Offseason Primer: A State of the Union on the Cubs' Bullpen

[Jason Ross]

With the World Series rapidly coming to a close, the offseason is upon us. Despite a looming lockout and the possibility of some lost ballgames, there is a very strong likelihood that the 2027 MLB season will still happen. The Cubs will need to look to build and rebuild, as they hope to not only make the playoffs again next year, but push further. Today, we'll look into the Chicago Cubs' bullpen. We'll recap their 2026 season, take a look at their upcoming roster decisions and then try to map out what the team may attempt to do in what may be a weird, and wacky offseason. 

2026 Recap

The 2026 season wasn't a banner year for the Chicago Cubs' relief corps. After a strong 2025, the North Siders hoped to build upon their success by adding Phil Maton, Justin Webb, Hoby Milner and Hunter Harvey to standouts from the year prior such as Daniel Palencia and Caleb Thielbar. Injuries to Maton, Milner and Harvey cut the legs out from the Cubs' pen, and ineffectiveness from others created a pretty dire situation by mid-season. Attempting to rectify the situation, the team scoured the waiver wire for old friends such as Drew Pomeranz and the trade market, bringing in Angels standout Ryan Zeferjahn in hopes of stabilizing the group. They got mixed results. Ultimately, the team was unable to recreate the success from the year before, and they fell short of their lofty goals for their relievers.

2027 Roster Decisions

• Javier Assad - Team Option - $3.3 million
• Aaron Civale - Free Agent
• Hunter Harvey - Mutual Option - $8 million w/ $1 million buyout
• Colin Rea - Team Option - $7.5 million w/ $1 million buyout
• Caleb Thielbar- Mutual Option - $6 million w/ $500,000 buyout
• Jacob Webb - Team Option - $2.5 million 

Of these decisions, a few are fairly straight forward. Javier Assad's option will be declined, because the team can expect to get him for less than the value of it via arbitration. He'll stick around, though, and he can still be optioned to the minors next year, allowing the Cubs to once again shuttle the pitcher between Iowa and Chicago if need be. He's a lock to be on the team, unless a club is willing to overpay for him in a trade for some reason.

Most of the same can be said for Jacob Webb. As a 7th-inning option, he's great, especially for his price. Picking up his option is an easy call. The Cubs will certainly hope to not have to rely on him as the de facto closer next season, but his August swoon aside, Webb was effective and quite useful for most of the year.

On the flip side, declining their end of the mutual options for Caleb Thielbar and Hunter Harvey will be pretty simple choices. Thielbar's 2026 was a roller coaster, and the team can find other options at cheaper prices. Harvey did Hunter Harvey things, which is to say, he got hurt. Declining his option will also be an easy decision. While the Cubs will be on the hook for both of their buyouts, this will clear considerable prospective salary, which the organization can reinvest in their pitching needs.

Things get a little stickier with Aaron Civale and Colin Rea. Civale, who came over to the Cubs midseason via the Athletics, once again produced for the Cubs. It feels very possible that the two sides find common ground, but with any free agent, it's hard to predict those things. He is probably capable of delivering solid middle relief, but all you need is one team offering the chance to start. I have no doubt the Cubs would like to have Rea back, but the questions become "in what role?" and "how much is there to spend?" He may be a casualty of the budget, or he may return as a swingman, like Assad. 

2027 Outlook

It's probably hard to believe, but the Cubs' bullpen is in a pretty good spot. With returning anchors Palencia, Zeferjahn and Ryan Rolison, they have most of a solid high-leverage group. Assad and Webb would offer two more pieces and build out five roster spots of a potential eight. I'm not sure there has been a starting point this strong for the bullpen over the last handful of years (even if that's a low bar to clear) as we entered the offseason. It will make everyone's job a little easier this offseason not having to fully build from ground up.

Beyond those five, there are a lot of wild cards floating around the team that can be added to the fray. Maton struggled with injury and ineffectiveness last season but has been a trustworthy leverage reliever for a long time. A healthy 2027 would go a long way to building out a strong relief unit. Ben Brown, working his way back from injury, may require a permanent home in the pen to avoid the string of injuries that have befallen him. If that happens, he would be another power righty to add to the leverage cocktail.

