Cubs vs Pirates Preview: Can Chicago Stop the Bleeding?

Chicago Cubs · 2026-09-11 · Beatline Sports Podcast Network

Stephanie: They told you they were going to sweep us. They said the Brewers were too strong, that the bullpen was tapped out, and that the momentum had completely shifted to Milwaukee. Well, look at the scoreboard from Wednesday night. The Brewers completed that three-game sweep with an 8-6 victory, extending their NL Central lead to ten games over the Cubs. It’s a brutal blow to the playoff hopes in Chicago.

Sean: It is tough to watch, Steph. You have a team that played well enough to stay in contention all season, but now they are trailing by double digits with just weeks left. The emotional toll of that sweep, especially after the close calls earlier in the series, is real. But we aren't here to dwell on the past. We are here to look forward.

Stephanie: Exactly. And what is coming next? Today, September 11th, 2026, the Pittsburgh Pirates come into Wrigley Field for a two-game set. Chicago sits second in the NL Central at 81-66, while Pittsburgh is third at 74-73. This is about pride, it’s about building momentum, and frankly, it’s about survival in the race. Welcome to the Beatline Podcast Network!

Sean: Thanks for having me. If today’s breakdown helps you see the tactical shifts happening in Chicago’s rotation or clarifies who is actually healthy in that bullpen, then this episode was worth your time. If you’re enjoying the daily deep dives, please chip in via the link in the episode description. Every bit keeps the show free and daily for fans like us.

Stephanie: That is so appreciated. Alright, let’s get into it. In this episode, we’ll break down the pitching matchups for the Pirates series, analyze which hitters need to step up given the current injury list, and give you our bold predictions for how these next two days end. Let’s dive into Segment One: The Series and the Pitching Probables.

Stephanie: So, Sean, we talked about Shota Imanaga last week. He started Game Two against Milwaukee, and despite his stuff being there, the offense couldn't string together enough runs to support him in those final two losses. Now, the Cubs are home against Pittsburgh. Who do you think starts for Chicago on Friday night?

Sean: Well, looking at the roster provided, Imanaga is still in the mix, but the management might want to rest him slightly after that heavy workload in Milwaukee. However, if I’m the Cubs, I’m going with Kevin Gausman. He’s got the experience, he’s been reliable when called upon, and facing a Pirates lineup that has struggled against high-velocity arms could be exactly the bounce-back game he needs.

Stephanie: Gausman makes sense. But what about Saturday? With the bullpen as depleted as it is, do you trust Colin Rea to go deep into that game, or are you looking at David Peterson stepping up?

Sean: I think you have to be careful with Rea right now. His pitch count matters more than ever. I’d lean toward David Peterson for the second start. He’s a ground-ball guy, which is great for Wrigley Field where the infield dirt can cause tricky hops, but mostly because it preserves the bullpen. If Jacob Webb is available—and remember, he was mentioned in recent episodes as potentially returning—he might need to save his arm for Sunday's closer role, even if it’s a two-day series.

Stephanie: Okay, so Gausman and Peterson. Now, let’s talk Pittsburgh. They’ve brought a win streak into this matchup. Their record is 74-73, third in the division. Who is likely on the mound for them? Do they have anyone who gives Chicago trouble?

Sean: The Pirates have some young arms that are dangerous. If they are riding hot hands, they might send out one of their younger starters to try to keep the streak alive. But historically, Chicago has had success against right-handed pitching early in the season, and if Pittsburgh’s starter is a fly-ball pitcher, the wind at Wrigley could work against them. The key will be whether Chicago can handle the velocity early.

Stephanie: Right. So, no easy outs for the Cubs hitters. If Gausman goes, he needs to get quick strikes. No long innings. Because once the ball is in play, we have to talk about Segment Two: Key Hitters, Bullpen Questions, and Injuries. This is where things get messy for Chicago.

Sean: It is messy. Let’s look at the injury report. Jake Bauers is Day-To-Day. That’s a significant loss for depth. Then you have Bryse Wilson on the 15-Day IL, Grant Anderson on the 15-Day IL, and Gavin Hollowell also on the 15-Day IL. On the longer-term side, Rob Zastryzny, Brandon Woodruff, Tyler Austin, Edward Cabrera, Hunter Harvey, and Shelby Miller are all on the 60-Day IL.

