The Top 5 Questions of the 2026 Cubs Season (Following Opening Day) ...Middle East

Every spring as the regular season creeps closer, a bunch of questions pop up and surround each MLB team.

And while many are answered during Spring Training (i.e., who will be the fifth starter?), other big-picture queries linger into Opening Day and well beyond.

To that end, let’s run through the top questions facing the 2026 Cubs.

There are some short-term questions (some of which we already have some answers to), like: Who will man right field in Seiya Suzuki’s absence? (It was Matt Shaw on Opening Day, though veterans Dylan Carlson and Michael Conforto could also see some time there.)

Other questions (like: Will the Cubs sign any players to contract extensions?) have already been resolved (Pete Crow-Armstrong, Nico Hoerner).

Then there are questions that come with every new season, such as: Will the Cubs stay healthy and be able to weather the injury storm?

[5 bold predictions for the 2026 Cubs season]

There are also other questions that don’t carry the same weight as the topics below, at least in my opinion, like:

How will Shota Imanaga fare in 2026? (I believe he’ll be just fine, and one poor six-week stretch to end 2025 isn’t enough to erase the 1.5 years of strong performance prior.)

Can Dansby Swanson contribute more offensively? (It’s certainly possible, but I don’t think that’s a major storyline right now. If he doesn’t, he still provides stellar defense, and he’s the team’s No. 8 hitter.)

2026 Cubs. It’s here. Let’s go. pic.twitter.com/856kxjTVJY

Instead, these are the five most important questions that I’ve been asking myself all winter and spring.

Top-5 Questions for the 2026 Cubs

5. How does the bullpen shake out?

This isn’t a concern, so much as a genuine wonder about where everybody ends up slotting in and how the Cubs find a way to form an effective relief unit.

They completely remade the bullpen in the offseason after a strong 2025 campaign headlined by Brad Keller, Andrew Kittredge, and Drew Pomeranz. That trio has been replaced by Phil Maton, Jacob Webb, Hunter Harvey, and Hoby Milner.

But even last year’s group was a constant work in progress (as most bullpens are each year). Consider that Ryan Pressly, Julian Merryweather, Eli Morgan, Nate Pearson and Porter Hodge began 2025 as the back end of the bullpen.

Daniel Palencia — who wasn’t even on the Opening Day roster last year — stepped up as the team’s closer early in the season and held the job until a shoulder injury in September. He returned in the playoffs and filled more of a fireman role, often pitching as the first one out of the bullpen in the fifth inning.

This season, he is the closer to start, with Maton and Caleb Thielbar likely serving as the top right-handed and left-handed high-leverage options, respectively. But Webb and Harvey have had success in the past as well, and Milner has a long rapport with Cubs manager Craig Counsell from their Milwaukee days (where Milner posted a 1.82 ERA in 73 games in 2023).

That appears to be the plan right now, with those six arms forming the back end of the bullpen. But I can’t remember the last time the Cubs had a season where almost the entire bullpen was stable and consistent all season. There are always injuries and ineffectiveness leading to a slew of roster moves. That’s just the reality in today’s game with so much strain put onto bullpens.

The other aspect of this relief corps is that only Palencia and Ben Brown have minor league options remaining. Palencia very likely won’t be sent back down, leaving only Brown as the optionable/flexible arm in the bullpen unless an IL stint hits.

Counsell’s coaching staff and Jed Hoyer’s front office have earned the benefit of the doubt when it comes to building a strong bullpen in recent seasons. But it’s impossible to predict how it will all play out in late March or even early April.

4. What kind of season will Edward Cabrera put up in his first year in Chicago?

Alex Bregman was the highest-profile addition over the offseason, but Edward Cabrera carries immense upside and the potential for a huge impact on the Cubs. However, he also comes with legitimate question marks.

Cabrera is entering his sixth MLB season and begins the season as the Cubs’ No. 4 or No. 5 starter (strictly speaking and depending on when they deploy him in the series against the Angels). But he hasn’t quite put it all together yet in the majors.

