Let's Triage Chicago Cubs Trade Deadline Needs

[Matthew Trueblood]

Image courtesy of © Brad Rempel-Imagn Images

It's never a bad thing to enter the All-Star break in first place in one's division, and that's where the Cubs are this week. They had to scramble for two straight wins in New York to stay ahead of the Milwaukee Brewers over the weekend, but they managed that, and they get a chance to reset the odometers on some of their higher-mileage players with four days off before they resume play Friday afternoon against the Boston Red Sox. They're clear sellers in good position to make the postseason.

On the other hand, by now, it should be clear to all involved that this team is not a juggernaut. Unlike past years (when, for instance, the Dodgers routinely won 105 or more games), there might not be a juggernaut on the major-league landscape this summer, but if there is one, it's not the Cubs. Some version of this team—with Seiya Suzuki's power exploding onto the scene the way it has; Pete Crow-Armstrong enjoying the biggest star turn in the big leagues; and Matthew Boyd staying both healthy and excellent to date—might have cruised to a division title, but that version of the team also would have needed Ian Happ and Matt Shaw to be consistently productive and their top three starters (Justin Steele, Shota Imanaga and Jameson Taillon) to rack up healthy innings.

As things stand, the fight for the NL Central will be a brawl settled only in the final week, and any deep playoff run depends not only on winning that fight, but on getting reinforcements between now and then to deepen multiple thin places on the roster. The Cubs started 38-22; they're just 19-17 since. A fairly soft schedule should give them room for error over the final two months, but they have to earn that by getting better, too. They have needs in all four key demographics of the roster—rotation, bullpen, lineup, and bench—and beyond. Let's rank those needs, from most dire to most manageable, so we know where to direct the bulk of our energy and attention in the fortnight to come.

1. Starting Pitching
Few fan bases love to nitpick the notion of a playoff-caliber starter more than Cubs fans—which is particularly odd, given that the Cubs are not a team who routinely even makes it to October. The idea that anyone should feel nervous about giving the ball to Imanaga or Boyd because of their lack of overpowering sheer stuff, or to Cade Horton because of his lack of experience, is foolish. Still, this comes in as the top need for the team, and it's not even especially close.

One reason is obvious: the Brewers are mounting a serious challenge, there's a long stretch without off days coming for the team in August, and the Cubs can't afford to be short on rotation depth. Ideally, they would go to a six-man rotation for a good chunk of the second half. Right now, that's a logistical nightmare even in concept. In practice, it would be impossible. They need at least one good buttress at the back end of the rotation, and they would do very well to acquire two capable starters, one of whom is more of a frontline arm. Ideally, that pitcher would have team control beyond this year, since it's not at all clear that the team will be able to count on more innings from Boyd, Imanaga, Taillon and Steele in 2026 than they're getting in 2025.

Of course, what I'm describing is wildly expensive. The team could use two good starters, and might even want to get that done, but there's virtually no chance that they will, because they have other needs to fill. Craig Counsell will, in all likelihood, have to settle for one new arm and hope it's of the higher-echelon variety—or at least that whoever it is can take the ball whenever injury or exhaustion catches up to Boyd or Horton.

2. Relief Pitching
For the umpteenth year in a row, Jed Hoyer has proved that he knows where to look to cobble together a solid relief corps from scrapheap scoop-ups and under-the-radar homegrown hurlers, even after Opening Day. You remember Tyson Miller and Jorge López from 2024, and Michael Fulmer and Julien Merryweather from 2023, but it goes back much farther than that. This year, it's been not only offseason additions Caleb Thielbar and Brad Keller, but on-the-run minor-league acquisitions Drew Pomeranz and Chris Flexen. 

The thing is, that particular brand of bullpen magic doesn't even last a full season. Fulmer got hurt. López got hurt. Adbert Alzolay wore down at just the wrong moment in 2023. The cracks are already showing in this year's group, and even where cracks aren't showing, they're forming. The cumulative age of Ryan Pressly, Ryan Brasier, Thielbar and Pomeranz (147) is greater than the length of time since the mound moved back to 60 feet, 6 inches. As good as they've been, at times, they're all significant risks for injury. Keller and Flexen, meanwhile, are candidates for significant regression, even after we acknowledge that Keller's stuff has ticked up tremendously after his winter transformation and a spring transition to the bullpen.

With Daniel Palencia anchoring the unit, the temptation to slide this need further down the board is there, but it's important to resist it. The Cubs need bullpen help, if they want to hold enough leads to get to the finish line in front of the pack in the Central. They just can't afford to pay much for it.