Edward Cabrera, last year's big trade acquisition, will be given another shot in the rotation, but if he has a 2027 much like his 2026, he may end up working in relief. The team would certainly like to get more out of him, but his pure stuff makes working out of the pen a viable fallback. While that wouldn't be the goal, it would still offer a way to get value out of the righty. Don't sleep on Riley Martin, either. Martin probably has an inside track as the second lefty for next season, as he looked effective in limited action as a rookie. Any or all of these pitchers can provide support and depth, and it wouldn't be surprising to see any of them contribute in strong ways.

The farm is where things get a little less rosy. Jaxon Wiggins may play a role here, but his 2026 was marred with poor performance, rust and diminished velocity, so he's no guarantee. A few right-handed arms (such as Grant Kipp and Kohl Franklin) may provide some mid-innings options, but neither looks like a game changer. Behind that group, you're mostly hoping for pop-up prospects. Much of the pitching that is exciting is too far away to count on next year.

What Might the Team Add to the Mix?

The best reliever on the free-market is left-handed stud Adrian Morejon of the San Diego Padres. Morejon is a beast, but I wouldn't expect him to be on the Cubs' radar. There's a chance the team sees him as a possible flip to the rotation, but unless Tom Ricketts has decided to go to another level on spending, it seems unlikely they will have enough money to fix everything else and splurge on the best reliever available. As fun as building out a bona fide bullpen of death would be, it doesn't seem like it's in the cards (or budget).

Instead, the team will probably try to find quality via quantity and risk-taking. Webb, for example, was a cheap and effective addition last season, and Brad Keller worked out even better in 2025, so look for the team to try and recreate that success. They may look to add a reliever off a down season (Bryan Abreu, for example, could represent a buy-low candidate), as well. I wouldn't get attached to any specific name, but based on recent history, the team finding one or two reclamations who become solidified in the bullpen is a very possible.

General Outlook

The Cubs' don't have a truly difficult pathway to building out a solid bullpen. There won't be a Mason Miller lock-down star, but there's likely to be enough here that the pen should be pretty good. They don't require massive additions and can attempt to fill this out on the cheap, while they spend more on the rotation and the outfield. 

---

What do you think of the Cubs' outlook for the 2027 bullpen? Who would you like to see added? Sound off in the comment section below!

Image courtesy of Matt Marton-Imagn Images

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[Rcal10]

1 hour ago, Jason Ross said:

With the World Series rapidly coming to a close, the offseason is upon us. Despite a looming lockout and the possibility of some lost ballgames, there is a very strong likelihood that the 2027 MLB season will still happen. The Cubs will need to look to build and rebuild, as they hope to not only make the playoffs again next year, but push further. Today, we'll look into the Chicago Cubs' bullpen. We'll recap their 2026 season, take a look at their upcoming roster decisions and then try to map out what the team may attempt to do in what may be a weird, and wacky offseason. 

2026 Recap

The 2026 season wasn't a banner year for the Chicago Cubs' relief corps. After a strong 2025, the North Siders hoped to build upon their success by adding Phil Maton, Justin Webb, Hoby Milner and Hunter Harvey to standouts from the year prior such as Daniel Palencia and Caleb Thielbar. Injuries to Maton, Milner and Harvey cut the legs out from the Cubs' pen, and ineffectiveness from others created a pretty dire situation by mid-season. Attempting to rectify the situation, the team scoured the waiver wire for old friends such as Drew Pomeranz and the trade market, bringing in Angels standout Ryan Zeferjahn in hopes of stabilizing the group. They got mixed results. Ultimately, the team was unable to recreate the success from the year before, and they fell short of their lofty goals for their relievers.

2027 Roster Decisions

• Javier Assad - Team Option - $3.3 million
• Aaron Civale - Free Agent
• Hunter Harvey - Mutual Option - $8 million w/ $1 million buyout
• Colin Rea - Team Option - $7.5 million w/ $1 million buyout
• Caleb Thielbar- Mutual Option - $6 million w/ $500,000 buyout
• Jacob Webb - Team Option - $2.5 million 

Of these decisions, a few are fairly straight forward. Javier Assad's option will be declined, because the team can expect to get him for less than the value of it via arbitration. He'll stick around, though, and he can still be optioned to the minors next year, allowing the Cubs to once again shuttle the pitcher between Iowa and Chicago if need be. He's a lock to be on the team, unless a club is willing to overpay for him in a trade for some reason.

