Cubs trade deadline pressure exposes familiar Jed Hoyer ultimatum once again

Pressure is mounting for Jed Hoyer once again ahead of the MLB trade deadline. Last summer, the Cubs spent most of the weeks before the deadline in first place in the National League Central while having a clear need for a starting pitcher. Once the deadline arrived, the Cubs were looking up to the Milwaukee Brewers and walked away with Michael Soroka as the big-ticket addition.

This year, the Cubs once again have a clear need for a starting pitcher. Though, their situation may be more dire this year than it was last. With how the Cubs have played over the last month, there's a rising argument that they are one of baseball's most disappointing teams this year.

Complicating matters for the Cubs is that the Brewers aren't the only team ahead of them in the division this year. The St. Louis Cardinals are currently in second place, and 2.5 games ahead of the Cubs.

Even with everything that has gone wrong for the Cubs this year, it's still hard seeing a path where they become a complete seller. They remain over .500, and tied for the final spot in the National League Wild Card race. As long as those two things remain true, chances are Hoyer and Co. will fall on the buy side.

Can Jed Hoyer afford another Cubs' trade misstep?

ESPN's Buster Olney runs through a list of executives facing the most pressure ahead of the deadline, and Hoyer falls in No. 4. Olney mentions the need the Cubs have for pitching, but specifically suggests they need a swing-and-miss starter. He's not wrong, it's a need the Cubs have had for the last several years, and he mentions some familiar names. Tarik Skubal, Freddy Peralta, Robbie Ray, Sandy Alcantara, and Joe Ryan all get name-dropped.

Of course, this really isn't new information. If the Cubs are adding talent for the 2026 season at the deadline, their primary focus is going to be on pitching.

Instead, there's a need to wonder what's really at stake for Hoyer ahead of the deadline. Last summer, he approached the tentpole event in the final year of his contract. He signed an extension just days before. That's why it's hard to believe that Hoyer will face any consequences of substance if his moves at the deadline fall flat like they did last year.

Just year after endorsing the path forward with Hoyer, it wouldn't be like Tom Ricketts to admit that was a mistake. So while Hoyer may be facing pressure at the deadline, it's likely not going to be tied to his job status.

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