3. A Competent Third Baseman
This is where the real trouble starts, because in July, it's never your top need that derails you. You can address that, even if it ends up feeling like a watery solution. It's when you get this far down the checklist and you still feel like the need is pressing that there's a real problem afoot, and that's the case right now in Chicago.

Matt Shaw was probably overrated by prospect hounds this offseason. In fairness to the Cubs, they seemed to know that even coming in; that's why they bid heavily for Alex Bregman. In the end, though, neither the front office nor ownership were willing to flex on the structure of their offer enough to entice Bregman to choose them over the Red Sox, and they're paying a dear price for that now. Shaw might yet turn into a good big-league player—there's plenty of reason to worry about that, but it's far too early to rule out the possibility—but he's not ready to be that kind of player yet. The team needs to upgrade that position, because they're not getting enough offense from second base or left field to stomach a .556 OPS at the hot corner. Nor does Shaw look ready to turn the corner.

Unfortunately, this might just not be in the cards. The Cubs have traded for third basemen at each of the last two deadlines, and Hoyer's track record with those moves is brutal. Shaw is almost exactly the player Nick Madrigal was two years ago, when the team traded for Jeimer Candelario to rotate Madrigal out of the spot—but Candelario played so poorly that the team often ended up sticking with Madrigal and his stellar glove, anyway. That was when they had a healthy Steele, Taillon, and even Marcus Stroman; they didn't need to go make a splash on the pitching side. Now, they have a thinning farm system and two more pressing needs. Shaw might just have to keep sucking up precious outs at the bottom of the batting order, because the team can't afford to replace him.

4. A Bench Overhaul
If anything, Hoyer's track record with building or upgrading the bench is even worse than that with trades for third basemen in July. The team is barely out of the shadow of the Trey Mancini and Tucker Barnhart calamities, and they're staring at a bench that has managed to be even more dysfunctional: Justin Turner, Jon Berti and Vidal Bruján have been a combined 11 runs worse than average, according to Baseball Reference, even as Craig Counsell has done everything in his power to limit their playing time. You can't truly hide players on benches as shallow as those run by every big-league team, at this point, and the Cubs need players their manager feels less compelled to hide.

The good news here is that checking this box should be easy. It's hard to find a frontline starter, an ace reliever or a solid third baseman whose team is willing to trade them at this time of year. It's relatively easy to be a more useful player than Berti has been this season. Throwing a little money at the problem might help; plenty of bad teams are looking to get a few million dollars cheaper as they slog toward the end of lost seasons. The Cubs have room to absorb some money and acquire a good bench piece without giving up much talent.

5. Organizational Depth at Both Ends of the Battery
This feels like a mere bonus item, but it's not. The Cubs are too thin at the upper reaches of their farm system, in terms of reliable, big-league-caliber pitchers and catchers. That could bite them even down the stretch, but it's a problem that will linger into the offseason, too. They should try to find an optionable arm or two and a castoff or blocked catcher whom they can snatch up cheaply, to head off this issue before it becomes a truly glaring problem at a terrible time. 

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There's good news about all of these needs: the Cubs are proving to be very good at coaching players at the big-league level. Suzuki, Crow-Armstrong, Carson Kelly and others demonstrate the team's savvy with hitters, who have tapped into more power under the team's coaching infrastructure this year. Tommy Hottovy is widely respected throughout the game for his work with pitchers, and Boyd, Colin Rea and Keller are just a few of his success stories this year, alone. Quintin Berry and Jose Javier have them running the bases as well as any team in baseball and positioning themselves quite well afield. Counsell's coaching staff is doing its thing. That means that, for instance, one should hold out some real hope for a player like Ryan McMahon, should the team acquire him to stop the gap at third base. Chris Paddack of the Twins is a good candidate to be that secondary starting pitching acquisition, using money more than prospect capital, and he would do well under Hottovy.

However, these needs are real, and they've shown up on the field recently. The Cubs have the lead, but the Brewers have the momentum in the race for the Central division crown—and if you don't believe in that kind of thing, then substitute 'depth' for 'momentum'. It comes to the same thing. The Brewers also have a deeper farm system, which gives them more ways to improve between now and the end of the season than the Cubs have. That's why it's important for Chicago to nail this deadline, by knowing how to order their priorities and where to allocate their resources.

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[Bertz]

I think you're right that opportunity cost is high enough that it might not happen, but I do think two starting pitcher is both #1 and #2 on the priority list.  And this is coming from someone who is still *very* high on Brown.  But as we're obviously seeing the team is not a lot of misfortune removed from giving starts to Chris Flexen, and that's before the load management conversations around Horton/Brown/Boyd really come to a head. 

