a game in four days because of losing the tiebreaker. They sit three games ahead of the Red Sox for home-field advantage in the Wild Card Series, and a combination of two more Yankees wins and/or Red Sox losses will clinch, at least, the No. 4 seed. Boston’s only avenue to leapfrog or beat them through their own tiebreaker is to go undefeated while the Yankees go 1-3 or 0-4, or to go 3-1 while the Yankees go winless against the White Sox and Orioles in the final four.

If the Yankees remain in the No. 4 seed, they could potentially face four different opponents. The Mariners clinched the AL West last night, so they’re out of the picture for the Wild Card Series since they’re a win or a Guardians loss away from securing a first-round bye, and even in the doomsday scenario where Cleveland surpasses them, the Yankees can’t fall to the No. 6 seed at this point for that matchup.

This leaves Houston, Detroit, Cleveland, and Boston all in play. On Tuesday, Nick dove into the Astros as part of his article weighing AL West matchups, while Josh looked at the surging Guardians and slumping Tigers in the AL Central.

But everyone knows that the most intriguing matchup in terms of narratives would be a clash with the Boston Red Sox. The Yankees have lost three consecutive playoff matchups to their rivals, and this is really only the second time in seven years that both teams appear ticketed for October. It might not be the early-2000s anymore, but The Rivalry is still on fire.

There’s a degree of nervousness when playing a rival in October. As a fan, you not only root for your own team’s success, but also for your rival’s failure. While beating a rival in the playoffs can bring tremendous joy, losing to a rival can bring unbearable despair. Adding to the potential nervousness? Boston went 9-4 against the Yankees this season, including 5-2 at Yankee Stadium. As an added point, they also easily won the most recent Reacts poll about the Yankees’ toughest possible Wild Card Series opponent.

But, removing the mental aspect (indeed, Aaron Judge and Giancarlo Stanton are the only Yankees on the active roster who played in the 2021 Wild Card Game), are the Red Sox the biggest foes for the Yankees in a potential Wild Card Series? Let’s weigh why or why not.

Rotation

Two words. Garrett Crochet.

The likely runner-up in AL Cy Young voting, Crochet has seen the Yankees four times this year and has not taken a loss. While his first and most recent starts weren’t as dominant as the middle two, he still managed a 3.29 ERA with 39 strikeouts in 27.1 innings. He provides length, and the only damage they’ve managed off him all season is the occasional home run.

Brayan Bello is their likely Game 2 starter, and he’s fared very well in his career against the Yankees, while being in the midst of the best season of his young career. The Yankees jumped all over him during his most recent start, which would be the game plan for him. While opponents slash .266/.343/.435 the first time through against Bello, the OPS drops to around .600 after that, including a .224/.307/.313 slash the third time.

As for Game 3, it’s probably Lucas Giolito, who’s having a fine season but has screamed potential regression. His command has been erratic lately, walking 29 in his last nine starts over 49 innings. His peripherals haven’t looked strong, and of the three, the Yankees have done the best off of him, albeit in two starts. While he is clearly their No. 3, he’s also lined up to start Game 162, which might still be needed, depending on how these games go for Boston. If he does pitch on Sunday, it would open the door for Game 3 to be some combination of young starters Kyle Harrison, Payton Tolle, and Connelly Early.

It’s fair to say that in a short series, you can be worried about Boston’s rotation. Crochet will likely force multiple lefty mashers to the bench and for New York to rely on guys like Austin Slater and Amed Rosario. Bello has induced soft contact all season from the Yanks, and Giolito is a steadier third starter than whoever the Yankees match against him.

Lineup

The big question mark for Boston’s lineup is Roman Anthony’s health. The former top prospect and likely AL Rookie of the Year finalist suffered a Grade 2 oblique strain at the start of September, and his October availability is unknown. As of Tuesday, Anthony had still not resumed baseball activities, just a week before the playoffs begin. Desperation breeds some crazy things, so you can’t rule out an unlikely return, but it looks bleak for at least the Wild Card Series.

Several BoSox hitters are in deep slumps. In the second half, Alex Bregman has not been himself, although that means nothing considering he almost had as many hits against the Yankees as he did against everyone else for about a month. Ceddanne Rafaela, an elite defensive center fielder, hasn’t been able to hit water if he fell out of a boat in the same span. Trevor Story has been the most consistent hitter in their lineup. Imagine that.

Their lineup against lefties (IE, their likely lineup in Games 1 and 2) consists of lefty mashers Rob Refsnyder and Romy Gonzalez but also features Nate Eaton, Nick Sogard, and even Connor Wong. The Red Sox thrive with their platoonability (is that a word?), so as soon as the Yankees deploy their bullpen in those games, expect an army of lefties, including Nathaniel Lowe and Masataka Yoshida, although both are also in slumps.

Bullpen

Here’s where things get really tricky. Although the Yankees are among the best teams in baseball at hitting left-handed pitching, it’s safe to say you probably don’t want to face lefties the entire game, right? Fortunately, most teams aren’t able to stack lefties like that unless a lefty starter goes the distance. The problem is that Boston is a team that can.

Crochet going six innings, regardless of runs allowed, feels like a sure thing. After that, the Red Sox will likely go to Justin Wilson, Garrett Whitlock, and Aroldis Chapman if they have the lead. Wilson and Chapman are lefties, so you’d only have one inning to deploy your lefty bats.

The real problem is if Crochet goes seven. Although Whitlock is their traditional setup man, Alex Cora could absolutely deploy Wilson and Chapman and not give Aaron Boone a chance to counter with a Ben Rice, Trent Grisham, or Jazz Chisholm Jr., depending on how the lineup shakes out.

Of course, Boston’s bullpen is good enough even without thinking of potential matchups. Steven Matz has been effective as a medium leverage lefty, former Yankee Greg Weissert has gotten big outs for them all season, and the previously mentioned Tolle can flash triple digits on an overpowering fastball if he’s moved into a one-inning role in the playoffs.

Miscellaneous

The Red Sox lead MLB in errors, but they aren’t a bad defensive team. Their only negative defenders are Story and Gonzalez up the middle, while they have elite defenders behind the plate, in center field, and right field. Their issue, like the Yankees, is the boneheaded mistake that overshadows the good. They lead the majors in catcher’s interference, and they seem to make their mistakes in the biggest moments. Last week against the A’s, Story cost them runs in two separate innings with a pair of errors in a two-run loss.

The Red Sox are also the sixth-best baserunning team in the majors, according to BsR. They are among the most aggressive baserunners in the majors, taking extra bases at an elite clip. The downside to aggressiveness, however, is getting caught. They can bail out the other team with ill-advised aggression, as they did last time they played the Yankees when they were threatening off of Max Fried.

So, are they the biggest threats?

It’s still hard to say. There are a lot of things in baseball you can’t measure with stats, so although the Boston offense has a 90 wRC+ since Anthony went down, you never know what can happen. While Crochet and Bello have done well against the Yankees, both are making their postseason starting debuts. Truthfully, we won’t know until we get to October. Here’s hoping that the AL East breaks New York’s way and renders this whole discussion moot for at least the first round.