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Chicago Cubs should be eyeing White Sox series for shopping ideas

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MLB: Cincinnati Reds at Chicago Cubs Jed Hoyer Tom Ricketts

The Chicago Cubs are teetering on the brink of disaster.

That’s not exactly the expected opening line of an article about a first place team not far removed from a gloriously one-sided victory and riding high on a wave of excitement.

It’s the truth, though.

The disaster in question refers to the Cubs’ starting rotation, which is holding up remarkably well, despite currently missing it’s top two arms and a solid back-of-rotation piece.

With Justin Steele out for the season after elbow surgery, Shota Imanaga out with a tricky hamstring injury, and Javier Assad gone until mid-season with his ongoing oblique issues, the team is missing 60% of its projected rotation.

Tough Days Ahead, A Trade Must Be Made

Chicago Cubs, Matthew Boyd
May 11, 2025; New York City, New York, USA; Chicago Cubs starting pitcher Matthew Boyd (16) delivers a pitch during the first inning against the New York Mets at Citi Field. Mandatory Credit: Vincent Carchietta-Imagn Images

While Matthew Boyd and Colin Rea have stepped up to assume the ace roles of Steele and Imanaga– for now– and the offense has helped to overcome uneven performances from the rest of the rotation, eventually the team will feel the strain of not having a full starting five.

The season is long and grueling and the Cubs will need to add at least one full-time, front-of-rotation arm for what they hope to be a playoff run. So, it’ll be necessary to make some sort of trade by the deadline to shore things up.

That’s why the Cubs should be looking at this current White Sox series, almost as if they were browsing a catalog for shopping ideas.

Shopping For Sox?

MLB: Minnesota Twins at Chicago White Sox Shane Smith
MLB: Minnesota Twins at Chicago White Sox Apr 1, 2025; Chicago, Illinois, USA; Chicago White Sox pitcher Shane Smith (64) delivers against the Minnesota Twins during the first inning at Guaranteed Rate Field. Mandatory Credit: Matt Marton-Imagn Images

The last place White Sox bring with them a bevy of talented young arms and a significantly less impressive crew of position players. As a matter of fact, at the moment, their entire starting rotation is made up of 20-something talent.

And not only are the White Sox stacked with young arms at the major league level, they are also packed with pitching prospects in the minors, with four of their top ten prospects listed as pitchers.

It might be wise for the Cubs front office to give the Sox front office a jingle and have some conversations about a swap of young assets.

The Cubs organization is top-heavy with talented position players, but not so much with high-end pitching prospects, other than Cade Horton, who’s currently struggling to get acclimated in the majors.

Jed Hoyer and the Cubs crew could target Shane Smith, Sean Burke, Jonathan Cannon, Davis Martin, or, to a much lesser degree, the more well-weathered free agent Bryse Wilson. Free agent acquisition Martin Perez had been mentioned previously as a potential Cubs trade target, but he’s currently dealing with elbow issues on the 60-day injured list.

The Chicago Cubs And Chicago Whites Sox: Ideal Trade Partners?

Chicago Cubs president of baseball operations Jed Hoyer speaks before introducing Craig Counsell
Chicago Cubs president of baseball operations Jed Hoyer speaks before introducing Craig Counsell as new Cubs manager during a press conference in Chicago. Mandatory Credit: Kamil Krzaczynski-Imagn Images

In the past, deals between the crosstown rivals were considered difficult to make because of their rivalry. That’s just not the case anymore. The two Chicago teams are in very different situations right now and in possession of a good quantity of trade capital to help push them where they need to be.

The Cubs need majors-ready pitching. They need someone who can step into the starting rotation right now and deliver solid results every fifth game.

Given their frugal, budget-conscious mindset, they’d also really, really enjoy getting someone on the cheap with several controllable years ahead of them. Throwing trade capital around for names such as Sandy Alcantara and Tyler Anderson may be showier and generate a greater splash, but that’s not generally the “Cubs way” of doing things.

The White Sox, meanwhile, are in full rebuild mode and are stockpiling talent for a complete franchise turnaround in the not-too-distant future. They are also overloaded with pitching, not only sporting a good crew of young arms in the majors, but also in the minors, where they currently have, per MLB.com, the top two left-handed pitching prospects in all of baseball, Noah Schultz and Hagen Smith.

Could the Cubs entice the Sox with prospects such as Moises Ballesteros, Owen Caissie, Kevin Alcantara, and/or James Triantos?

Honestly, it’s possible that the Sox feel themselves so deep in prospects that they wouldn’t really want anyone from the Cubs.

But it certainly would make a lot of sense for the Cubs to try and grab at a South Side arm or two.


Source: https://www.chicitysports.com/chicago-cubs-chicago-white-sox-trade?utm_source=rss&utm_medium=rss&utm_campaign=chicago-cubs-chicago-white-sox-trade


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