Two SPs also has the benefit of potentially impacting the bullpen depth.  Giving Horton 3 more starts and then downshifting him to short relief is probably a great two birds/one stone move for managing his innings (he'd probably end the year right around 120?) and adding an arm with some oomph to the late inning mix.  That's not to say if you can add two SPs it's safe to ignore the bullpen.  But if you add two SPs you can shop in the Kyle Finnegan section of the store rather than the David Bednar aisle.

On the position player side, I hope the Twins start fading again because Willi Castro is a glove perfect fit for this roster.  I'm not especially worried about Shaw (there's a healthy amount of BABIP regression coming his way), but you can't not address 3B at all.  Castro would provide some 3B production, but also provide some support everywhere in case of injury.  Like god forbid a middle infielder especially gets hurt right now.

[Tryptamine]

I'm where I was a few weeks ago. An at least mid rotation starter who you can actually have make a playoff start is a must. Behind that I have a 3B bat, not necessarily a full time 3B but a bat who can play 3B if need be. 3rd on the list I'm split between a nice solid back of the rotation inning eating SP like Charlie Morton or a true closer/elite set up man. I'm not entirely convinced the pen is a major need, especially with Horton and Brown probably headed there in the not to distant future, but if you can get a really elite arm then by all means. At this point with Ryan seemingly off the table and Cabrera being hurt, I'd be all in on either Kelly or Lugo. Snag Charlie Morton and Willi Castro and call it a deadline.

[CubUgly]

1. Starting Pitching
Few fan bases love to nitpick the notion of a playoff-caliber starter more than Cubs fans—which is particularly odd, given that the Cubs are not a team who routinely even makes it to October. The idea that anyone should feel nervous about giving the ball to Imanaga or Boyd because of their lack of overpowering sheer stuff, or to Cade Horton because of his lack of experience, is foolish. Still, this comes in as the top need for the team, and it's not even especially close.

 

My main concern is not how good Boyd is, it's whether or not he'll still be pitching in October given that he hasn't pitched over 100 innings in 6 years.  And I can't get past it.   It's not that I'm nervous giving him the ball, I'm nervous about whether not he'll be around to give the ball too. 

[Rcal10]

2 hours ago, Tryptamine said:

I'm where I was a few weeks ago. An at least mid rotation starter who you can actually have make a playoff start is a must. Behind that I have a 3B bat, not necessarily a full time 3B but a bat who can play 3B if need be. 3rd on the list I'm split between a nice solid back of the rotation inning eating SP like Charlie Morton or a true closer/elite set up man. I'm not entirely convinced the pen is a major need, especially with Horton and Brown probably headed there in the not to distant future, but if you can get a really elite arm then by all means. At this point with Ryan seemingly off the table and Cabrera being hurt, I'd be all in on either Kelly or Lugo. Snag Charlie Morton and Willi Castro and call it a deadline.

If they are not interested in moving any of their top 5 prospects in deals to improve the team I am more than happy with your scenerio. But, I would rather go big and get Gore and than add any of their 3 pitchers you mentioned. He will be very expensive. I also like the idea of Castro. Again, he shouldn’t cost a top 8 guy in the system. I think adding two right handed starters to Boyd, Imanaga and Tailon(eventually) would make their rotation 5 deep with a decent chance to win any game. The pen also gets better with Horton and even Rea going to the pen. But, damn, Gore(or Ryan) really improved the rotation. Just a matter of who they need to give up. I think to get Gore the nats would probably get their pick of any 3 prospects in the minors. Tough ask, but Gore is pretty special and still has years of control. 

[JunkyardWalrus]

Gore is someone I’d be willing to move Cassie, J-Wiggles, or Rojas for. Nothing less, and not all three. 

[Jeff Alson]

Gore would require at least 3 of the top 5 Cubs prospects, and probably more. I don't think the Nats want to trade him, and I don't want to destroy our farm system to get him.

I used to think a starting pitcher was our top priority, but I have changed my mind, I think it is a right handed hitting 3B. Swanson has often batted 4th against lefties and 5th or 6th against righties, and while he has had a decent overall year, he is a weak hitter to be batting in those key spots for a playoff team, especially with his poor hitting with RISP. We need at least an average hitting righty 3B and then Counsell can choose between him, Swanson, Kelly, Amaya, and Hoerner for the key righty spots, depending on which players are hot.

