Currently tied with the Philadelphia Phillies for the first Wild Card spot, the Chicago Cubs could look to be aggressive at the August 3rd MLB trade deadline. Adding more talent to an already talented roster could allow the Cubs to make a run at the National League Central-leading Milwaukee Brewers. Here are several moves the Cubs could make that would put them into World Series contention.
The two-time reigning Cy Young winner, Tarik Skubal, appears to be the belle of the ball when it comes to this season’s trade deadline. With the Tigers looking like they will not be replicating last season’s success, they could look to trade their ace for a legendary haul. With their lowest starting pitcher ERA being 4.30, the Cubs would be one of the first teams on the phone with Detroit about bringing in the superstar.
Picking up right where he left off, Skubal currently has a 4-4 record with a 3.15 ERA across 11 games started. The Tigers ace boasts a 75-to-8 strikeout-to-walk ratio and has given up 9 homers across 65 innings. During his two Cy Young-winning seasons, Skubal totaled a 31-10 record with an average ERA of 2.30. He also led the league in strikeouts in 2024 with 228 and then increased his strikeout number to 241 in 2025.
As one of the top pitchers in baseball, trading for Skubal will not be cheap for any team. While him being a free agent after this season would normally lower the price for a player, trading for Skubal will still cost several top prospects. Should the Cubs trade for Skubal, a package centered around pitcher Ben Brown and top prospect shortstop Jefferson Rojas seems plausible. They would also most likely need to include a young pitching prospect like Kaleb Wing.
Trade Likelihood: Low
The All-Star closer has been the subject of countless trade deadline rumors over the past few weeks. With the Boston Red Sox last in the American League East and outside the Wild Card race, they could look to move Chapman to a competing team looking for a closer. The Cubs would be the perfect candidate to trade for Chapman, as they do not have a dedicated closer this season.
In his second season with the Red Sox, Chapman has saved 16 games out of 18 chances. The All-Star closer has posted a 2.19 earned run average in 24.2 innings pitched. Chapman has struck out 32 batters this season while only walking 12. Even though this is the 17th season he has pitched in, Chapman has shown no signs of slowing down as an elite closer.
Danny Palencia leads the Cubs with only three saves, with nine other players having at least one save. Chapman has a mutual option that would vest if he pitches 40 innings this season with a buyout. Should he decline his option, he would be a free agent after this season, which would factor into any team trying to trade for Chapman. Trading for Chapman would likely cost the Cubs a pair of top-12 prospects, such as outfielder Josiah Hartshorn and pitcher Kaleb Wing.
Trade Likelihood: Medium
A name Cubs fans should be familiar with, Luis Robert Jr., could be an under-the-radar trade candidate to boost their outfield. After being traded to the New York Mets during the 2025 season, Robert Jr. has struggled with injuries, but would profile as a high-potential bounce-back candidate for the remainder of the season. With the Mets in last place in the National League East by a wide margin, they could be inclined to trade the outfielder and start rebuilding.
Playing only 24 games this season, Robert Jr. is batting .224 in his first season for the Mets. As he has been injured this season, his home run and RBI numbers are especially low, as he has not been able to get into a hitting rhythm. While his offensive numbers have been disappointing, Robert Jr. does have a 17-to-13 strikeout-to-walk ratio.
Unlike Skubal and Chapman, a team trading for Robert Jr. will not be acquiring a rental player. While he is in the final year of his contract, there is a $20 million team option for the 2027 season. Thanks to that relatively cheap team option, trading for Robert Jr. will still cost a team a premium package. The Mets would likely seek a top prospect like pitcher Jaxon Wiggins and a mid-tier prospect for the former All-Star outfielder.
Trade Likelihood: Medium
A realistic trade target that could slot into the Cubs’ starting rotation, Merrill Kelly, is another struggling player who would be a bounce-back candidate. Currently sporting a 5-8 record with a 5.84 ERA, Kelly would be a low-risk, high-reward investment that would not cost nearly as much as trading for a player of Skubal’s caliber.
With the Cubs firmly in the playoff hunt, the team will likely be buyers at the trade deadline. Trading for a top starter should be a priority for their pitching rotation to go along with a dependable closer, which they are sorely lacking. Adding a bounce-back candidate in the outfield could help spell any slumps their starters could face.
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