OTM Roundtable: What are you scared of, what do you want to see, and who will win?

The rotation. Cam Schlittler, Max Fried, and Gerrit Cole are one of the few groups that have been as good as the Red Sox’s top three. That, combined with a Red Sox offense that has been lethargic in September, could make for a difficult series.

— Jacob Roy

The pitching. One of the few teams with as good or better pitchers than the Red Sox: the Yankees. The Sox are already struggling to hit consistently; the last thing I want is to see New York roll out three aces. (Well, maybe 2.5 with the 2026 version of Garrett Cole.)

— Mike Carlucci

The pitching. And yes, there’s an echo in here, but it’s also the right answer. If you could play this series in a simulation a thousand times, I’d be willing to bet that over 90 percent of the Red Sox losses come from the lineup just not bunching enough hits, not hitting for enough power, and not being about to knock in enough men with runners in scoring position against the Yankee staff.

— Matthew Gross

Hate to repeat what everybody else is saying here, but yeah: New York has one hell of a pitching staff. When you’ve got the soon-to-be AL Cy Young winner staring you right in the face in the first game of a short series, it’s a tall task. Luckily, I think the Sox have a comparable pitching staff—at least among the trio of starters that are lined up for the Wild Card—but the Yankees’ starters are formidable.

— Fitzy Mo Peña

Cam Schlittler and Ben Rice. Did you know they’re both from Massachusetts?? Is anyone going to write a story about this!?

— Bob Osgood

The answer is the pitching, but you know that already. So let’s get a little creative and say something else: home runs. The Red Sox pitching staff allowed the fewest homers in baseball this year. But the Yankees lineup hit the most homers in baseball this year. I’m expecting the Sox to struggle to score, so even if the Sox get a great outing from the starter, one back-breaking dong in the 7th could decide the game.

— Dan Secatore

The bullpen. Without Tyron Guerrero, the only arms I truly trust are Garrett Whitlock and Aroldis Chapman. Erik Miller and Brayan Bello are meltdowns waiting to happen, Garrett Crochet is a total mystery, and the rest of the guys just aren’t that good. If the starters can’t go deep, it’s going to be difficult to hold leads.

— Jacob Roy

Jarren Duran. I’ve been… critical… of the much-maligned outfielder throughout the majority of his career, but something tells me that, given the ways things have unfolded over the last few weeks (Mickey Gasper’s injury, Andruw Monasterio being bad) he’ll be forced into the lineup against right-handers and open up the opportunity for the spotlight to be placed directly on him. I hate that.

— Keagan Stiefel

The pitching. If Tolle/Gray/Suarez go 5.0-6.0 innings with 2-3 runs are the Sox scoring that many? Are the big arms entering the game down by 1? Down by 2? 

— Mike Carlucci

Their complete inability to hit high velocity pitching, which the Yankees have in spades. Mickey Gasper was actually even one of the better guys at doing this, and now he’s on the shelf too. Somebody’s going to have to step up and have a huge series at the plate because on paper they lack the firepower to counteract the Yankee arms.

— Matthew Gross

The issues with runners in scoring position are unbecoming. This team ended with a .709 OPS with RISP in 2026, good for 26th best in MLB (wow, that’s a lot of initials; it’s like alphabet soup). This is especially worrisome considering my aforementioned point about the pitching that the Sox will be going up against; if/when you do get some traffic on base, you have GOT to take advantage of it. These trends can’t continue….but I’m nervous that they might.

— Fitzy Mo Peña

The offense, specifically the lack of power and struggles with runners in scoring position. Boston was 25th with RISP this season, with a .241 batting average, and it was far worse in September. They also finished 26th in baseball with 163 home runs, an issue that Craig Breslow vowed to fix, but did not fix, after falling short in the playoffs a season ago.

— Bob Osgood

Wilyer Abreu going to the top deck off Cam Schlittler, please and thank you.

— Keagan Stiefel

Jarren Duran steals home.

—Mike Carlucci

Roman Anthony to have a huge series. This would not only be a great first step to counteract New York’s biggest strength, but big picture wise, wouldn’t it be nice if — in Anthony’s first time in a hostile, road playoff environment — he just proved he’s one of those guys that thrives in these high intensity moments? It would be huge not just for this series, but in his growth as a franchise building block.

— Matthew Gross

I’m gonna go out on a limb and say that I’d like to see the Red Sox win the series.

