The All-Star Break has come and gone and we’re about ready for the stretch run of the 2026 MLB season.
The trade deadline is just around the corner and the playoffs not far behind — though you wouldn’t know it with the insane heat (and smoke) weighing down Chicago this week.
With four days to catch our breath before the second half, we solicited some of our diehard fans for burning questions in our latest Cubs mailbag.
We answered some of these in our Wednesday show, but this column includes some in-depth answers as well as new questions that we didn’t hit on during the show.
Catch the full episode here:
Note: Some questions have been lightly edited for clarity.
How does Alex Bregman come out of the All-Star Break? – warriors.fan35
It’s a great question, Warriors Fan. In fact, it’s one of the biggest questions of the second half, I think.
Not just how Bregman fares in his first few games of the second half — but how he performs overall in the season’s final two-and-a-half months.
Bregman has certainly done some things well in his first year in Chicago, but simply put, the Cubs did not pay him $175 million to slug .359 or be a below-average offensive player (96 OPS+ in the first half).
He needs to perform better than that, but there’s good news there. History tells us things will turn around for him — and the two home runs he hit last weekend right before the break are certainly a confidence-booster.
In his career, Bregman has compiled his best months in August (.963 OPS), July (.831 OPS) and September/October (.818 OPS). He’s a second half player who heats up as the weather does and as the season moves along.
2023 is a perfect example of this.
With the Astros that year, Bregman had only a .387 slugging percentage and .726 OPS in the first half. After the break, he slugged .507 with a .901 OPS.
The Cubs are certainly hoping history repeats itself once again, because they could use another big-time bat in the lineup alongside Pete Crow-Armstrong.
Can the bullpen please not be so absolutely horrible? – jj_die_17
Not sure I understand this question, JJ. I don’t feel like the bullpen has been “absolutely horrible” at all.
They rank right in the middle of the pack overall with a 4.09 ERA (16th overall in MLB) this season.
That said, the Cubs bullpen has struggled a bit lately, with a 5.04 ERA (which ranks 22nd in MLB) since June 1. But more than 20% of the runs they’ve allowed in that span came during two blowout losses (18-3 to Giants on June 5 and 17-1 to Cardinals on July 3).
I think the Cubs bullpen has actually navigated all the injuries well this season. Jacob Webb has been a relief ace all season while Ryan Rolison (2.80 ERA), Trent Thornton (2.48 ERA) and Tyler Ferguson (4.32 ERA) have been pleasant surprises.
Phil Maton just returned from the IL right before the All-Star Break and Daniel Palencia might be back sometime in the next few weeks. Plus, the Cubs will almost assuredly be in the market for multiple relievers at the trade deadline over the next two-plus weeks.
What is one person you think the Cubs should realistically trade for and what would you give up? Also, what is one unrealistic player you would trade for (that might be on market) and what would you give up? For example, I would put Skubal under the second question. – gaross18
Now let’s get into the trade deadline content.
These are great questions from Gary.
Let’s tackle these one at a time.
As for realistic trade options, I think there are actually quite a few pitchers that fall into this category. ESPN’s Jeff Passan and Kiley McDaniel put together a great list of the top 100 players who could be available at the deadline.
Here’s an idea that I think is relatively realistic: A big trade with the New York Mets that nets the Cubs a couple of important pitchers. Right-handed starter Clay Holmes ranks 27th on the ESPN list and left-handed reliever A.J. Minter sits at 36th.
Holmes, 33, is nearing a return after suffering a broken bone in his leg on a comebacker in May. When he has pitched this year, he has been excellent with a 2.39 ERA and 1.10 WHIP.
He has a player option for 2027, so he may also be a longer-term fit for the Cubs rotation if he picks that up.
But since that’s not a guarantee and given his age and limited track record as a starter, the cost for Holmes may not be exorbitant.
Minter falls under a similar category as a former top high-leverage reliever with the Braves who has dealt with injuries over the last few years. The 32-year-old lefty has a 1.50 ERA over the last two seasons with the Mets, but has appeared in just 32 games.
He appears healthy now and has 36 saves and 122 holds over his career that would make Minter a perfect fit for the Cubs in the back end of the bullpen.
Admittedly, I don’t know what the cost would be for a package of these two pitchers in the same deal. But I think the Cubs could make it work.
As for players I would give up in a deal this season, I think it’s a good time for the Cubs to part ways with Kevin Alcántara. He is in his last option year and could probably use a change of scenery given he has never been given an extended runway in the Chicago outfield.
Alcántara doesn’t have the same juice as a prospect as he once had, but he’s still a tantalizing player and should hold some value on the market. I also think the Cubs could part with Pedro Ramírez given they have limited playing time available for the switch-hitter in the infield (this season and long-term).