Most of the same can be said for Jacob Webb. As a 7th-inning option, he's great, especially for his price. Picking up his option is an easy call. The Cubs will certainly hope to not have to rely on him as the de facto closer next season, but his August swoon aside, Webb was effective and quite useful for most of the year.

On the flip side, declining their end of the mutual options for Caleb Thielbar and Hunter Harvey will be pretty simple choices. Thielbar's 2026 was a roller coaster, and the team can find other options at cheaper prices. Harvey did Hunter Harvey things, which is to say, he got hurt. Declining his option will also be an easy decision. While the Cubs will be on the hook for both of their buyouts, this will clear considerable prospective salary, which the organization can reinvest in their pitching needs.

Things get a little stickier with Aaron Civale and Colin Rea. Civale, who came over to the Cubs midseason via the Athletics, once again produced for the Cubs. It feels very possible that the two sides find common ground, but with any free agent, it's hard to predict those things. He is probably capable of delivering solid middle relief, but all you need is one team offering the chance to start. I have no doubt the Cubs would like to have Rea back, but the questions become "in what role?" and "how much is there to spend?" He may be a casualty of the budget, or he may return as a swingman, like Assad. 

2027 Outlook

It's probably hard to believe, but the Cubs' bullpen is in a pretty good spot. With returning anchors Palencia, Zeferjahn and Ryan Rolison, they have most of a solid high-leverage group. Assad and Webb would offer two more pieces and build out five roster spots of a potential eight. I'm not sure there has been a starting point this strong for the bullpen over the last handful of years (even if that's a low bar to clear) as we entered the offseason. It will make everyone's job a little easier this offseason not having to fully build from ground up.

Beyond those five, there are a lot of wild cards floating around the team that can be added to the fray. Maton struggled with injury and ineffectiveness last season but has been a trustworthy leverage reliever for a long time. A healthy 2027 would go a long way to building out a strong relief unit. Ben Brown, working his way back from injury, may require a permanent home in the pen to avoid the string of injuries that have befallen him. If that happens, he would be another power righty to add to the leverage cocktail.

Edward Cabrera, last year's big trade acquisition, will be given another shot in the rotation, but if he has a 2027 much like his 2026, he may end up working in relief. The team would certainly like to get more out of him, but his pure stuff makes working out of the pen a viable fallback. While that wouldn't be the goal, it would still offer a way to get value out of the righty. Don't sleep on Riley Martin, either. Martin probably has an inside track as the second lefty for next season, as he looked effective in limited action as a rookie. Any or all of these pitchers can provide support and depth, and it wouldn't be surprising to see any of them contribute in strong ways.

The farm is where things get a little less rosy. Jaxon Wiggins may play a role here, but his 2026 was marred with poor performance, rust and diminished velocity, so he's no guarantee. A few right-handed arms (such as Grant Kipp and Kohl Franklin) may provide some mid-innings options, but neither looks like a game changer. Behind that group, you're mostly hoping for pop-up prospects. Much of the pitching that is exciting is too far away to count on next year.

What Might the Team Add to the Mix?

The best reliever on the free-market is left-handed stud Adrian Morejon of the San Diego Padres. Morejon is a beast, but I wouldn't expect him to be on the Cubs' radar. There's a chance the team sees him as a possible flip to the rotation, but unless Tom Ricketts has decided to go to another level on spending, it seems unlikely they will have enough money to fix everything else and splurge on the best reliever available. As fun as building out a bona fide bullpen of death would be, it doesn't seem like it's in the cards (or budget).

Instead, the team will probably try to find quality via quantity and risk-taking. Webb, for example, was a cheap and effective addition last season, and Brad Keller worked out even better in 2025, so look for the team to try and recreate that success. They may look to add a reliever off a down season (Bryan Abreu, for example, could represent a buy-low candidate), as well. I wouldn't get attached to any specific name, but based on recent history, the team finding one or two reclamations who become solidified in the bullpen is a very possible.

