Cubs farm system faces a steep uphill battle the front office hasn't shown it can win

For much of my three-plus decades as a Chicago Cubs fan, the big knock on the organization has been that, for whatever reason, it can't develop top-end pitching.

There have been exceptions to the rule, sure. Kerry Wood, Mark Prior, Carlos Zambrano, Jeff Samardzija and, even though he was initially drafted by the Texas Rangers, Kyle Hendricks certainly deserves mention. Justin Steele, assuming he's back to 100 percent in 2026, can also be added to that list.

But when you consider the fact that Hendricks and Steele are really the only solidly above-average homegrown pitchers the team has developed in the last decade, it's a damning indictment on the front office - and Jed Hoyer, who was Theo Epstein's right-hand man for half of that time before taking over the big job himself.

That was a topic of discussion on the latest episode of the North Side Territory podcast, when Cubs beat writers Sahadev Sharma and Patrick Mooney chatted with Baseball America's Geoff Pontes about the publication's recently-updated Cubs' top 10 prospect rankings - which included just one pitcher in Jaxon Wiggins.

A top-heavy Cubs system sorely lacks high-upside pitching talent

Pontes said the Cubs' system isn't 'flush with talent' - and that once Owen Caissie and Moises Ballesteros graduate, without some new faces making some noise in 2026, the farm system isn't going to be widely viewed as an area of strength. Shortcomings both in the draft and with player development have led to the situation the big-league club finds itself in: being woefully shorthanded when it comes to elite pitchers.

“I get a lot of reports on like, what are these pitchers that they're drafting? People aren't thrilled with around the league. I'm saying they don't quite understand their tactics when it comes to drafting pitchers ... “I think they do a pretty good job in the early rounds. The models are supposed to eat in rounds 5-20, and they are just not doing that. I think some of it is what they are targeting.”

To address the elephant in the room, Cade Horton's breakout 2025 and runner-up finish in NL Rookie of the Year voting is one of the rare exceptions to the rule. But you can make the case he sort of bucked the trend of the type of arm the Cubs typically target. There were serious questions when Chicago took him with the seventh overall pick in 2022 - it was a high-upside roll of the dice and, at least to this point, it seems to have worked out.

But the Cubs aren't exactly known for taking those sorts of pitchers in the draft.

“They need to start targeting more upside and figuring out how internally they can then turn those upside traits into actual skills and production. For a team like this that's been lacking in pitching, I think it's something that's really, really hurt them.”

For years, Chicago has largely focused on college bats - and it's been a move that's paid off. Cam Smith, although no longer with the organization, spent less than a year in the minors, making the Houston Astros' Opening Day roster last spring after getting dealt in the Kyle Tucker trade. Matt Shaw, albeit with plenty of ups and downs offensively, was a Gold Glove finalist at third base as a rookie this season.

But if the Cubs refuse to swim in the deep end of the free agent pool, especially when it comes to pitching, and continue to fail to develop these badly-needed arms internally, this is going to continue to be a thorn in the team's side for years to come.