Cubs Have Clear-Cut Strategy To Execute Ahead of MLB Trade Deadline

The Chicago Cubs front office has clear goals to achieve ahead of the MLB trade deadline.

Nov 13, 2023; Chicago, Illinois, USA; Craig Counsell (L) smiles as he is introduced by Jed Hoyer (R), Cubs President of baseball operations as a new Cubs manager during a press conference in Chicago. | Kamil Krzaczynski-Imagn Images

The Chicago Cubs have been playing some excellent baseball throughout the 2025 MLB regular season, but there is still plenty of work to do.

Entering play on July 21, they have been unable to shake the Milwaukee Brewers, as the teams are tied atop the National League Central with identical 59-40 records.

That will create some fascinating headlines and stories to keep track of heading into the MLB trade deadline.

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The teams may be tied in the standings, but their goals ahead of July 31 likely don’t mirror each other.

The Brewers could do some buying and selling, looking to extend their window of being playoff contenders in what has been a pleasantly surprising 2025 campaign.

The Cubs, on the other hand, should be all-in as buyers with clear needs to address on the mound.

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There is pressure on the Chicago front office to upgrade the pitching staff in some capacity, making the most of what could be their only season with right fielder Kyle Tucker combining with center fielder Pete Crow-Armstrong as the most dynamic duo in the NL.

With their ace Justin Steele out for the season and veteran Jameson Taillon currently sidelined as well, there is a clear need for starting pitching help.

“Landing an impact arm is the goal, but the Cubs could also benefit from added depth as well. Next on the to-do list could be targeting some bullpen help or seeing if there might be an avenue for upgrading the production at third base,” wrote Jordan Bastian of MLB.com.

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How close to the top of the market Chicago goes will be dictated by how much ownership is willing to pay.

Inexplicably, after acquiring Tucker this past winter, the payroll was slashed compared to what it cost in 2024.

It was something that frustrated not only the agents of players seeking deals in free agency, but assuredly the fan base as well.

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Was it done with an eye toward adding talent in-season with trades?

Only time will tell if that was the case, but the Cubs cannot pass up this golden opportunity to contend for a World Series.

Their lineup can compete with anyone in baseball, so their focus over the next 10 days needs to be on acquiring as much pitching help as possible to stabilize the rotation and bullpen.

For more Cubs news, head over to Cubs On SI.