What scares you about the Yankees?
The possibility that they find out that Jose Caballero is a much better shortstop than Anthony Volpe.
— Jacob Roy
The fact that the Yankees have seen Garrett Crochet four times already this season. In those matchups, Crochet has had two meh starts (mostly due to the horrendous Boston defense in the first half of the season), and two Crochet-esque starts, but just the fact that they’ve seen his stuff so much already is a bit troubling for me.
But to be fair, his xFIP against the Yankees this year is nearly
a run and a half lower than his actual FIP, so perhaps my concerns will pass.
— Avery Hamel
The short porch.
— Juliet Hurwitz
That Aaron Judge thinks it’s still the regular season.
— Bob Osgood
Their ballpark’s short porch in right field. They have a lineup designed to take advantage of it and the Red Sox do not.
— Matt Gross
The one guy who is very large and sometimes good. Sometimes he breaks his toes.
— Mike Carlucci
If Judge finally gets going in the postseason.
— Maura McGurk
The chance that the Yankees rotation clears enough to make life hell on the Red Sox lineup.
— Jake Reiser
Ben Rice. While it might be strange to be fearful of a catcher, he’s already got four home runs against the Red Sox in his career, even if three came in the same game, to go with 11 RBIs. Plus, his “Yankees fan who grew up in Massachusetts” archetype is already so tired. He might be managing this Yankees team in two decades or so with one clutch hit in this series.
— Dean Roussel
What scares you about the Red Sox?
The middle relief. I know Alex Cora gets crazy in the postseason, but I’m worried about what happens if Zack Kelly or Greg Weissert find themselves in a big spot.
— Jacob Roy
The constant men they’ve been leaving on base. There are no more makeup games. Every scoring chance has to be capitalized on to move forward, and seeing multiple bases-loaded opportunities squandered in the past weeks is not a an awesome sign.
— Jake Reiser
Jake says high LOB numbers, but I raise you: No offense at all. There have been too many games since Anthony’s injury where the offense hasn’t performed well or gotten more than 2-3 runs. Against the Yankees, we’re very likely going to need more than 2-3 runs per game.
— Juliet Hurwitz
The lack of thump in the lineup. The one thing the Yankees did better than any team in baseball was score runs and hit home runs. If they put a crooked number on the board early, I fear that this Sox lineup, specifically without Roman Anthony, is a bat or two short to catch up.
— Bob Osgood
Continuing the theme from the first question and on Bob’s point above, the Red Sox do not have an obvious candidate to put the the fear of God into Yankee pitching from the left-handed batter’s box. For years, they had David Ortiz in this role. Then, the torch was passed to Rafael Devers, and now, it seems like it’s been passed Roman Anthony given that he hit one of the most declarative regular season home runs I’ve even seen in his first ever trip to Yankee Stadium back in August.
But now, the Red Sox will not have that guy in this series, and it puts them at a significant disadvantage in the series given the ballpark’s dimensions.
— Matt Gross
Starting pitching after Garrett Crochet.
— Mike Carlucci
Our offense can be so anemic sometimes! Whether it never gets going, or waits until late in the game and then runs out of time…this will keep me up at night.
— Maura McGurk
Is it bad to say it’s Aroldis Chapman pitching in the postseason at Yankee Stadium? I’m going to say it’s Aroldis Chapman pitching in the postseason at Yankee Stadium.
— Avery Hamel
Whoever is starting game three, should it come to that. I’m not worried about Bello since his ERA is under 2 against the Yankees (small sample size, but justified.) But Early/Harrison/insert starter here against the up-and-coming Cam Schlittler (a Massachusetts native who did NOT grow up a Yankees fan) will be a nail-biter no matter who it is.
— Dean Roussel
What’s one thing you really want to see happen?
Another Devin Williams postseason implosion would be great. I don’t think it will happen, but it would be funny to see. Especially because he’ll be signing with the Red Sox this winter (bookmark this).
— Jacob Roy
The Red Sox taking the early lead. Seeing Garrett Crochet eat in Toronto last week with a three run lead was delicious. It’s even more imperative for Bello and whoever gets the bump in a potential Game 3 to have some buffer.
— Jake Reiser
The return of Playoff Judge. The Yankees like to follow his lead, so if he falters, they very well could too.