General Outlook

The Cubs' don't have a truly difficult pathway to building out a solid bullpen. There won't be a Mason Miller lock-down star, but there's likely to be enough here that the pen should be pretty good. They don't require massive additions and can attempt to fill this out on the cheap, while they spend more on the rotation and the outfield. 

---

What do you think of the Cubs' outlook for the 2027 bullpen? Who would you like to see added? Sound off in the comment section below!

Image courtesy of Matt Marton-Imagn Images

 

View full article

 

Did you forget Shelby Miller, or is he no longer with the team? Or, it is early in Az, maybe I missed him?🤷

[Jason Ross]

16 minutes ago, Rcal10 said:

Did you forget Shelby Miller, or is he no longer with the team? Or, it is early in Az, maybe I missed him?🤷

He's contracted in 2027. I also didn't mention Gavin Hollowell, Braxton Garrett, Jayden Murray and others who may feature in the pen. This wasn't an exhaustive look at everyone's roles but a general Offseason Primer of where things mostly sit, who's time might be up due to contractual reasons and what I'd expect moving forward. 

[Rcal10]

23 minutes ago, Jason Ross said:

He's contracted in 2027. I also didn't mention Gavin Hollowell, Braxton Garrett, Jayden Murray and others who may feature in the pen. This wasn't an exhaustive look at everyone's roles but a general Offseason Primer of where things mostly sit, who's time might be up due to contractual reasons and what I'd expect moving forward. 

Fair enough. I guess I may be counting on him more than I should. Which would be why I noticed him not listed but not the other guys. Of the other 3, I would say I should have noticed Garrett not listed. Hollowell was never a consideration of mine and I don’t even know who Jayden Murray is. 

[Jason Ross]

7 minutes ago, Rcal10 said:

Fair enough. I guess I may be counting on him more than I should. Which would be why I noticed him not listed but not the other guys. Of the other 3, I would say I should have noticed Garrett not listed. Hollowell was never a consideration of mine and I don’t even know who Jayden Murray is. 

Miller probably plays a role, yeah. I like him. He's cheap and the stuff looked good in Iowa last year even if the results suggested rust. 

[Rcal10]

5 minutes ago, Jason Ross said:

Miller probably plays a role, yeah. I like him. He's cheap and the stuff looked good in Iowa last year even if the results suggested rust. 

That would be great if Miller did have a role. I am counting on him, which is why I really don’t think they do much with the pen this off season. I have Palencia, Zeferjohn, Rolison, Miller and Webb along with guys like Garrett, Brown (if neither is in the rotation) and then guys like Maton (if he is healthy) Assad and Civale. I am encouraged by your opinion of roles Martin too.
I don’t look forward to the idea of Cabrera in the pen. But that is because I hope he is starting and pitching well there. Honestly, this is probably the most set the pen has been in going into the off season as any year Jed has been in charge. I’m not even talking about Wiggins or Hollowell and maybe even Horton by the ASB. I still hope Brown is in the rotation, but if he is in the pen the pen has a chance to be very good. 

[Bertz]

One thing I'm growing to appreciate is that the difference between a late inning reliever and a matchup guy is super thin.  The bulk of relievers are consistent matchup options, but how much you can trust them against opposite handed hitters is a fleeting streaks and slumps situation.

Palencia, Zef, and Webb are three good pitchers I'd generally be comfortable have closing games.  It doesn't take a far left tail outcome for them to be demoted to matchup guy, but they should be a good foundation.  

Miller, Maton, and Rolison are probably good matchup guys, and the former two have shown some potential to be more.  I think this is a solid enough middle relief group even if I don't love Maton's salary

I suspect we'll run two long relievers? The SP depth is too thin to just raw dog it with 5 SPs and what's at Iowa.  Garret and then either Cabrera or a FA like Civale?

There's some solid depth at Iowa too.  Ferguson was very good in a matchup role.  Riley Martin looked great before he got hurt.  Porter Hodge should be back early in the year.  The Iowa SPs too even if you're bearish on them as SPs are probably nice relievers.

I'd be hard pressed to do anything big in the bullpen.  Do your typical waiver claims, sign an injury rehab guy (Harvey?) or two, or maybe trade Kevin Alcantara for his RP equivalent.  But there's no reason to put money here that could go to starting pitching or the outfield.  

