There are a plethora of options at Jed Hoyer’s disposal over the next 10 days as the Cubs trade deadline plan comes into focus.
They could go all-in at the trade deadline and add several impact arms. Or they could shop in the bargain bin and refuse to mortgage the future for pitchers who could help the team win right now.
Or anywhere in between.
One thing is clear: The Cubs need to do something to address their pitching staff before the MLB trade deadline passes at 5 p.m. CT on Monday, Aug. 3.
It’s worth the reminder that a lot can change in the next week-and-a-half.
The Boston Red Sox rattled off 15 straight wins, going from clear sellers to definite buyers in the span of three weeks. So any hope Cubs fans had of Aroldis Chapman riding in to save the bullpen (like he did exactly a decade ago) is essentially out the window.
The Red Sox surge also means a pitcher like Sonny Gray is also probably off the table — and it holds as an example to every other front office around baseball that they’re just a winning streak away from contention. That’s especially true in an American League that is rife with parity.
Because of that sentiment, most trades still figure to happen in the day and hours leading up to the Aug. 3 deadline — and not a week before.
Why would the Detroit Tigers sell Tarik Skubal now when they have 10 games left until the deadline?
Speaking of Skubal, he represents one of the most notable names potentially available at the deadline in recent memory.
A Skubal trade would be on par with the Randy Johnson (1998), C.C. Sabathia (2008), Max Scherzer (2021) and Rick Sutcliffe (1984) deals of an elite pitcher in his prime being dealt at the deadline. A generation of Cubs fans are well aware of what kind of impact Sutcliffe had on that rotation in ’84, but Scherzer, Sabathia and Johnson all carried ERAs under 2.00 with their new teams as well.
Skubal would be the absolute top of the mountain for the Cubs at the deadline — arguably the best pitcher on the planet (certainly with more of a track record than Milwaukee’s Jacob Misiorowski) arriving to help a team that boasts an elite defense and a very strong lineup and is sorely in need of high-end pitching.
If this were a “dream” scenario for the Cubs at the deadline, it would include Hoyer and Co. finding a way to acquire Skubal for the rotation and Mason Miller for the bullpen.
But this exercise isn’t a “dream” scenario. It’s an idea of how it could play out in realistic fashion for the Cubs.
Because this isn’t a video game. These are real-life decisions that have impact on people’s futures and because of that, the cost is a genuine factor.
If the cost for Skubal reaches outrageous territory, would the Cubs really pay it? Should they pay it?
This team has been among the best in baseball for much of the season — but they also had a monthlong stretch where they were the worst team in the league. And that losing period has them still chasing the Brewers in the division by seven games in late-July.
If the Cubs were staring down a high likelihood of winning the NL Central and securing a first-round Bye, Hoyer and Co. might be more inclined to go all-in at the deadline. But in a best-of-three Wild-Card series, anything can happen and that scares front offices off from selling the farm and mortgaging the future.
Then again, it’s not impossible for the Cubs to catch the Brewers. And acquiring elite pitching would probably go a long way toward helping Craig Counsell’s squad make a run at the division.
If the Cubs can make up ground on the Brewers (who are 5-1 since the All-Star Break) over the next week-plus, that could play a big role in how aggressive Hoyer will be at the deadline.
With all this in mind, let’s examine a perfect path for the Cubs at the trade deadline.
A perfect realistic path.
Disclaimer: These are simply my thoughts on a perfect path for the Cubs based on need and players that should be available as of right now. I do not know what the price will ultimately be for these players and there will certainly be other available options that materialize over the next week-and-a-half.
Starting pitching
Best bet: One of Freddy Peralta, Kevin Gausman or Clay Holmes
Peralta and Gausman are free agents after this season and Holmes may be as well (he holds a $12 million player option for 2027).
Given the Cubs’ current place in the standings, it seems far more likely right now that they will be shopping at this end of the starting pitching pool.
It will take a haul to get Skubal and probably would mean parting with an MLB-ready player like Matt Shaw or Moisés Ballesteros. Other starters like Joe Ryan and Reid Detmers would also cost more given they are under team control beyond 2026. But they would also give the Cubs starting options in 2027 (and beyond in some cases), when there is a need in the rotation. It’s possibly Hoyer and Co. could end up taking a longer view approach to help the team for multiple years rather than going all-in on this season.
Peralta and Gausman would be my top two targets here.
Both have long track records of success — and not just middling success. They’ve been in the conversation as two of the top starters in the game in recent seasons.
Both veteran right-handers are also in the midst of slightly down seasons — though underlying metrics indicate they are still performing at a high level.
Peralta has an unsightly 5.01 ERA with the Mets, but he has a 3.85 expected ERA and posted a combined 3.30 ERA and 1.09 WHIP from 2021-25.
Gausman has a 4.51 ERA, which would be his highest in a season since a 5.72 mark in 2019. But he also has a 3.67 FIP (Fielding Independent Pitching) and should benefit greatly pitching in front of the Cubs’ elite defense.