— Juliet Hurwitz
Silly baserunning, shaky defense, and poor managing failing the Yankees again. We saw it in the playoffs last year, we saw it in numerous games against the Red Sox during the regular season (with the Sox going 9-4 head-to-head), and it will lead to their demise at some point in these ‘25 playoffs.
— Bob Osgood
For the Red Sox to not just win, but win big and win quick. The team’s fortunes this October will ride heavily on their ability to use the staff’s top end pitching in the rotation (Crochet and Bello) and in the bullpen (Whitlock and Chapman) to smother opponents early. The playoff format is designed so that the early part of October is littered with off days for teams who advance quickly, and if the Red Sox can then take advantage of this with their strong top-end pitching right out of the shoot, they then would be able to rest their arms, turn everything around, and do it again without ever showing the weaker part of their staff to an opponent until deep in the ALCS. This is the formula to make a deep run!
— Matt Gross
A Jarren Duran steal of home.
— Mike Carlucci
I’d love to see all (or most) of our offense click at the same time. We’ve gotten used to seeing several players slumping at once but I want to see us run the board like I know we can.
— Maura McGurk
I need to see a Brayan Bello dominant playoff start against the Yankees on the road more than I need air to breathe. I need Pedro Martinez to call him before he takes the bump, pump him up, remind him that he’s actually the Yankees’ daddy, and inspire pure greatness from him. Also, I need all of the above to be recorded and played after Boston maybe wins the series (that’s the most optimism you’ll get from me).
— Avery Hamel
What Avery said. Bello dealing in Game 2 would be amazing and an exclamation point on a huge season of growth for him.
— Dean Roussel
Who will be the MVP of the series?
Garrett Crochet. He’s probably the guy who can come closest to winning a game on his own.
— Jacob Roy
Aroldis Chapman. All season, the Cuban Missile has been nothing short of dominant. In a close game late, I’d trust him with my life this season against Judge, Stanton and Bellinger.
— Jake Reiser
Masataka Yoshida. I’m putting $8 billion on it. I’m only half-joking, but I’ll let you figure out which half is the joke.
— Juliet Hurwitz
Alex Bregman. He’s played 99 playoff games, 17 of those are against the Yankees. He won’t be intimidated by the moment.
— Bob Osgood
I’m hoping it’s Garrett Crochet because if it’s not, there’s a good chance it’s a Yankee.
— Matt Gross
Rob Refsnyder. The first two games are against lefties. It’s his time to shine.
— Mike Carlucci
Garrett Crochet.
— Maura McGurk
I’m serious when I say that the performances of Rob Refsnyder and Masataka Yoshida combined could decide this series for Boston. That being said, I have faith in future #MyManager Rob Ref and Yoshida looked like the only people remotely interested in going to the postseason before Ceddanne Rafaela’s walk-off last Friday.
— Avery Hamel
I’m feeling Trevor Story having a huge series. I would have called myself absolutely nuts had I said this five months ago.
— Dean Roussel
Which non-star will have a Dave Roberts/Brock Holt/Steve Pearce, moment and what will that moment be?
Connor Wong will hit his first home run of the season, assuming he continues to catch Brayan Bello in game two.
— Jacob Roy
Nate Eaton—between his speed and penchant for contact hitting, he’s going to do something that rattles the Yankees just enough to keep things interesting and become a cult hero.
— Jake Reiser
I’d honestly say Ceddanne Rafaela, even though he’s had his share of Star Moments/Huge Impact Moments this season. Given how he’d been faring offensively in the second half, I think he’s warming up again, and I think he’s gonna love the playoff atmosphere so much that he makes a big splash, whether that’s getting a big homer in the top of the ninth or a go-ahead hit at some other point.
— Juliet Hurwitz
Rob Refsnyder. He’s got Fried in Game One and Rodon in Game Two, and he’s got a .302/.399/.560 slash line vs LHP with a 159 wRC+ in 2025. .281/.383/.443 with a 129 wRC+ vs LHP in his career. Refsnyder will presumably be out there and hitting in an important lineup slot.
— Bob Osgood
I’ll go with Masataka Yoshida simply for his ability to take a big situational at-bat and have success. (See the last World Baseball Classic.) My hope is he hits an important home run over the short porch in right field and becomes “that guy” for a day.
— Matt Gross
Romy Gonzalez. A bases-clearing double in Game 2 off a lefty that gives the Sox a lead they don’t surrender.