In the playoffs, with all the off days, most teams only use 3 starting pitchers all the time, and occasionally a 4th starter. Boyd and Imanaga are obviously our top two, and Taillon, Rea, Horton, and Brown give Counsell a group to choose from depending on healty and effectiveness, or the depth to go with a bullpen game, which some teams have been doing in the playoffs. Going all in for "top 3" starting pitcher would destroy our farm system, and going for an "innings eater" starter wouldn't change our odds much in the playoffs.

With Steele out, we can't match the starting pitching of the Dodgers or Phillies or most of the other NL playoff teams, so instead I would rather focus on a deep offensive lineup, a great defense, and good base running. I believe a righty 3B and a good reliever with playoff experience would maximize our chances in the playoffs while maintaining most of our top prospects.

 

[CubUgly]

9 hours ago, Jeff Alson said:

Boyd and Imanaga are obviously our top two, and Taillon, Rea, Horton, and Brown give Counsell a group to choose from depending on healty and effectiveness, or the depth to go with a bullpen game, which some teams have been doing in the playoffs. Going all in for "top 3" starting pitcher would destroy our farm system, and going for an "innings eater" starter wouldn't change our odds much in the playoffs.

 

 

Again, will Boyd still be pitching in October.  For me that's a very legit if and has to be considered and a very good possibility he will not.  If we do not proceed with that in mind, it would be a big mistake IMHO.

 

Horton too for that matter. 

[Rcal10]

11 hours ago, Jeff Alson said:

Gore would require at least 3 of the top 5 Cubs prospects, and probably more. I don't think the Nats want to trade him, and I don't want to destroy our farm system to get him.

I used to think a starting pitcher was our top priority, but I have changed my mind, I think it is a right handed hitting 3B. Swanson has often batted 4th against lefties and 5th or 6th against righties, and while he has had a decent overall year, he is a weak hitter to be batting in those key spots for a playoff team, especially with his poor hitting with RISP. We need at least an average hitting righty 3B and then Counsell can choose between him, Swanson, Kelly, Amaya, and Hoerner for the key righty spots, depending on which players are hot.

In the playoffs, with all the off days, most teams only use 3 starting pitchers all the time, and occasionally a 4th starter. Boyd and Imanaga are obviously our top two, and Taillon, Rea, Horton, and Brown give Counsell a group to choose from depending on healty and effectiveness, or the depth to go with a bullpen game, which some teams have been doing in the playoffs. Going all in for "top 3" starting pitcher would destroy our farm system, and going for an "innings eater" starter wouldn't change our odds much in the playoffs.

With Steele out, we can't match the starting pitching of the Dodgers or Phillies or most of the other NL playoff teams, so instead I would rather focus on a deep offensive lineup, a great defense, and good base running. I believe a righty 3B and a good reliever with playoff experience would maximize our chances in the playoffs while maintaining most of our top prospects.

 

I think you should rethink this again. No question that starting pitching is the most pressing need. The second most is more starting pitching. After that maybe a 3rd baseman/bench bat or a pen arm. If you get two starters you might not need a pen arm. 

[Jeff Alson]

My point is that if Boyd and Horton aren't pitching in October, then the Cubs chances of making a deep playoff run this year are extremely low. even if we go all-in by destroying our farm system to trade for a couple of starters.

This is very different from 2016 where we were the best team all year and had one very distinct need. This year, even with many of our offensive players having career years, we are simply one of several top teams, will be underdogs in the playoffs to the Dodgers and almost certainly to the Phillies as well even if we go all-in, and this doesn't justify destroying the farm system and weakening our chances in future years.

[Bertz]

20 minutes ago, Jeff Alson said:

My point is that if Boyd and Horton aren't pitching in October, then the Cubs chances of making a deep playoff run this year are extremely low. even if we go all-in by destroying our farm system to trade for a couple of starters.

 

This is very different from 2016 where we were the best team all year and had one very distinct need. This year, even with many of our offensive players having career years, we are simply one of several top teams, will be underdogs in the playoffs to the Dodgers and almost certainly to the Phillies as well even if we go all-in, and this doesn't justify destroying the farm system and weakening our chances in future years.

The Dodgers won the World Series last year with Yoshi Yamamoto and a bunch of scraps.  The Rangers won the year before with Nate Eovaldi as their best SP.  The Braves in '21 had a formidable 1-2 of Fried/Morton, but neither guy was lights out in the playoffs (Ian Anderson was their best postseason pitcher lol).

Having the best SP is good obviously, but doesn't necessarily get you the title, if it did the Phillies would be looking to threepeat right now.  And then beyond that, if the Cubs add another good starter, their playoff rotation will match up with pretty much anyone except the Phillies and Tigers (or Dodgers if they get miraculously healthy).

