Red Sox Preview: Can They Beat the Cubs After That Heartbreaker?

Boston Red Sox · 2026-09-25 · Beatline Sports Podcast Network

Melissa: You lost 1-0. You watched Angel Martínez’s homer sail over the wall while Joey Cantillo pitched five one-hit innings against you. And now, less than twenty-four hours later, you’re back on the field to face the Chicago Cubs.

Ryan: It’s a brutal turnaround. One night you’re mourning a shutout loss that costs you momentum, and the next you’re trying to find answers against a division rival. The stakes? High. The roster? Decimated.

Melissa: Welcome to the Beatline Podcast Network. I’m Melissa, and this is your daily preview of the Boston Red Sox. I’m joined by Ryan, who has been tracking every injury report and bullpen usage metric since spring training.

Ryan: Good morning, Boston. If you’re tuning in during your commute or grabbing coffee before work, we’ve got the full breakdown of today’s matchup, the pitching probables, and exactly how this lineup looks with so many guys on the IL.

Melissa: Here is what we are covering today. First, we break down the pitching strategy for the Cubs series—can Sonny Gray carry the load again? Second, we look at the offensive keys with Roman Anthony still riding hot, but Willson Contreras’ status uncertain. And third, we give you our bold prediction for how this series ends.

Ryan: We also address the elephant in the room: the injury list. Houck, Oviedo, Kelly, Yoshida, Hoskins—all gone. It’s a thin rotation, and it’s going to test the depth of this club right when October approaches.

Melissa: Let’s start with the pitching. Yesterday, we talked about how the rotation was depleted. Today, we have Brayan Bello, Jake Bennett, Ray Burgos, Sonny Gray, Patrick Sandoval, and Payton Tolle available. Who do you think starts the first game against Chicago?

Ryan: If I’m Chris Fannin, I’m looking at Sonny Gray. He went ace yesterday against Cleveland. He had the stuff. But managing his pitch count after a high-leverage outing is tricky. Alternatively, Brayan Bello provides stability if they want to save Gray for a potential Game 3 or a Wild Card prep.

Melissa: Gray is an asset, though. You can’t burn him out in September if there’s any chance he needs to go deep into October. But the Cubs aren’t exactly a weak lineup. How does Gray match up against them historically?

Ryan: Gray’s command is elite. His ability to mix off-speed pitches keeps hitters off balance. The Cubs rely on contact, and Gray doesn’t give up easy contact. However, if he gets behind in counts early, that’s where trouble brews. We saw that vulnerability in some earlier starts this year.

Melissa: Right. And if Gray doesn’t go, who is the backup plan? Payton Tolle? Patrick Sandoval? Those are risky bets.

Ryan: Tolle has upside, but consistency is the issue. Sandoval has been more reliable lately, especially with his sinker generating ground balls. Against a team like Chicago, inducing double plays is key. So I’d lean toward Sandoval if they want to preserve Gray’s arm for a late-series appearance.

Melissa: So we’re talking about a heavy reliance on the top three arms, with the bullpen carrying massive innings. Let’s talk about that bullpen. With Whitlock and Holderman dealing with injuries, who is left?

Ryan: Aroldis Chapman is still here. That’s huge. Having a 98-mile-per-hour heater in the ninth gives you a closer option. Then you have Erik Miller, Tyron Guerrero, Jovani Moran, Alec Gamboa, Raymond Burgos, and Greg Weissert. It’s a committee approach.

Melissa: A committee. Which means no single guy can be overworked. If Gray goes six strong, you need four relievers to finish it. That’s a lot of stress on those arms.

Ryan: Exactly. And platoon splits matter here. Some of these relievers struggle against left-handed power. The Cubs have lefty bats. If the manager leans too hard on one side of the bullpen, it could blow up quickly.

Melissa: Stick with us. Next, we dive into the offense, Roman Anthony’s surge, and the big question mark at first base.

Melissa: Roman Anthony. In our previews from Tuesday and Wednesday, we predicted he would continue his offensive surge. Well, he didn’t hit yesterday—Cleveland held him scoreless—but his season stats are undeniable. How important is he to this lineup right now?

Ryan: He’s vital. When Anthony is healthy and in the lineup, the entire offensive structure shifts. His plate discipline forces pitchers to throw strikes. He draws walks, which takes pressure off the middle of the order. Yesterday was an outlier, not the trend.

Melissa: But what about the rest of the lineup? With Rhys Hoskins and Masataka Yoshida on the 10-day IL, the middle order is thin. Who is stepping up?

Ryan: Wilyer Abreu and Jarren Duran are carrying a lot of weight. Abreu’s launch angle has been improving, and Duran’s speed creates chaos on the bases. Even without Hoskins, the Red Sox can generate runs through small ball and timely hitting.

Melissa: And then there’s Willson Contreras. The headlines say he’s uncertain whether he will be available to play when the AL Wild Card Series starts Tuesday. Does that affect today’s decision?

Ryan: Contreras is a veteran presence. If he’s even 80 percent, he provides power from the left side. The Cubs have to respect his pull power. If he sits, Nick Sogard or Caleb Durbin might get more time at first base, but the power drop-off is real.

Melissa: That’s a tough call. Do you push him to play today to keep him loose, or rest him for the potential playoff run?

Ryan: I’d bet on rest. The risk of aggravating whatever injury is holding him back isn’t worth it for a regular-season game against Chicago. Unless he’s feeling great, he stays on the bench. It’s about long-term health.

Melissa: Makes sense. But it leaves a hole in the lineup. Mickey Gasper or Jahmai Jones might see DH duty. Gasper has shown flashes of power, but consistency is key.

Ryan: Gasper is young. This is a good opportunity for him to prove himself. If he can drive in a run or two, it boosts his confidence heading into the postseason. But don’t expect him to be the anchor of the offense yet.

Melissa: Before we move to our final segment, I want to take a quick moment. If these daily breakdowns are part of your morning routine or commute, a small tip is what keeps us coming back with fresh, factual analysis every single day. Please consider supporting the show via the link in the episode description. It helps keep the coverage free and consistent.

Melissa: Alright, let’s get to our final segment. Keys to the series. What does Boston need to do to win this set against the Cubs?

Ryan: Number one: manage the bullpen. Don’t burn out Chapman early. Use the middle relievers strategically. Number two: exploit the Cubs’ starting pitcher. If they go with a weaker starter, attack early. Number three: defense. With so many players injured, positioning is critical.

Melissa: And defensively, Andruw Monasterio and Trevor Story at shortstop need to be sharp. One error can change the game. What’s your bold prediction for this series?

Ryan: I predict the Red Sox split the series. They’ll lose one game due to bullpen fatigue, but win another thanks to Gray or Sandoval dominating. A 1-1 split keeps their playoff hopes alive and preserves energy for October.

Melissa: Bold. I’m going with a sweep. Why? Because the Cubs are inconsistent, and the Red Sox need all the wins they can get for seeding. I think they close out the series 2-0.

Ryan: I’ll take the under on that. The Red Sox are too fragile right now. One bad inning from the bullpen, and the series flips. But I respect the optimism.

Melissa: There you have it. A crucial series against the Cubs, a depleted roster, and Roman Anthony looking to bounce back. Subscribe, rate, and review the Beatline Podcast Network wherever you listen. Go Red Sox!