Jul 21, 2026; Toronto, Ontario, CAN; Toronto Blue Jays starting pitcher Kevin Gausman (34) throws a pitch against the Tampa Bay Rays during the first inning at Rogers Centre. Mandatory Credit: Nick Turchiaro-Imagn ImagesPeralta and Gausman also miss a lot of bats, averaging more than a strikeout per inning.
If the Cubs acquired either guy, they would undoubtedly slot into the playoff rotation and quite possibly would be a Game 1 starter.
Holmes is in a tier below the other two, given that he has only been a starter for the last two seasons and is still working his way back after missing the last two months with a broken leg.
But the 33-year-old right-hander has a 2.39 ERA and 1.10 WHIP this season and generates a ton of groundballs, which should play well with the Cubs infield.
And the most important fact: All three should be dealt before Aug. 3. The Mets are way out of the race and even though the AL is a crapshoot, the Blue Jays are nine games under .500 and 6.5 games out of a playoff spot.
Bullpen
Best bets: 2-3 medium- to high-leverage arms, headlined by Adrián Morejón, Yennier Cano, Garret Whitlock, Luke Weaver, A.J. Minter, Brooks Raley, Anthony Bender or Bryan Abreu
Again, in a video game world, Mason Miller might make the most sense. Or even Josh Hader (who also has two years of control left after 2026).
But either player would come at a huge cost and it’s hard to see the Cubs paying that right now. Especially with a farm system that doesn’t rank among the best in baseball and has seen quite a few players graduate over the last year or so.
It’s not off the table — the Cubs absolutely should kick the tires on Miller given the immense upside he would bring to this team. But the more likely path is the Cubs targeting a tier or two below.
Of the group listed above, several pitchers (Morejón, Minter, Raley and Abreu) are set to become free agents at the end of the season while the others (Cano, Whitlock, Weaver, Bender) are under team control beyond 2026.
All eight have extensive experience in high-leverage situations and would immediately slot into the latter innings for Counsell in Chicago.
ESPN’s Jeff Passan and Kiley McDaniel listed Morejón as the 29th best player who may be traded at the deadline, and one of the top relievers.
It would likely be a relatively high cost for Hoyer’s front office to acquire any of these eight pitchers — let alone multiple — but the Cubs could certainly use them for the stretch run and in the playoffs.
Closer Daniel Palencia should be back in the coming weeks, but an elbow injury that will end up costing him close to two months is definitely worrisome. Phil Maton and Hunter Harvey were the Cubs’ big additions to the bullpen in the offseason but Harvey has been out for three months with a triceps injury and Maton just landed on the IL for a third time with a knee issue.
Jacob Webb has been a rock in the bullpen all season and there have been some solid success stories in Chicago (Ryan Rolison, Trent Thornton, Tyler Ferguson), but the Cubs will likely need to add multiple relievers ahead of the deadline.
If the Cubs opt to shop in the lighter end of the starting market, they could go harder in augmenting the bullpen. In the playoffs, a dominant bullpen can help alleviate rotation issues.
Since we’re talking about a “perfect” path for the Cubs at the deadline, I could see them adding a lefty like Morejón or Minter and taking a flier on Abreu (who is having a down season after several dominant years in a row).
At the very least, I think the Cubs need at least one reliever on par with the eight pitchers listed above and one or two other bullpen options.
Position Player Group
Best bet: A right-handed hitting role player like Lane Thomas
The Cubs bench right now is a rather odd collection of pieces. Kevin Alcántara hasn’t proven that he can hit at the big leagues yet and with Matt Shaw on the IL, Counsell has resorted to utilizing both catchers in the same lineup against left-handed starters often (with one catching and one at DH).
Shaw could make his return in the next couple of weeks and that will be a pretty big boost to the team. But the Cubs might still benefit from a veteran right-handed bat on the bench to complement the left-handed Michael Conforto.
Thomas would be a perfect fit — a 30-year-old veteran who is a free agent at the end of the season and on a team (Royals) that is firmly out of the playoff race.
His splits this year are relatively even, but over his career, Thomas has mashed against lefties (.289 AVG, .848 OPS).
The cost to acquire him shouldn’t be exorbitant and would immediately strengthen the Cubs’ depth in both the outfield and from the right side of the plate.
The Cubs could then play the matchups with Conforto, Thomas and Shaw in the DH spot while Alcántara and Justin Dean head back to the minors.
Final Haul
The perfect realistic Cubs trade deadline haul: Kevin Gausman, Bryan Abreu, A.J. Minter, Lane Thomas and possibly another reliever.
Admittedly, I don’t know what the cost would ultimately be for those four (or five) players or if the Cubs would be willing to pay it.
But that group would certainly enhance this current roster in a major way and is a lot more realistic (and cost far less) than the Cubs paying for Skubal, Miller or Ryan.
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