Chicago Cubs: A decade of falling short

Since the start of 2017, the Cubs have made the playoffs five times, won two playoff series, reached the 90-win mark three times, and had eight winning seasons. It averages out to roughly 85 wins a season (not counting the 2020 COVID year) over that span. Tell a Cubs fan that from 1950-2000, they are probably jumping for joy. It’s different when expectations change as drastically as they did after they won it all. These are not your father’s Cubs.

What stands out is how really only two teams (2017, 2025) arguably had a chance at a title. Even that is pushing it. It was more than clear the defending champs in ’17 were running on fumes at the end, and last year’s squad had maybe two trustworthy starting pitchers in the playoffs. Otherwise, two teams’ offenses “broke” at the end (2018, 2026), another two fell inches short of the postseason (2023, 2024), and others were either played a COVID “season” or were bad.

Cumulatively it’s been a step or two above “mid,” as the kids say. They’ve had fun times, great individual performances, notable players, and a few good seasons, but have fallen well short of ultimate glory. Not a laughing stock, nor a perennial bottom-feeder, but disappointing. For one reason or another, a fatal team flaw or two has doomed every season, preventing them from making a real run at a pennant.

Suppose one could say it could be worse. Many Cubs fans remember 80+ loss seasons being the norm. Plenty of other fanbases have had it worse than the Cubs in recent years. Still, the post-2016 era looked so promising, at least in terms of having more bites at the World Series apple. Onward we go.