— Fitzy Mo Peña

Payton Tolle to outduel Cam Schlittler in Game One. I love Payton Tolle. And I hate Cam Schlittler.

— Bob Osgood

I’d like to see a pigeon to take a big ol’ dump on Cam Schlitter as he’s bowing his head for the National Anthem before Game 1. We deserve to have nice things.

— Dan Secatore

One time my girlfriend and I were walking, and I happened to look up at the right moment, put my arm out to stop her, and pigeon shit fell exactly where her next step would have been. She never really gave me credit for that heroic act, and I bring it up regularly to this day. Anyway, what Dan said.

— Jacob Roy

Wilyer Abreu. If there was ever a time for the king of streakiness to start turning back in the right direction, it’s with that absurdly short porch staring him directly in the face for three straight games.

— Keagan Stiefel

Nick Sogard. As the man says, you don’t watch him every day and you don’t see what he’s capable of. 

— Mike Carlucci

Probably somebody incredibly annoying like like Jose Caballero. The real MVP will probably be the Yankees pitching staff, but because that’ll be a multiheaded monster without an obvious solo choice, it will be some middle or bottom of the order Yankee bat that manages to get bat on ball and find a hole a couple of times with men on base.

— Matthew Gross

This is the perfect time for Roman Anthony to step into the national spotlight. Lefty at Yankee Stadium with an offense that could use a shot in the arm; why not him? In a short series, it especially only takes one or two big moments to make your mark. This is the Roman Anthony breakout series.

— Fitzy Mo Peña

Wilyer Abreu. I’m glad he was one of the players from the Sox core who got his first playoff reps in the Bronx a year ago. He’s due, and when he gets hot, look out.

— Bob Osgood

With Willson Contreras ailing, I was convinced that Romy Gonzalez was going to hit a go-ahead home run in the 8th inning of Game 3. That just would’ve been the perfect playoff moment for this team of AAAA overachievers. But with Contreras (thankfully) healthy and back in action, let’s give that moment to Jahmai Jones instead. This is what lefty-killers are for.

— Dan Secatore

Jahmai Jones will get his chances against lefties. He won’t start against Schlittler, but he’ll likely get an at-bat against one of the lefties in the Yankees’ bullpen, plus Max Fried in game two. He’ll hit a multi-run home run in a big spot to give the Red Sox a lead.

— Jacob Roy

Connor Wong. While the “Forever Young” catcher will always be a starter to me, he’s been pushed back for Adley Rutschman. I think he drives in a run with a shallow double just between the shortstop and left fielder. 

— Mike Carlucci

I was gonna say Sogard, but let’s change it up here and go for a wild one. In one of these games, it’ll be the sixth inning or so. Boston will be in a tight spot with a handful of righties lined up for the Yankees. The Sox need to get out of a jam. They turn to one of the most unsung heroes in the second half of this season, and Wyatt Olds shuts New York down.

— Fitzy Mo Peña

Brayan Bello. He has a 2.11 ERA and 1.03 WHIP for Boston over 55 ⅓ innings since being recalled on July 12th, and he is barely talked about in this bullpen. He struggled in his start in Yankee Stadium a year ago, and will get payback here. One of Boston’s starters is bound to go short in their start this week, and Bello will pick up the slack with a strong 2-3 inning stint to bridge the gap to the back of the ‘pen.

— Bob Osgood

2-1, Red Sox, because it’s going to go to three games to give me a heart attack and because I refuse to pick the Yankees.

— Jacob Roy

2-1, Red Sox. I can’t do this two years in a row…

— Keagan Stiefel

We’ve seen so much out of this team. April-June. July-August. September. They can win this in two, even with the Yankees starters. They can be aggressive, look for the home run pitch, bunt, and make the Yankees play defense. Cause chaos. But that act probably can’t win you two straight. 2-1 Red Sox. 

— Mike Carlucci

2-0 Yankees. I have grave concerns about the offense getting muzzled by New York’s pitching, and since the best-of-three Wild Card series went in place in 2022, 11 of the 16 series played have ended in two games. Hopefully I’m wrong.

— Matthew Gross

2-1 Sox. Gotta believe, baby.

— Fitzy Mo Peña

Red Sox 2-1. With Max Fried and his 5.31 career playoff ERA throwing Game 2, and Gerrit Cole’s history against Boston in Game 3, I feel damn good about the Sox chances, even if they lose Game 1.

— Bob Osgood