The Chicago Cubs are doing unbelievably well at the moment.
They’re in first place, their offense has dazzled, their pitching has held, and there’s just a general good vibe all around them.
Good times don’t last, though, and the weight and strain of a long season eventually dulls good vibes, making teams pay for weaknesses not so evident early in the season.
And the Cubs do have their weaknesses.
Chicago Cubs Addressing Their Weaknesses

Third base is the obvious weak spot at the moment. There’s also a shaky, unpredictable bullpen. Starting pitching depth also has to be pointed at with the loss of Justin Steele and the lingering injury of Javier Assad.
In a perfect world, all of those questions would be answered internally, with a triumphant Matt Shaw return to the majors, Chris Flexen/Brad Keller/Cade Horton successfully rounding out the rotation, and the bullpen finding a consistent groove.
Unfortunately, baseball is rarely a perfect world.
The Cubs will have to make some deals at the trade deadline to pick up the talent needed to make a serious playoff run. But who could they realistically target and what would they be willing to give up?
Again, in a perfect world, Chicago would somehow convince their spiteful division rival St. Louis Cardinals to part with third baseman Nolan Arenado and/or closer Ryan Helsley, but that’s not likely to happen.
So, with not a lot on the market and a lot of competition to snatch up the few impact players available, the Cubs may have to do some workarounds when it comes to their third base and bullpen needs.
Options At Third Base And In The Bullpen

Could Eugenio Suarez from an out-of-contention Arizona Diamondbacks be a second-half solution at third? Maybe. Most likely, though, the Cubs will target yet another utility-type player to add to their third base depth pool while hoping and praying that top prospect Shaw makes himself major league-ready by July-ish.
There will be bullpen assets available at the deadline, but it’s most likely that Jed Hoyer and the front office will shy away from half-season rentals like Kenley Jansen in favor of more moderately-priced middle relievers and bullpen role players. 40-year-old former Cub David Robertson, who is still an unsigned free agent, is an interesting bullpen option if he can be scooped up soon enough and given some spring training-type innings before jumping into mid-season play.
The Cubs could be conservative when it comes to third base and bullpen acquisitions because they may be all-in with their pursuit of a starting pitcher.
“All-In” For Starting Pitching Impact Player

There’ve been lots of rotation names tossed about for Chicago, but the most persistent is the Miami Marlins’ former Cy Young winner Sandy Alcantara, who is coming back from Tommy John surgery, but is an attractive target due to having two full years of team control, plus an option for a third.
Per Tim Kelly of Bleacher Report:
“While the New York Yankees, San Diego Padres and New York Mets are among the other contenders who could stand to add a front-line pitcher, the Cubs are the most motivated to be aggressive.
They’ve lost Justin Steele for the year to elbow surgery. And as much as they surely hope to retain Kyle Tucker beyond 2025, they’re only guaranteed one season with the star outfielder because he’ll have plenty of suitors in free agency in the offseason.
President of baseball operations Jed Hoyer will have to give up more than he’s comfortable with to obtain Alcántara, but he would be getting a workhorse for up to three postseason runs.”
The Minnesota Twins’ Pablo Lopez and the Seattle Mariners’ Luis Castillo are also top starting pitching assets offering years of team control.
Other Cubs options include Tyler Anderson of the Los Angeles Angels and Joe Ryan, also of the Twins.
Expect the Cubs to be aggressive in their pursuit of a front-of-rotation starter at trade deadline, giving up some young talent, including, likely, at least one of their Top 5 prospects.
And, because of that, they will choose to be conservative elsewhere.
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