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Chicago Cubs in 'extremely strong position' for trade deadline pickups, per insider
MLB: San Diego Padres at Chicago Cubs MLB: San Diego Padres at Chicago Cubs Apr 4, 2025; Chicago, Illinois, USA; Jed Hoyer President of the Chicago Cubs prepares to throw balls to fans before a game against the San Diego Padres at Wrigley Field. Mandatory Credit: David Banks-Imagn Images

The Chicago Cubs have been looking sharp since returning from the All-Star break. They definitely give off the vibe of being ready for a strong second-half run, even if they can’t seem to shake the red-hot second place Milwaukee Brewers, who are still just one game behind them in the NL Central Division.

That’s not to say that the team doesn’t need improvement and isn’t aiming to fill roster holes before the July 31 trade deadline.

Stars aligning for “aggressive” Chicago Cubs at trade deadline


MLB: San Diego Padres at Chicago Cubs MLB: San Diego Padres at Chicago Cubs Apr 4, 2025; Chicago, Illinois, USA; Jed Hoyer President of the Chicago Cubs prepares to throw balls to fans before a game against the San Diego Padres at Wrigley Field. Mandatory Credit: David Banks-Imagn Images

As a matter of fact, the Cubs, per multiple sources, are aggressively pursuing trades to help fortify the roster in hopes of a deep playoff run.

“No one is untouchable,” Cubs president of baseball operations Jed Hoyer recently told Marquee Sports Network, in reference to possible deals involving top prospects.

Jeff Passan of ESPN believes that Hoyer and Chicago are heading into this trade deadline rush in a uniquely strong position.

Per Passan:

“The Chicago Cubs need a starting pitcher. And while other teams’ needs are more urgent — the Phillies’ bullpen, third base for the Yankees and plenty more — the Cubs are in an extremely strong position.

They have the best run differential in baseball and the third-easiest schedule for the remainder of the season. Home-field advantage is within reach. The Cubs need a starter for innings, sure, but more than that because their playoff rotation at the moment has a gaping hole. Shota Imanaga and Matthew Boyd have pitched their way into two spots, but Chicago needs a similar caliber starter who it simply doesn’t have at the moment.”

Blessed with a deep farm system and motored by a front office with a good amount of spendable cash and a drive to make the postseason for the first time since 2020, the Cubs find themselves in a fairly good spot when it comes to available talent perfectly lined up with their most obvious needs.

A favorable market


MLB: Chicago Cubs Press Conference 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

Although it’s shaping up to be a seller’s market and there won’t likely be a true ace-level starting pitcher up for grabs, it seems that there will be a good amount of next-level pitching available. A good number of the available arms will also come with years of team control.

A Cubs front office known for its creativity just may be ideally set up to “win” this trade deadline and possibly even do so without giving up too many prospects.

“There’s not a ton of obvious sellers,” Hoyer recently told The Athletic. “It could be a little bit of a strange market that way. So I do think that you try to think about things creatively as you think about different teams. Some deadlines, it’s very obvious: Here are the six to eight clear sellers, and they have a bunch of players that are available. This year it feels like it may be a little bit of a different year.”

Cubs’ needs and wants


MLB: Pittsburgh Pirates at Los Angeles Dodgers Pittsburgh Pirates pitcher Mitch Keller (23) pitches in the second inning against the Los Angeles Dodgers at Dodger Stadium. Mandatory Credit: Gary A. Vasquez-Imagn Images

Chicago’s bare bones shopping list consists of a top-half-of-rotation starter and a third base option, as well as an additional arm for the bullpen or back-of-rotation insurance.

There are several starting pitching options likely to be made available as well as some bullpen assets. Arizona Diamondbacks slugger and soon-to-be free agent Eugenio Suarez is the dream pickup at third base, but competition from hot corner-needy contenders like the Yankees, Mariners, Tigers, and Brewers may drive the asking price too high for a 3-month rental player. It’s much more likely that the Cubs would get a bench asset on the cheap, who is third base-capable.

This deadline shopping spree should not cost too much in trade capital. Would starter Mitch Keller from the Pirates, IF/OF Willi Castro from the Twins, and a solid veteran reliever be enough to push an already-solid Cubs team deep into the playoffs? Quite possibly. Especially if pitchers Jameson Taillon, Javier Assad, and Porter Hodge can rebound from injury.

Maybe best of all, the Cubs could even avoid trading their top prospect, outfielder Owen Caissie, just in case Kyle Tucker opts to move on to a mega-contract elsewhere.

Time will tell.

This article first appeared on ChiCitySports and was syndicated with permission.

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