The Chicago Cubs have a clear lesson staring them in the face: if they want to build something that lasts, the farm system has to matter again.
MLB.com’s August farm system rankings told the story pretty bluntly. The Los Angeles Dodgers sat at No. 1, the Tampa Bay Rays were No. 2, and the Milwaukee Brewers checked in at No.
- Those aren’t rebuilding clubs waiting around for the future - they’re playoff teams.
That’s the point. A strong pipeline doesn’t just stock the cupboard; it keeps good teams good.
Chicago, meanwhile, landed at 28th overall, and that number reflects a lot more than bad luck. Players moved up to the majors.
Others were shipped out in trades to help the big-league roster right away. The result is a system so thin that the Cubs’ 2026 first-round pick, Cade Townsend, is already rated as the No. 4 prospect in the organization.
That is not where a club wants to be if the goal is another run at the World Series.
There’s a blueprint here, and the Cubs know it well. Theo Epstein built a winner in Boston by constructing the farm system first, then letting that talent carry the Red Sox to World Series championships in 2004 and 2007.
Even after he left, the benefits of that approach lingered for years. Epstein used the same philosophy in Chicago, rebuilding the Cubs’ talent base through drafting and trades until a young core and veteran additions finally brought a title.
But once that momentum was there, the organization never really protected it.
The Cubs started trading away minor-league depth to chase immediate help, and one of those moves made perfect sense at the time. In 2016, they sent top prospect Gleyber Torres to the New York Yankees for Aroldis Chapman, a deal that helped push them over the top. They were one piece away, and it paid off.
What followed, though, pulled them away from the kind of long-term base that keeps contenders alive. The 2014 MLB Draft is a reminder of what patience can look like: Kyle Schwarber, Justin Steele, and Dylan Cease all came out of that class.
Cease eventually got dealt, Schwarber left in free agency, and the Cubs were left wondering what might have been. A core built around those players, plus a healthy Justin Steele and an MVP in Pete Crow-Armstrong, is the kind of foundation that changes a franchise.
Jed Hoyer has tried to restore some of that balance. After the Cubs moved on from the earlier core, the farm system improved and looked like it was building toward something real behind Cade Horton and Crow-Armstrong. But that progress hasn’t translated into the kind of sustained breakthrough the organization wanted, and now the system has been thinned out again.
The list of talent sent away is a long one: Owen Cassie, Jackson Ferris, Moises Ballesteros, Jefferson Rojas, and more. On top of that, the Cubs have not gotten enough impact from the draft.
Dan Kantrovitz’s department has taken its share of hits, with Ed Howard missing, Jordan Wicks becoming a bust, and Matt Shaw looking more like a role or utility piece than a future star. That matters, especially with Alex Bregman brought in to replace Shaw at third base.
The Cubs also moved a 2024 first-round pick, Cam Smith, in a deal for Kyle Tucker, who was only a one-year rental. That kind of move has a cost, and Chicago has paid it in prospect capital.
The message is pretty simple: the Cubs need to stop treating the farm system like a trade chip bank and start treating it like the backbone of the organization again. They already have core pieces in the majors. If they want sustained success, they need development to be the priority, not the afterthought.
And if there’s one thing the current playoff field reinforces, it’s that the smartest teams keep feeding the pipeline. Chicago has to be careful with players like Ethan Conrad, Josiah Hartshorn, Myles Bailey, and Cade Townsend.
Those are the kinds of names that can become the next core. The Cubs need patience, smarter drafting, and a more disciplined approach to free agency if they want to get back where they want to go.
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