[macarthur31]

Great writeup.  It confirms for me that the Cubs have a decent floor at this position.  They also appear to save about $12.5M if they let Thielbar and Harvey walk.  Man, it'd be nice to convert that plus a chunk to lock down Morejon just to make this as "stress free" as possible walking in to '27, but at least 2 SP, 2 Corner OFs and a Catcher to figure out - I just don't see it.

Also, Jed's usual MO is to wait out the market, so unsure how that's gonna work with the impending lockout.  My instinct suggests that the elite FA class (which I'd put Morejon in ) wants to get sorted out so they don't have a situation where they're rushing their ramp up in a likely compressed spring training/start of season scenario (at this point, my mental model is that we'll have 150ish games next season).

Then again, Scott Boras is really good at playing the waiting game himself (killing time with pun-driven pressers), so Tarik Skubal, Seiya Suzuki, and Ryan Jeffers - pull up a chair.

[Named After Maddux]

Good stuff here @Jason Ross. I'd echo the other thoughts it feels like Miller there is some optimism in him taking a late inning role for next year, but also can't feel too comfy with injury history. 

Personally I think there's one clearcut MLB roster add. Just sitting here right now I'd guess a small trade for Garrett Cleavinger. 

Will still bet on a bunch of MiLB signings and optional relievers via waivers and signings.

But a pen entering spring training with something like:
High Leverage: Palencia, Zef, Brown, Miller
Matchup arms:
LHP - Rolison (LHP), Cleavinger (Velo/LHP)
RHP - Webb (vs LHP), Maton (vs RHP CT/sweep)
Long relief options:  one of Assad, Garrett, Wiggins(?) 

Nine players for 8 spots gives you a pretty solid group to start with some wiggle room. With Wiggins I'd keep him starting but it's a possibility he breaks into the bigs in this type of role at some point. And for Brown I'm just not positive he can handle starting but I understand having him at least prepare this winter to start. It gives him an easier path to be a two inning guy early in the year. Maton was a complete flop this year. If it continues I think they move on early, but I'm strangely somewhat optimistic on him after finally addressing that knee with surgery. Just get a solid arm that can bury hitters who struggle with low angle cut/sweep.

[Jason Ross]

2 hours ago, Bertz said:

One thing I'm growing to appreciate is that the difference between a late inning reliever and a matchup guy is super thin.  The bulk of relievers are consistent matchup options, but how much you can trust them against opposite handed hitters is a fleeting streaks and slumps situation.

Palencia, Zef, and Webb are three good pitchers I'd generally be comfortable have closing games.  It doesn't take a far left tail outcome for them to be demoted to matchup guy, but they should be a good foundation.  

Miller, Maton, and Rolison are probably good matchup guys, and the former two have shown some potential to be more.  I think this is a solid enough middle relief group even if I don't love Maton's salary

I suspect we'll run two long relievers? The SP depth is too thin to just raw dog it with 5 SPs and what's at Iowa.  Garret and then either Cabrera or a FA like Civale?

There's some solid depth at Iowa too.  Ferguson was very good in a matchup role.  Riley Martin looked great before he got hurt.  Porter Hodge should be back early in the year.  The Iowa SPs too even if you're bearish on them as SPs are probably nice relievers.

I'd be hard pressed to do anything big in the bullpen.  Do your typical waiver claims, sign an injury rehab guy (Harvey?) or two, or maybe trade Kevin Alcantara for his RP equivalent.  But there's no reason to put money here that could go to starting pitching or the outfield.  

I love the point about the line between leverage and matchup guys and think that's a good thing to keep in mind. Especially with the volatility of relievers, 

Jacob Webb was mostly brought in to be a Mark Leiter Jr type: RHP who gets LHH out. By mid year he's your leverage guy and by the end of the year he's a matchup guy again. 

Give me more Jacob Webbs.

[Jason Ross]

2 hours ago, macarthur31 said:

Great writeup.  It confirms for me that the Cubs have a decent floor at this position.  They also appear to save about $12.5M if they let Thielbar and Harvey walk.  Man, it'd be nice to convert that plus a chunk to lock down Morejon just to make this as "stress free" as possible walking in to '27, but at least 2 SP, 2 Corner OFs and a Catcher to figure out - I just don't see it.

