Cubs Are Surefire Buyers Ahead of MLB Trade Deadline With Clear Needs

The Chicago Cubs have lived up to the heightened expectations that were placed on them coming into the 2025 MLB regular season.

With a 28-19 record, they are atop the National League Central, two games ahead of the St. Louis Cardinals and have an adventagoues schedule to cement playoff status.

To remain in that position, the Cubs know that they need to be aggressive ahead of the trade deadline, as it should come as no surprise that they were listed as one of the biggest buyers should the deadline have been today by Tim Kelly of Bleacher Report.

Motivation should be high on the part of the front office with Kyle Tucker set to hit free agency once the season is over. There is no guarantee that he will be returning to the club, especially with how well he has been playing.

Tucker is playing at MVP level, along with center fielder Pete Crow-Armstrong, as the foundation of the team’s incredible offensive production.

Chicago can score with anyone, possessing a lineup that is producing top to bottom.

What Do Cubs Need To Target Ahead of MLB Trade Deadline?

Where they need to find some help is on the pitcher’s mound, where injuries and effectiveness have hit the team hard.

“There's a lot of positivity surrounding the Cubs, and rightfully so. But they need to improve their pitching staff to have a chance to defeat the heavyweights from the NL West and East in the playoffs,” Kelly wrote.

Losing Justin Steele to a season-ending injury and Shota Imanaga being sidelined currently is putting a strain on the team’s depth. Matthew Boyd, who signed as a free agent, has been phenomenal, along with fellow offseason addition Colin Rea.

How many, if any, front line starters will be available for Chicago to pursue?

Sandy Alcantara has not looked the same in 2025 and no one is going to meet the asking price the Miami Marlins have set with his current form. 

It is hard to envision the Seattle Mariners or San Diego Padres unloading their pitchers as rumored over the winter, but the Cubs must scour the market for starting pitching help.

Similarly to 2024, the bullpen remains a sore spot.

Ryan Pressly, acquired after Tucker from the Houston Astros in a separate trade, has struggled at points and may not possess the requisite stuff to succeed as a closer.

The expected heir apparent, Porter Hodge, has also had some bumps in the road after a stellar debut in 2024.

Adding another reliever to the mix who has late-game experience should be near the top of the team’s to-do list. Kyle Finnegan of the Washington Nationals would be a good player to target.

Making a call to the Pittsburgh Pirates to check on the availability of David Bednar and Dennis Santana would be a smart move as well.

With a championship caliber offense, Chicago has to find the pitchers to help take their staff to that same level.