When the Chicago Cubs hired Craig Counsell, the goal was to win the World Series. Anything less than that was not good enough. That comes with handing Counsell the largest contract for a manager in baseball history.
After getting swept by the San Diego Padres in the Wild Card series, the Cubs have not come close to a World Series in three years under Counsell. Some of that is because of injury. Some of that is from underperformance. A large part of that is the inability to get the pitching staff right despite throwing a significant amount of resources at it.
It’s what Jed Hoyer, the Cubs’ president of baseball operations, was (rightfully) grilled on by Chicago media, especially David Kaplan, in his end-of-season press conference. To the question: "How big a failure is this team compared to previous years when you fell short?" He responded: “We let that opportunity slip away."
He also said, "The overall quality of our pitching needs to improve.” In reality, it’s been that same story for the past five seasons.
The Cubs need a rotation they can trust in October
The Cubs thought that the Edward Cabrera trade would drastically improve the rotation. Instead, he battled injuries, and finished with a 5.96 ERA in 18 games. Clay Holmes and Kevin Gausman were added at the deadline to bolster the rotation, and Holmes, who was rehabbing off a broken leg when acquired, finished with a 4.25 ERA in nine starts. Gausman, meanwhile, pitched through injuries late in the season and struggled, with his last start in the Wild Card round being a 3.1 inning clunker that allowed five hits and three runs.
The Cubs absolutely, 100 percent need to fix the rotation this winter. There are no half measures. They need to act on it and get it right. Because if they don’t, it’s likely going to cost Hoyer and Counsell their jobs.
A reunion with Holmes should not be ruled out. The Cubs coveted the right-hander at the trade deadline (spoiler: so did a lot of other teams). But Chicago specifically loved Holmes, especially because he’s a ground ball pitcher, envisioning that it would play hand-in-hand with the Cubs’ elite infield defense. While his numbers in Chicago were not what they envisioned, there’s a belief Holmes will be better in 2027 with an extended time removed from his injury.
But there will be competition for Holmes. There are teams out there who are already eyeing him in free agency.
Another target for the Cubs, meanwhile, should be Freddy Peralta. The right-hander has extensive history with Craig Counsell from their time in Milwaukee, and the two have a good relationship. He struggled mightily with the New York Mets after an offseason trade, leading to a midseason trade to the Tampa Bay Rays. But he bounced back in Tampa and has a 3.25 ERA in 10 starts, with early buzz that he could draw the start in Game 2 of the American League Divisional Series against the New York Yankees.
Other targets could include Sonny Gray, who has a mutual option in 2027 and is sure to become a free agent. Tarik Skubal figures to be too rich for the Cubs’ liking. Trevor Rogers has been up-and-down in recent years with the Baltimore Orioles, but is going to be one of the most in-demand pitchers. It’s hard to imagine that the Cubs will be fishing in the big aisle on the trade market, considering the assets spent to acquire arms in the last 12 months. So free agency should be where the Cubs do the bulk of their work.
Seiya Suzuki and Ian Happ could leave more holes to fill
The other crucial element of the winter will be on offense, where Seiya Suzuki and Ian Happ are scheduled to become free agents. The Athletic reported that the Cubs are unlikely to get into a bidding war for Suzuki, one of the top upcoming free agents, which likely means he’s headed elsewhere. Happ, of course, is a lifetime Chicago Cub. It’s difficult to imagine him leaving Chicago, and it would hardly be a surprise if the two sides stayed in touch all winter.
But the priority is, and will be, pitching. It’s been that story for five years. And Jed Hoyer’s job would seem to depend on getting it right.
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