Ranking Chicago Cubs' Priorities at 2026 MLB Trade Deadline

The official second half of the season is underway, and the Chicago Cubs have come out ready to play. They took two of three at home from the surprisingly competitive Minnesota Twins. After their panic-inducing June, the team has played more like the one we saw early this season, firmly cementing their status as buyers. With the trade deadline less than two weeks away, let's rank the areas they can improve upon, starting with the least necessary and working up to the trades they need to make if they want to make noise in October.

5. Backup Outfielder
The Cubs have a need for better bench depth, with Matt Shaw on the injured list for a second time this year. Top prospect Pedro Ramirez and resurgent veteran Michael Conforto have performed well off the bench, and the return of Shaw will further deepen this group. If the Cubs want to pick up a luxury piece on the cheap, they can go after a backup outfielder who can slot in above Kevin Alcántara and/or Justin Dean. Both have difference-making speed, but a hitter with a more consistent track record of success could go a long way. We don't want to see another situation like the Terrance Gore 13th-inning at-bat in the 2018 play-in game.

It should be pretty easy to get Lane Thomas from the Royals, or Tyrone Taylor from the Mets. They could even reunite with Willi Castro, who can move all over the diamond. 

4. Platoon Partner for Ian Happ
For the most part, the Cubs lineup we have seen all season will be what we see the rest of the way and in the postseason. They have established regulars at every position, and they can all rake when they’re hot. As previously mentioned, a backup outfielder makes sense as their lineup is set, but if they want to take a bigger offensive swing, here is where they can. Ian Happ has struggled against lefties all season. Although he isn’t striking out from the right side at an alarming rate, he's hitting .160, with an OPS of .551. Benching a veteran leader on the verge of free agency is always complicated, even if it's only in roughly one-fourth of games, but it might necessary.

Orioles outfielder Taylor Ward is a rental and would make a ton of sense here. The Cubs could also call up their division rival the Reds and see what they would want for Spencer Steer, who can play a few positions and comes with team control. 

3. Left-Handed Reliever
It should come to no surprise that the final three spots on this list will be about the pitching staff. There's really no wrong way they can address the pitching staff. We've already seen them bring back old friends Drew Pomeranz and Aaron Civale, as well as trading for David Peterson, but it's not going to stop there—and not just because Pomeranz is already gone again.

As they continue to add pitching everywhere, they should target a high leverage lefty. Caleb Thielbar has not been nearly as effective as he was last season, but is still pitching higher-leverage innings, and who knows when Riley Martin will return? Hoby Milner and Ryan Rolison have been serviceable, but they each carry xERAs over a run higher than their actual ERA. A playoff series can go off the rails fast if they have to rely on these guys to get big outs. Please don’t tell me the plan A is for Justin Steele to come back and be a lockdown reliever.

About two and a half weeks ago, the easy answer here would have been Aroldis Chapman, but the Red Sox have flipped their season around as they are currently on a 14-game winning streak. (Besides, as Cubs fans know all too well, there's never actually anything 'easy' about acquiring Chapman.) All-Star Foster Griffin could fill a rotation spot now but slide into the bullpen come October. If the Astros sell, they should have no issue finding suitors for Steven Okert, and the Mets should look to sell both Brooks Raley and A.J. Minter. 

2. Closer
The highlight of Daniel Palencia’s 2026 is looking more and more like it was closing out the WBC for Team Venezuela, because the plan for him to close for the Cubs has not worked. He is also back on the injured list. Actually, the Cubs having a closer at all has not come to fruition yet. The team has a total of 20 saves, with Jacob Webb leading the charge with five. This is not going to work in the playoffs. They need a guy who has recent experience closing games. The good thing for the Cubs is that many of the elite teams do have the ninth inning covered already, so there might not be 10 teams making a mad dash for a closer not named Mason Miller.

The Cubs can certainly go for Miller, but he is arguably the hottest trade chip in baseball as the Padres fall further into seller territory. If they go for Miller, it could very well make it difficult for them to accomplish what you will read about next. Depending on how much further they fall out of it, could the Blue Jays look to move the cost-effective and controllable Louis Varland for a haul? The other options inspire less confidence, but still more than anyone the Cubs currently employ. This tier could include Luke Weaver of the Mets. 

1. Front-End Starter
This was the answer here from the end of April onward. The story of the Cubs’ season has been the injuries to their starting rotation, and how they have been able to overcome them to remain in playoff position. Edward Cabrera has a chance to return, but Cabrera has been a bag of mixed results all season, and Taillon just got back, but probably should be the last guy to look at for playoff innings with an xERA of 5.49.

With Horton going down after two starts, Justin Steele’s multiple setbacks, and emerging ace Ben Brown’s season in jeopardy, Shota Imanaga and his 1.4 fWAR lead the Cubs’ starters. Matthew Boyd has been okay, but the only thing he has proven is that the durability of his 2025 was an outlier. Outside of them, the most promising option currently active looks to be Javier Assad and his fWAR of 0.0, or David Peterson, who has looked good, terrible, and fine in his three starts as a Cub. Really, if they had the resources, they should go after two front-line guys, but with the state of the entire pitching staff, they need to allocate resources to acquire good relievers, too. (They also don't have the prospects to acquire more than one high-priority target this summer.)

Depending on how the next two weeks go for the Tigers, Tarik Skubal is an obvious choice here, but between his time on the shelf this season and the sentimental value he is worth in Detroit, the juice might not be worth the prospect squeeze for the Cubs. The Angels have recently hinted that they will listen on controllable starters Reid Detmers and José Soriano, and despite hanging on the fringes of the playoff picture, the Twins could be better off moving Joe Ryan. The Padres might want to move Michael King, but he has a complicated contract situation with which to deal. The best fit might be Freddy Peralta, who is a true rental and (barring injury) a lock to be moved—but he's also been bad and just got roughed up by a Brewers team the Cubs know they need to be able to beat. Another true rental is Kevin Gausman, who would be a good secondary piece next to a true number one. Failing that, he'd be a fine cog in whatever elaborate out machine Craig Counsell tries to build this fall.

The Cubs can't do all of this, or even close to it. They need to accomplish at least two trades that check boxes from this list, though. If they do, they still have a chance to make the kind of impressive October run fans have craved for a long time, but not tasted since 2017.