Until Jed Hoyer and Tom Ricketts face hard truth, Cubs are destined to keep disappointing us all

A lifeless Chicago Cubs offense was their undoing in the NL Wild Card Series in San Diego last week, but the starting pitching also left much to be desired. That's the second straight postseason a short-handed, under-gunned rotation was exploited in the playoffs - which one would think might prompt some soul-searching by Jed Hoyer and Tom Ricketts.

I doubt that's going to happen, but it needs to. The Cubs have a golden opportunity at their hands this winter, with massive dollars coming off the books and major needs on the pitching staff. Will they continue to 'improve around the margins' and play it safe with starters whose best days are behind them or will they rewrite the narrative surrounding the team in free agency?

Unless Cubs get serious, they're doomed to repeat same mistakes in 2027

There are two paths forward, and some combination of the two offers the best chance for success both in the short and long-term.

1. Flex your financial muscle and spend at the top of the free agent market
2. Address a decades-long inability to consistently develop front-of-the-rotation pitching

I'm not asking them to go sign Tarik Skubal (although they could and should be part of that conversation when the former Cy Young winner hits free agency this winter). But you can't keep adding to the middle of the rotation and then wonder why you're outmatched come October.

You can point to Cade Horton's breakout 2025 season as cause for optimism, but he missed virtually all of the 2026 season after suffering a major elbow injury in his second start and his status for next year is very much up in the air. Justin Steele should be at 100 percent next spring, but by the time he pitches again, it will have been two full years since he pitched in a big-league game.

Maybe Jaxon Wiggins ends up being everything we all hope he will or 2026 first-round pick Cade Townsend blossoms in his first full professional season. But, for years, the organization has failed to create that pitching pipeline and, when paired with an unwillingness to trade for or sign a true, established ace, it's led to disappointment and disaster time and time again.

Learn the lesson. Accept the truth you know but may not want to hear. Because unless that happens, no matter how brilliant Pete Crow-Armstrong is over the course of his extension that starts in 2027, this team is ill-equipped to make a serious run at a World Series championship.

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