[We Got The Whole 9]

I don't look at Morton as an innings-eating BORP. He's pitched 80 postseason innings and has a 3.6 ERA and FIP. He's been a 3.0/3.3 guy since 4/29. He's pretty much a must-get IMO. I don't necessarily agree that we need to add a controlled SP, TBH. I'd be totally happy getting Morton and Kelly and addressing the rotation in the winter.

 

Honestly I've come around to wanting Caissie around if they can't keep Tucker. It won't happen but i'd be fine renting.

 

Please don't bother with Alcantara this season, either. He's been way too awful to take a chance on this season. 

[Rcal10]

1 hour ago, Jeff Alson said:

My point is that if Boyd and Horton aren't pitching in October, then the Cubs chances of making a deep playoff run this year are extremely low. even if we go all-in by destroying our farm system to trade for a couple of starters.

This is very different from 2016 where we were the best team all year and had one very distinct need. This year, even with many of our offensive players having career years, we are simply one of several top teams, will be underdogs in the playoffs to the Dodgers and almost certainly to the Phillies as well even if we go all-in, and this doesn't justify destroying the farm system and weakening our chances in future years.

I don’t think they have to decimate the farm to get good rental pitchers like Kelly and Morton. I get not wanting Gore because of cost. But I do think deepening the rotation with solid starters is more important than getting Suarez. I would rather trade from our prospect pool for a rental starting pitcher than a rental bat. 

[Rcal10]

47 minutes ago, We Got The Whole 9 said:

I don't look at Morton as an innings-eating BORP. He's pitched 80 postseason innings and has a 3.6 ERA and FIP. He's been a 3.0/3.3 guy since 4/29. He's pretty much a must-get IMO. I don't necessarily agree that we need to add a controlled SP, TBH. I'd be totally happy getting Morton and Kelly and addressing the rotation in the winter.

 

Honestly I've come around to wanting Caissie around if they can't keep Tucker. It won't happen but i'd be fine renting.

 

Please don't bother with Alcantara this season, either. He's been way too awful to take a chance on this season. 

I would be good with those two and then maybe Castro for the infield and not lose any top 8 guys in the stystrm. 

[Jeff Alson]

One of the great things about baseball is that we get to "play" manager and GM.

I think it is a close call whether a #3/#4 starting pitcher like Kelly or Morton would help more than Suarez for the rest of the regular season, but I feel strongly that Suarez would be more important in the playoffs.  The Shaw-to-Suarez shift provides huge benefits to the lineup every day (and we would finally have a true right handed hitting cleanup hitter vs lefties) while Kelly/Morton would only provide a small benefit over Taillon/Horton/Rea.

With so few teams selling, the prices will likely be huge for Suarez and Kelly. I can't decide whether I would trade Caissie for a rental Suarez or not. I would not trade Caissie for Kelly.

[Rcal10]

44 minutes ago, Jeff Alson said:

One of the great things about baseball is that we get to "play" manager and GM.

I think it is a close call whether a #3/#4 starting pitcher like Kelly or Morton would help more than Suarez for the rest of the regular season, but I feel strongly that Suarez would be more important in the playoffs.  The Shaw-to-Suarez shift provides huge benefits to the lineup every day (and we would finally have a true right handed hitting cleanup hitter vs lefties) while Kelly/Morton would only provide a small benefit over Taillon/Horton/Rea.

With so few teams selling, the prices will likely be huge for Suarez and Kelly. I can't decide whether I would trade Caissie for a rental Suarez or not. I would not trade Caissie for Kelly.

No way in hell do I deal Cassie for Suarez. That is just awful use of your assets. 

[Tryptamine]

There is no recent world in which a rental hitter has cost a top 50 prospect, let alone a top 50, with helium and they're MLB ready.

[Bertz]

Realistically there's not a rental around this year that would cost Caissie, and it's not even close.  It would take a really extreme example for a hitter to cost that much, someone like Tucker coming available.  SPs cost a premium at the deadline so it wouldn't take as extreme of an example, but I still don't see it among current options.  Dylan Cease, Michael King, and Framber Valdez are the guys who might warrant it on talent, but their teams aren't selling.

When we traded for Jeimer Candelario at the deadline two years ago he was the best rental bat moved, and he cost the Cubs' 14th and 16th best prospects.  The equivalent today would probably be something like Will Sanders and Pedro Ramirez.  Christian Franklin and Ryan Gallagher would be another comparable package.

Caissie seems very likely to get moved, but it's almost surely going to be for someone under control through at least next year.