Cubs can't ignore an important lesson from their Dylan Cease miss last offseason

Amid the Chicago Cubs' pitching woes last season, it was hard not to look up north to the ace pitcher they could've had in the offseason. Dylan Cease was the big name many had circled in free agency as an obvious target for the rotation in the offseason. For a team that had a lot of question marks with their staff, between Shota Imanaga's struggles in 2025, Matthew Boyd's health track record, Cade Horton's relative inexperience, and more, it made all the sense in the world to add a potential ace. Instead, he went off to Toronto for seven years and $210 million with deferrals.

That seemed like a lot at the time for a pitcher with an ERA north of 4.50 in two of the last three seasons. The Cubs, meanwhile, opted to take a gamble that they could unlock Edward Cabrera's full potential coming off his best season in the majors so far. Needless to say, that didn't pan out on either front. Cabrera only pitched 80 innings due to injuries, with comfortably the lowest strikeout rate of his career and a 5.96 ERA, while Cease is expected to finish as the Cy Young runner-up to Cam Schlittler, posting a 2.40 ERA and 2.56 FIP with a career-best 34.9% strikeout rate in 169 innings.

Obviously, nobody could've known that Cease was about to twirl his best season at age 30. However, there's an undeniable element of "you get what you pay for." Since the Jon Lester and Yu Darvish signings, the Cubs have been reluctant to extend for the longer-term, higher-dollar contracts it takes to lock down a top pitcher in free agency nowadays, even when the fit is obvious. While it's true that inking any arm in their 30s to five-plus years is risky, the real lesson is that it's even riskier to keep eschewing these deals entirely.

The biggest benefit of signing Cease for the Cubs, in addition to his talent, would've been having a starter known for his durability. All that the former White Sox and Padres pitcher has done since becoming a full-time big-leaguer is post. He's started at least 32 games for five straight seasons before dropping to just 29 last year. It's becoming a rarity these days to find an arm of that caliber who can so consistently throw quality innings.

By comparison, the Cubs have only had two pitchers reach 32 games in two or more seasons since 2016 — Jon Lester and Kyle Hendricks. Their workhorse starter this year was Imanaga, who bounced back well enough with a 3.77 ERA and 4.47 FIP, but was still plagued by home run troubles. The lack of a starter like Cease or Lester is felt especially when there are so many other players with an injury history missing significant time.

Cubs need to start paying up for upside and reliability

Trading for Cabrera wasn't a bad decision in a vacuum, and taking risks when you think you can improve upon a player is something all good organizations do. However, with their own lack of pitching development, the Cubs have perhaps leaned too heavily on risk to get upside from their starters at a lower cost, when they remain the team with the second-lowest average fastball velocity in the rotation. It wasn't just Boyd and Cabrera who had spotty track records, but also Horton, who had his first Tommy John surgery in 2021 and only threw 34 1/3 innings in the minors

Their rotation is even more full of what-ifs than ever heading into 2027, with Justin Steele returning after essentially two lost seasons, Cabrera looking for redemption, and Ben Brown wrestling with a concerning neck injury. More than ever, they have to be willing to pay up for someone who can reliably take the ball every five days with confidence. This is a team that should be competing now, and the only way to get the rotation up to speed fast enough is to shell out.

Tarik Skubal has been what they need, nearing 200 innings in 2024 and 2025, and recovering quickly from elbow surgery to remove loose bodies earlier this year. The Cubs aren't likely to reach his asking price — even though they should be — so that leaves someone like Freddy Peralta, who has some stuff concerns after this year, but has bounced back in Tampa Bay and is on a four-year streak of 30+ games started per season with a 3.63 ERA and 3.98 FIP. It doesn't matter who it is in the end; they just can't afford another year of balking at reliability.

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