Stephanie: That is a massive list. Brandon Woodruff being out is huge for the league, but for the Cubs, losing Grant Anderson and Bryse Wilson means their middle relief options are severely compromised. How does this impact Alex Bregman and Gabriel Arias at third base? Are they playing through something, or is this purely rotational?

Sean: Bregman and Arias seem healthy, but the concern is the bench. With Bauers Day-To-Day, you don’t have a left-handed bat off the bench easily. This forces the manager to rely heavily on Michael Conforto at DH or Matt Shaw in right field. If Conforto isn’t swinging well, the lineup becomes predictable. The Cubs need Seiya Suzuki and Ian Happ to carry the load in the middle of the order.

Stephanie: Ian Happ has been solid, but his OBP has fluctuated. Do you think the pressure of the late-season slump affects his plate discipline? Or does he tighten up and chase pitches?

Sean: He tends to tighten up when the stakes feel highest. Against a Pirates team on a win streak, Pittsburgh will likely attack the edges. If Happ doesn’t expand his zone, he could draw walks. But if he tries to hit every pitch out of the park, he’ll make outs. The Cubs need patience. They need to work the count. Nico Hoerner at the top of the order sets the tone, but it’s Happ and Conforto who drive the RISP numbers.

Stephanie: And what about the bullpen? We know Jacob Webb was strained recently. Is he ready? And who is closing? Javier Assad, Daniel Palencia, Ryan Rolison, Caleb Thielbar, Trent Thornton, Jacob Webb, Ryan Zeferjahn—that’s a lot of arms, but are any of them trustworthy right now?

Sean: This is the biggest question mark. If Webb is healthy, he’s the best option for high-leverage situations. But if he’s not, you’re looking at Javier Assad or maybe even pulling a starter like Matthew Boyd for a short outing. The risk is immense. A two-run lead in the eighth inning against a Pirates team trying to steal momentum is a coin flip. The Cubs cannot afford to blow leads here.

Stephanie: So, if the bullpen falters, the offense has to score more runs. We saw against Milwaukee that 6 runs wasn’t enough. What does it take to beat Pittsburgh? Do we need a multi-homer game? Or is it about small ball?

Sean: Small ball won’t cut it against a team with momentum. You need big innings. Miguel Amaya and Carson Kelly behind the plate need to frame pitches perfectly to help the starters get through five innings. If the pitchers can keep the game low-scoring early, then the bullpen has a chance. But if it’s a shootout, Chicago’s thin defense might get exposed. Pete Crow-Armstrong in center field has to be alert; one error changes everything.

Stephanie: Alright, we’ve covered the injuries, the pitchers, and the hitters. It’s clear this series is critical. Let’s move to Segment Three: Keys to the Series and Our Bold Predictions. Sean, you predicted a Pirates sweep last time. Are you sticking with that? Or has the home-field advantage changed your mind?

Sean: I’m sticking with my guns, but with less confidence. The Pirates are playing with house money. They’re below .500 but on a win streak. They have nothing to lose. Chicago is carrying the weight of expectation. My prediction? The Pirates split the series. They win one convincingly and lose one by a single run. But I still think they take Game One.

Stephanie: Okay, so Pirates split. But I’m predicting differently. I think the Cubs snap this skid. I think Gausman dominates Game One, and the offense wakes up. I’m going with a Cubs sweep. Why? Because Wrigley Field in September is electric, and the players need to prove they’re still in this race. I think they win both games.

Sean: A sweep would be amazing for morale. But realistically, the bullpen injuries make a sweep difficult. I think the Cubs win Game Two, but lose Game One. So, one each. But hey, if I’m wrong, and the Cubs do sweep, you owe me dinner.

Stephanie: Deal! But I expect that dinner to be paid for by your own wallet, Sean. Look, the takeaway here is simple: The Cubs must protect their lead in the bullpen. If they can get six strong innings from their starters and use Webb or Assad effectively in the seventh and eighth, they win. If they drag their feet, Pittsburgh takes control.

Sean: Agreed. It’s about execution. Plate discipline, defensive positioning, and trusting the relievers. If the Cubs can manage their emotions after the Brewers sweep and focus on the task at hand, they have the talent to win this series. It’s not about the standings anymore; it’s about how they finish the season.

Stephanie: Well, there you have it. The Cubs host the Pirates today. We’re expecting a split, but hoping for a sweep. Make sure to subscribe, rate, and review the Beatline Podcast Network wherever you get your shows. Share this episode with a fellow Cub fan and let’s keep the conversation going. For Sean, I’m Stephanie. Go Cubs!