Cabrera has teased his potential, with a career 10.0 K/9, and has had a couple of seasons with strong results (3.01 ERA in 2022, 3.53 in 2025). At the same time, he has struggled with his control and health — his 137.2 innings last season were a career-high by a wide margin.

Will he stay healthy? Will he keep the walks to a minimum? Will he harness that elite stuff and pitch well in front of the Cubs’ elite defense?

It’s entirely possible that Cabrera enjoys a true breakout campaign in his age-28 season. But it is not a sure thing. He enters the year as the most intriguing pitcher on the roster.

3. Who else will step up?

The Bregman signing was huge and helps mitigate the loss of Kyle Tucker in the offseason. But for the Cubs to get where they want to go (playing deep into October), they will need others to step up.

[The thing you are: An emotional look back at the decade since the Cubs’ 2016 championship]

As Hoyer has mentioned often over his time with the Cubs, teams almost always need some players to outperform expectations in order to contend. Each season brings about some unexpected performances.

Last year, Pete Crow-Armstrong exploded into a superstar in the first half. Michael Busch took a major step forward, Colin Rea was a strong contributor in a swingman role, and we saw Brad Keller and Drew Pomeranz come out of nowhere to serve as key high-leverage relievers.

Who will take a step forward in 2026?

Moisés Ballesteros looks like he could be a quality MLB hitter filling the DH role. I could see Busch taking another step forward (and started strong with three hits and a walk on Opening Day). Offensive improvements from Dansby Swanson and Matt Shaw, plus more consistency from Crow-Armstrong, would go a long way. Imagine what a Cabrera breakout campaign and/or Justin Steele returning to form will do for this starting rotation.

Miguel Amaya is another name to watch. He has shown flashes of being a quality catcher on both sides of the ball, but he has not performed well over a full season and has also been bogged down by injuries. Can one of the veteran bench players (Conforto, Carlson, Scott Kingery) step up when afforded opportunities?

2. When will Justin Steele return, and what will he look like when he’s back?

If he’s the Justin Steele of old — the one who was a Cy Young candidate in 2023 — the Cubs would be in very, very good shape.

If he struggles, it’s a different story. And we’ve seen some pitchers struggle coming off elbow surgery. Atlanta’s Spencer Strider had an internal brace procedure after a previous Tommy John surgery (the same as Steele) and has seen up-and-down results since his return, including with his velocity and overall effectiveness.

We know Steele won’t be back before late-May, as the Cubs placed him on the 60-day IL just before Opening Day. But will he return shortly after he is eligible to come off the IL? How effective will he be? And what kind of workload will he be able to handle after tossing only 22.2 innings last season?

1. What will we see from Pete Crow-Armstrong this season?

This is the top question I had entering for the 2026 Cubs.

Crow-Armstrong has arguably the highest floor on the Cubs roster, as his defense is so elite that he can be an above-average player even if he doesn’t hit at all.

But he also has the highest upside of anybody else on the team. He has the potential to go toe-to-toe with Shohei Ohtani in the NL MVP race (as he did for the first half last season) and post an 8+ WAR season.

To: @ofcwrigleyfield With love, Pete. pic.twitter.com/OVuvw4G46O

The 2026 Cubs have a strong team up and down the roster. But they could use a face of the franchise — a true stud. Crow-Armstrong can be that superstar, and I think he will be. Clearly, the Cubs do too, as they just handed him a contract extension that will pay him an average of $19 million per season for the next six years.

But at least some doubt exists after his poor second half last season offensively (.216/.262/.372, .634 OPS). It’s clear he has some growing still to do in terms of plate discipline, as it’s tough to sustain and repeat his electric first half with that type of approach.

If PCA can put up a more consistent season at the plate and level off some of the streakiness we’ve seen from him in his young career, it will benefit the Cubs greatly.

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