— Mike Carlucci
Ceddanne Rafaela. He’s shown a penchant for big moments at the plate, especially in the later innings. Combine that with his defense and his speed, and I think he might put on a real show. I’m counting him as a “non-star” because he’s still flying surprisingly (to me) under the radar outside of Red Sox Nation—but I think that starts to change with this postseason.
— Maura McGurk
Call me crazy, but Nathaniel Lowe has been here before with the Rangers in their World Series-winning season. And I foresee a very strategic plate appearance that ends in a walk or a bases-clearing double being a key moment in the series. Maybe he’ll corral some of Trevor Story’s throws at first too, idk.
— Avery Hamel
I’m agreeing with Carlucci on the Romy prediction here. As said earlier, I also think it’s very plausible Ben Rice will have a Boone moment.
— Dean Roussel
What dumb thing will Yankee fans do?
Besides roll call?
— Jacob Roy
Loudly boo the Red Sox and get put in their place at least once in this series. Even if they have the last laugh, they’re going to get brash and bitten for it.
— Jake Reiser
Say, “We want Boston” if they win Game 1, only to remember they should never want Boston in Games 2 and 3.
— Juliet Hurwitz
Throw a drink on a key player’s wife like they did at Bethpage Black over the weekend? Just, the worst.
— Bob Osgood
Get into it with Jarren Duran in the worst ways possible.
— Matt Gross
Throw enough trash on the field that there is a delay of game.
— Mike Carlucci
Whatever it is, we’ll look at each other and collectively say, “You can’t make this shit up.”
— Maura McGurk
They somehow look goofy just showing up to a game. So, I think that should do it.
— Avery Hamel
Let us win tonight.
— Dean Roussel
What’s your prediction for the series?
2-1, Red Sox.
— Jacob Roy
2-0 Sox. Huh, you don’t even give the Yankees a chance? It’s not that the Yankees won’t make this a competitive series; they will at every turn. What this series is going to come down to is competency in two major ways. The Yankees play boneheaded baseball. They get saved more often than not but when they make mistakes, they’re costly. Every in-game decision is going to require the utmost competence as well. I wouldn’t trust Aaron Boone as far as I could throw him to make the right choices in a difficult spot. I do trust Alex Cora. Those are the X-factors and if the Red Sox take Game 1, I see it unraveling in Game 2.
— Jake Reiser
Man, I dunno. I wanna be optimistic but I’m also scared. It’s my first time being this invested in a Sox postseason since 2013!! I’ll say 2-1 Sox, and we take Game 1, somehow drop Game 2 because the offense doesn’t give Bello run support, and miraculously take Game 3 even without Giolito.
— Juliet Hurwitz
For some reason, 10 of the 12 series have been 2-0 sweeps since MLB switched to the three-game format. And since the Red Sox are going to win: 2-0 Red Sox.
— Bob Osgood
I think it goes 2-0 either way and all depends on Garrett Crochet. If he shuts down the Yankees for a win the Red Sox take the Wild Card. If he doesn’t, Yankees roll over the sleepy Sox.
— Mike Carlucci
2-1 Sox. If it’s 2-0, I certainly won’t complain.
— Maura McGurk
I’m with Mike on this one. I can genuinely see it going either way. BUT as a regretfully negative fan in general, I think it’s good news that I see a way out for the Sox in this series. With that being said, I think Boston squeezes one out 2-1. Losing Lucas Giolito genuinely isn’t that big of a blow to Boston (sorry), though the thought of having a rookie or Kyle Harrison on the mound for game three certainly isn’t comforting. And if the offense can show up like it did in the August series against the Yankees and not the September one, they can get away with some inconsistencies.
— Avery Hamel
I’m contrarian as always so I’ll go 2-1 Yankees after a dominant Game 1 Crochet appearance, but if the Yankees do advance, I can’t see any way the Yankees break this 15-year streak of no World Series THIS season. But I sure hope I’m wrong. The Red Sox feel special this year, so if they make it past the Yankees, who knows what happens?
— Dean Roussel
My head says a matchup on the road against tough lefties is exactly the type of matchup that spells trouble for the Red Sox. But then my heart says that the Yankees suck. And then my head is like “oh yeah, the Yankees do suck, how could I forget about that?“ 2-0 Sox.
— Dan Secatore
