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Chicago Cubs possibly played for suckers in trade deadline pursuits?
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 are heading into the final three weeks or so before the July 31 MLB trade deadline with a definite need– starting pitching.

The team would LIKE to have another quality arm to further solidify their over-performing bullpen, preferably one with closer capabilities as insurance for current closer Daniel Palencia. They’d also LIKE to have a quality bench asset who can play third base as well as outfield.

However, they NEED starting pitching.

Ace Justin Steele was lost for the season in early April, laid out by an elbow injury that required surgery. He’ll be out of commission until at least mid-2026. Projected fifth starter Javier Assad has been on the shelf all season so far with an oblique issue suffered in spring training. Shota Imanaga missed about five weeks with a hamstring strain. Now, Jameson Taillon is out with a right calf strain that could see him miss more than a month.

Chicago Cubs at a trade disadvantage


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

Heading into the dog days of summer and into the thick of a pennant race, the Cubs will need more than first-time All-Star Matthew Boyd, who’s been the true ace of the staff this year, and Imanaga, followed by rookie Cade Horton and veteran swing man Colin Rea for what they hope to be a deep postseason push.

And the rest of the league also knows this.

In what is already shaping up to be a seller’s market, Cubs president of baseball operations Jed Hoyer will be at a distinct disadvantage in trade talks precisely because everyone knows just how much the Cubs need starting pitching.

The Pirates may be playing the Cubs


MLB: St. Louis Cardinals at Pittsburgh Pirates MLB: St. Louis Cardinals at Pittsburgh Pirates

One team that seems to be playing the market in an attempt to artificially inflate the return on any trade they make is the Pittsburgh Pirates. According to a recent story from the Pittsburgh Post-Gazette, Pirates GM Ben Cherington has been strategically leaking info to the press that would work to his team’s benefit.

Per the Post-Gazette (subscription required):

“As recently as Friday, sources have indicated that Cherington has been allowing other teams to approach him with the first offer. One source also believes that most of the rumors connecting current Pirates players to potential teams of interest were leaked by the Pirates in an attempt to draw up further interest for assets that are indeed on the trading block.”

The idea of stirring up a bidding war among trade suitors is not a new idea, nor is it illegal or even, really, unethical. But it does show that rival front offices will be looking to get any possible advantage in pursuit of a greater return in trades.

The Cubs, who are reportedly one of the teams inquiring about starter Mitch Keller, are among the teams possibly being played by Cherington.

The increased asking prices


MLB: Chicago Cubs at Arizona Diamondbacks Mar 29, 2025; Phoenix, Arizona, USA; Chicago Cubs second base Matt Shaw (6) celebrates after hitting a two run home run against the Arizona Diamondbacks in the seventh inning at Chase Field. Mandatory Credit: Rick Scuteri-Imagn Images

According to that Post-Gazette piece, the Cubs have also expressed interest in Pirates third baseman Ke’Bryan Hayes, an interesting side note which could mean any number of things– primarily, a possible decision to move on from rookie third baseman Matt Shaw or a plan to flat-out trade Shaw at the deadline.

Every selling team will be looking to inflate their asking price for a top-tier starting pitcher at this year’s deadline. But they will especially look to take advantage in their dealings with the Cubs.

Will Hoyer have to give up more than he anticipated in order to get what he needs before July 31? Will he need to touch an “untouchable” in pursuit of starting pitching? Will his disadvantage in negotiations mean that he might even have to deal on-the-cusp guys like Shaw and Ben Brown?

This upcoming push to the trade deadline will be an interesting one.

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

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