Beyond that, I think anything could potentially be on the table for the Cubs.
It would be hard to see them parting ways with Jaxon Wiggins given the dearth of top pitching prospects in the farm system. And Matt Shaw still holds a lot of value long-term for this team (I think he is a starting corner outfielder next year). Moisés Ballesteros is also still very young (just 22) and 2025 draft pick Josiah Hartshorn has absolutely exploded onto the scene this year with a monster performance in the low minors.
That quartet would probably be hard for any team to pry away from the Cubs.
Some other names who fall under the “realistic” category: Relivers Yennier Cano, Kirby Yates and Bryan Abreu.
At the top end of the range would be starting pitchers Freddy Peralta and Joe Ryan as well as closer Aroldis Chapman. Those players are all varying degrees of “realistic”, as the cost for a starter like Ryan (who is under team control through next season) would likely be very high.
Chapman would be the top reliever on the market, but the Red Sox just won nine straight before the break and are only a half-game out of a playoff spot. They may not sell at all.
The Mets are one of the few teams that look like obvious sellers right now and Peralta is set to become a free agent at the end of the season. There is obvious history and rapport there with Peralta and Craig Counsell from their time together in Milwaukee.
As for unrealistic, I agree with Gary that Tarik Skubal falls under that category. The Tigers have been surging and may not even be sellers and the cost figures to be astronomical — a price I don’t see the Cubs paying.
Another unrealistic scenario is outfielder Byron Buxton. On paper, that seems like a dream fit — he could potentially move to right field and make Seiya Suzuki the full-time DH. That would maximize the lineup and give the Cubs another very good-to-elite level bat. But he’s signed through 2028 and even if the Twins trade him, I don’t see the Cubs giving up what it would take to acquire him. Hoyer and Co. are likely going to utilize their top assets to augment the pitching staff, which is a much, much greater need.
What roster holes need to be plugged at the trade deadline? – Ed Helinski
This one’s easy to answer: Pitching, pitching and more pitching.
I can’t remember the last time it was so clear-cut at the trade deadline for the Cubs front office. Sure, high-end pitching would be nice — especially on the starting staff.
But adding any healthy, quality arms to this team would be a boost given the extreme bout of injuries the Cubs have had to endure this season.
I think they could also benefit from a veteran utility-type player on the bench who could fill a variety of roles — like Willi Castro last season.
What is the answer to life, the universe and everything? – mfjake34
42. Next question.
Will they resign Seiya Suzuki? If not, who or how should they replace him? – Willam
It’s a fair question to wonder at this time in the year. Both Suzuki and Ian Happ are free agents at the end of the season and it is difficult to imagine either in another uniform.
Happ, in particular, has been a staple in Chicago for a decade now.
But the Cubs clearly have to focus resources on the pitching staff in the offseason and it seems unlikely they would re-sign both players, leaving at least one corner outfield spot open next season.
As important as Happ is to the team, I think Suzuki should be the target if the Cubs only re-sign one of them. He provides valuable right-handed power and his offensive ceiling is as high as anybody on the Cubs roster.
Suzuki has also proven he can excel against elite pitching, hitting a pair of home runs off Jacob Misiorowski over the last year and also performing well against Mason Miller and Hunter Greene at times.
I think either way, Matt Shaw takes a corner outfield spot next season and runs with it. If Suzuki does return, I could see the Cubs shifting him to left field and handing Shaw the keys to right field — where he has held his own in his first year in the outfield.
Can PCA continue his MVP season? – grrttjhnsn
Yes, absolutely.
I feel much more confident saying that now than at this point last year.
Crow-Armstrong has made some real strides with his plate discipline and has developed into a truly dangerous hitter — not just a free-swinger like last season.
He already has accrued more WAR than last season and there are still 66 games to go. If Shohei Ohtani experiences more injury issues in the second half, it’s not out of the question to think Crow-Armstrong can overtake him for the NL MVP.
Can they catch the Brewers? – chicagoderek7
Yes.
Will they?
Let’s lead into the final question…
Considering we are seeing the Cubs offense getting back on track and we should see a healthier pitching staff with Taillon/Cabrera/Steele all making their way back, what are your realistic expectations for the second half of the season? – cory.sechrest
I think the Cubs end up leapfrogging the Brewers in the standings and win the division.
You hit the right notes, Cory, and factor in the Cubs adding to the roster from outside the organization ahead of the trade deadline, too.
The Brewers look as vulnerable as ever right now as they navigate pitching injuries of their own.
The Cubs enter the second half five games behind the Brewers, but they made up 2.5 games just over last weekend alone. It can be done, especially when the two teams still have seven head-to-head matchups left.