Also, Jed's usual MO is to wait out the market, so unsure how that's gonna work with the impending lockout.  My instinct suggests that the elite FA class (which I'd put Morejon in ) wants to get sorted out so they don't have a situation where they're rushing their ramp up in a likely compressed spring training/start of season scenario (at this point, my mental model is that we'll have 150ish games next season).

Then again, Scott Boras is really good at playing the waiting game himself (killing time with pun-driven pressers), so Tarik Skubal, Seiya Suzuki, and Ryan Jeffers - pull up a chair.

One thing that Jed loves is a deadline. I want to lean to the side that this offseason will be good for him because there will be multiple "deadlines": in December on the start of the lockout and again with ST. I think it'll work in his favor. He does tend to wait things out, but with deadlines I think that's his strong suit.

[Jason Ross]

1 hour ago, Named After Maddux said:

Good stuff here @Jason Ross. I'd echo the other thoughts it feels like Miller there is some optimism in him taking a late inning role for next year, but also can't feel too comfy with injury history. 

Personally I think there's one clearcut MLB roster add. Just sitting here right now I'd guess a small trade for Garrett Cleavinger. 

Will still bet on a bunch of MiLB signings and optional relievers via waivers and signings.

But a pen entering spring training with something like:
High Leverage: Palencia, Zef, Brown, Miller
Matchup arms:
LHP - Rolison (LHP), Cleavinger (Velo/LHP)
RHP - Webb (vs LHP), Maton (vs RHP CT/sweep)
Long relief options:  one of Assad, Garrett, Wiggins(?) 

Nine players for 8 spots gives you a pretty solid group to start with some wiggle room. With Wiggins I'd keep him starting but it's a possibility he breaks into the bigs in this type of role at some point. And for Brown I'm just not positive he can handle starting but I understand having him at least prepare this winter to start. It gives him an easier path to be a two inning guy early in the year. Maton was a complete flop this year. If it continues I think they move on early, but I'm strangely somewhat optimistic on him after finally addressing that knee with surgery. Just get a solid arm that can bury hitters who struggle with low angle cut/sweep.

It took me a few moments because my first thought was "Mike Clevenger is a piece of horsefeathers" and then I realized there's an A in there and Garrett Cleavenger is like super fun to add. One thing the team just hasn't really had is a LHP who pumps velo. Luke Little could for a hot second, but it'd be great to move away a little bit from the Thielbar lefty to a "here's some LHP velo". 

[macarthur31]

28 minutes ago, Jason Ross said:

One thing that Jed loves is a deadline. I want to lean to the side that this offseason will be good for him because there will be multiple "deadlines": in December on the start of the lockout and again with ST. I think it'll work in his favor. He does tend to wait things out, but with deadlines I think that's his strong suit.

Ran into this reddit post that was referring to an Athletic article from about a week ago, which may also be well-placed Scott Boras propaganda, but offers up the December deadline as the one to watch with regards to the big free agents.

While he may not execute the moves that most of us would want (Ohtani, Yamamoto, etc), he does make bold ones (Dansby,Tucker trade, Bregman) as well as opportunistic gambles (Suzuki, Imanaga, Stroman).  I, too, am hopeful he'll make at least one big-ticket move ahead of December 1.

[Jason Ross]

2 minutes ago, macarthur31 said:

Ran into this reddit post that was referring to an Athletic article from about a week ago, which may also be well-placed Scott Boras propaganda, but offers up the December deadline as the one to watch with regards to the big free agents.

While he may not execute the moves that most of us would want (Ohtani, Yamamoto, etc), he does make bold ones (Dansby,Tucker trade, Bregman) as well as opportunistic gambles (Suzuki, Imanaga, Stroman).  I, too, am hopeful he'll make at least one big-ticket move ahead of December 1.

I actually think he did a decent job on Ohtani for all things considered. It sounds like they offered him as much real-world money as the Dodgers even if the Dodgers number sounded bigger with deferrals. Yamamoto was someone I was pounding the ground for but others have some skepticism on. Bummer there. 

Mostly I like Jed. I hope this offseason is a good one for him; and I tend to think he can find some exploits here. Reports today, for example, are that the Dodgers probably won't go bonkers for Skubal. Cubs having a working relationship with Boras might help here.