MLB Trade Deadline: Who might the White Sox and Cubs target in trades?

On Monday, Aug. 3, the MLB trade deadline will pass at 5 p.m.

Soon after that, the playoff pictures for the Chicago Cubs and Chicago White Sox will become clear.

Here's a look at who the White Sox and Cubs could target in trades as the MLB Trade Deadline approaches.

Cubs: Who can they afford?

Biggest Needs:

Starting pitching and relief pitching.

What we know:

The Cubs are in the same boat as they were last year at the trade deadline: in need of pitching. They need a starter and a reliever. Perhaps multiple relievers, too.

It stands to reason the Cubs would try for one of the biggest names on the market. Tigers’ ace Tarik Skubal and Padres closer Mason Miller would be those names. After that, Joe Ryan and Josh Hader are next on the wish list for most teams. 

Miller and Skubal are arguably the best pitching prospects allegedly on the market. "Allegedly" needs to be said because it’s not a forgone conclusion the Padres and Tigers will trade Miller or Skubal, respectively.

Skubal has won the last two AL Cy Young Awards, and Miller currenly has a 0.84 ERA, 26 saves and 79 strikeouts as San Diego's closer through Friday.

The Cubs also might not have the ammunition to land even one of those top pitchers, while keeping assets to acquire more help.

Instead, the next tier of pitchers – namely, Freddy Peralta, Case Mize, Anthony Weaver, José Soriano and Brooks Raley – might be more realistic. 

Last year, they added pitchers Michael Soroka, Andrew Kittredge and Taylor Rogers at the deadline. Kittredge made the biggest impact, pitching in key moments during the 2025 NL Wild Card and NLDS rounds. None of those three players remain on the current roster. The Cubs would most likely prefer to target pitchers with multiple years of team control.

Justin Steele is also set to return in the second half of the season. When that specifically is will remain to be seen, but that would add a starter to the rotation. 

The Cubs have had some free agency hits (Trent Thornton, 2.70 ERA; Jacob Webb, 2.91 ERA) and some free agency misses (Phil Maton, 6.18 ERA). But the hits make it easier to zero in on a reliever who will solidify a bullpen that has some talent in it already.

What we don't know:

It’s still unknown how aggressive Cubs President Jed Hoyer will be.

Players like Skubal and Miller will most likely be too expensive. That’s okay, that means there will be other more affordable players.

The top of the Cubs pipeline includes players like Josiah Hartshorn, Ethan Conrad, Pedro Ramirez, Jaxon Wiggins and Jefferson Rojas. They also have players who have spent considerable time in the big leagues, like Matt Shaw and Moises Ballesteros who might move the needle in deals.

There’s a fine line between selling the system and holding on to prospects for too long. The Cubs didn’t want to sell players like Ballesteros, Kevin Alcantara and Owen Caissie to protect the future.

But, in order to acquire that can help the team win a title, the Cubs need to be aggressive in some aspect.

That will come to light in a week.

What they're saying:

"Just make the team better," Cubs manager Craig Counsell told reporters on Tuesday.

"There's a bit of a spectrum of aggressiveness," Cubs second baseman Nico Hoerner said. "It isn't chosen by the players, but we dictate that by being the best version of ourselves. You want to put your team in the best place to believe in what we have and what we can improve on."

White Sox: To buy, or to stand pat?

Biggest Needs:

Pitching depth and a catcher.

What we know:

The White Sox have a surprise this year and have a better chance of making the playoffs this year than the last three seasons combined.

The core of prospects the White Sox have built over the last few seasons are the reason why. It’s why they’re one of the teams expected to be buyers at the trade deadline this season.

That’s also a reason why the White Sox need to make a move and deepen their staff.

Sean Burke and Davis Martin have pitched over 100 innings already this season, while Anthony Kay and Erick Fedde are also approaching 100 innings pitched. Adding a starter to the rotation would take some stress off their arms. But, the White Sox have options there.

The White Sox could get Drew Thorpe back before the end of the season. Hagen Smith might make the jump from the minors to the majors, too. Shane Smith is also an option to re-join the rotation.

Tanner McDougal can join the bullpen out of the minors. But, imagine what a White Sox playoff push would look with one of the following: Luke Weaver, A.J. Minter, Brooks Raley, Huascar Brazoban. 

Adding a catcher made its way to the priority list when Kyle Teel went on the injured list with an ankle sprain which could keep him out for multiple months. But, the necessity for that move depends on how the team views the Drew Romo and Edgar Quero combination internally. 

The White Sox would need to give up a player of value to get something in return, but the White Sox have prospects. It all depends on what White Sox general manager Chris Getz is comfortable giving up.

What we don't know:

What kind of player would the White Sox target?

Most likely someone that would fit their timeline, which would mean a player that’s under team control for two or more seasons.

The main goal would be someone like Miller, but the Padres would have an astronomical price tag and that's a move the White Sox would make down the line if they're a World Series contender.

Angels’ starter Reid Detmers would be a player that fits this bill. So does Luke Weaver, who is in the first year of a two-year deal. Reds' starter Brady Singer fits the mold, too.

That shouldn't completely limit the White Sox. Even an addition like Padres’ reliever Adrian Morejon, who would be a rental, would improve the bullpen and improvement would go a long way for a team that has playoff aspirations.

The White Sox are expected to be buyers. What that looks like will manifest itself soon as the deadline approaches. It’ll be a welcome change on the Southside after the team sold its best-performing big leaguers the last two seasons.

What they're saying:

"Naturally, you're going to think, ‘OK, how does this factor in the future here,’ whether it be at a future deadline or in the offseason?" Getz said after the first round of the 2026 MLB Draft on July 11. "But there's another angle to look at it, is that it gives you more prospect capital in the Minor Leagues to make future moves as well.

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