It’s an old sports adage that the final leap to true contention is the hardest to make. It’s one thing to improve, like the 2025 Chicago Cubs, from 83 wins to 92. The next season is the key. Making the final leap is the most difficult one.

For a (not so fun) example, let’s look back 40 years into the past. The 1984 Cubs were flying high; 96 wins, an MVP season from young superstar Ryne Sandberg, and young prospects coming up like Shawon Dunston seemed to portend success. The entire rotation was brought back for the following year, including Cy Young Award winner Rick Sutcliffe (currently an announcer for ESPN) and future Hall of Fame righties Dennis Eckersley and closer Lee Smith. Wrigley was rocking, and surely this was the start of something special.

Then, 1985 hit. While not an awful team, the ’85 squad could only muster 77 wins, good for a fourth-place finish. A 13-game losing streak and a separate seven-game skid was too much to overcome. During that big losing streak, the entire five man pitching rotation was on the disabled list. Starting guys like 37-year-old Larry Gura and someone named Derek Botelho, the Cubs just could not build on 1984. Crowds by September were back in the 6,000 range and the excitement had fled.

So, what can we learn from then? What did the 1985 Cubs do that the current front office can avoid?

For starters, the 1984 Cubs featured Lee Smith in the bullpen, who remained a stalwart throughout his career. Beyond him, 31-year-old Tim Stoddard, 29-year-old George Frazier, and 32-year-old Warren Brusstar had solid years as well in 1984. In the offseason, Brusstar and Frazier were retained, while Tim Stoddard was allowed to walk to San Diego, the team that eliminated Chicago in 1984. 

The 1985 bullpen could not replicate their success. Frazier’s ERA ballooned from 4.10 to 6.39 the following season. Brusstar’s decline was even more pronounced; he almost doubled ERA his from 3.11 to 6.05. Stoddard, who regressed back to a 4.65 ERA in San Diego, was replaced by Lary Sorenson, who checked in with a 4.26 ERA.

What does this mean for the current Cubs? Well, they can’t count on aging pitchers with track records of spotty success to replicate career seasons. Caleb Theilbar is 38 years old; he’s more likely to have a season like his 2024 (5.32 ERA) than continue a late career renaissance. Andrew Kittredge has a nine million dollar option that should arguably be picked up, but relying on him to be a late-inning fireman is probably a fool’s errand. The bullpen can’t be counted on to replicate these outlier performances. Jed Hoyer has long been great at putting together solid relief corps with minimal investment, but part of that formula has been excessive change year over year. I don’t see a reason to mess with that concept for 2026.

What else plagued those Cubs of 40 years ago? The rotation was beset by injury, and really, it was not easy to expect that. Sutcliffe had three consecutive 200-inning seasons before a hamstring tear the next season. Dennis Eckersley had ten seasons of over 150 before shoulder issues in 1985, and Steve Trout had no injury history to speak of until an ulnar nerve issue that season. Scott Sanderson was the only Cub with an injury riddled past, but he had a long career beyond that campaign.

Looking at this past team and comparing it to this year’s Cubs team is a difficult task. The 1985 Cubs were built around a solid staff who they thought would last through the season; the 2025 Cubs were built similarly. But Justin Steele broke, Shota Imanaga was hurt and never came back to full strength, and Jameson Taillon missed time. They were saved by Matthew Boyd and Cade Horton, both of whom carry their own injury history question marks.

The Cubs need to be careful and not enter their season with the aforementioned players as their only options in the five-man rotation. There are higher-than-comfortable probabilities that all five miss time to injury. Cade Horton, for example, just pitched more innings than he has in his career, and has two major injuries in his recent past. Matthew Boyd similarly had an innings spike and was less effective as the year went along. 

It’s not breaking news that the Cubs need to address their depth on the rotation. They will not have 30 starts from these five starters; they will need to supplement somewhere. The Cubs already are putting a ton of hope in Cade Horton’s basket; some risk mitigation and additions would be beneficial. Even if it doesn’t come in the form of an ace like Tarik Skubal or Hunter Greene, some more middle-of-the-rotation depth (á la Colin Rea) should be treated as a necessity, not a luxury.

As you can see, there are some parallels between what the current and 1985 Cubs would try to do in the pitching staff. The bullpen will be a greater challenge to rebuild in numbers; the rotation will be a task in how to upgrade in quality and risk mitigation. As always, the rotation can make or break a season. It’s up to Jed Hoyer to learn from the past and make the decisions that will make for a special future. While the names and eras change, the lessons are timeless.