Cardinals-Red Sox trade might spook Jed Hoyer into making previous Cubs' mistake

A blockbuster trade between the St. Louis Cardinals and the Boston Red Sox has sent shockwaves through MLB, and its ripple effects could easily reach the Chicago Cubs' front office.

The trade saw the Cardinals send veteran starter Sonny Gray to Boston in exchange for MLB-ready starter Richard Fitts and Red Sox no. 5 prospect Brandon Clarke, who is a starter for the team's Single-A affiliate. Even with the Cardinals kicking over a significant chunk of cash, the Red Sox are trading two quality arms for a guy whose days of being an ace are well behind him as he heads into his age-36 season.

With the Cubs looking to upgrade their rotation, this trade could see Jed Hoyer balk at the cost of trading for a quality starter, which is exactly what he did at the 2025 deadline. The Cubs need to target a guy much more valuable than Gray, who is in the twilight of his playing career.

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Joe Ryan of the Minnesota Twins or Edward Cabrera of the Miami Marlins are guys who fit the Cubs' needs, but the price of younger, more controllable, and frankly more talented arms like that figures to be significantly more than what the Red Sox gave up for Gray. And the Cubs don't have as many highly ranked pitchers as other teams do, with their top-30 prospect list seeing more position players at the top.

It's hard to imagine the team parting ways with Jaxon Wiggins (No. 3), who would figure to be a main ask in a potential deal for a starter. Wiggins could be poised for a big-league starter job in the near future, and I honestly wouldn't blame Hoyer for clutching onto him given that Jameson Taillon, Matthew Boyd, and Shota Imanaga will all be free agents after 2026. As the team's highest-ranked pitching prospect, he climbed to the Triple-A level after a breakout 2025 campaign, where he posted a 2.19 ERA and 97 strikeouts over 78 minor league innings.

Still, there is a serious need for a rotation upgrade after starting pitching injuries proved to be a major obstacle in the Cubs' postseason success. This is why the Cubs shouldn't be shy with their payroll flexibility this offseason, as they can leverage their dollars for a quality addition like Michael King or Dylan Cease without giving up valuable prospect capital.