Jed Hoyer clearly didn't learn anything from his biggest offseason mistake

Jed Hoyer wasn't alone in not meeting the sky-high asking prices on controllable front-end starting pitching at this week's trade deadline. None of the big names changed hands. Sandy Alcantara and Edward Cabrera stayed put in Miami, MacKenzie Gore is still in D.C. and, even after watching the roster around him absolutely decimated via fire sale, Joe Ryan is left standing in Minnesota.

But the Chicago Cubs were in a unique situation heading into Thursday. They had the second-best record in the league, but also put themselves in a 'win now' situation given what they gave up to pry Kyle Tucker away from the Astros last winter. A free agent at year's end, it will take ownership and the front office going to unprecedented lengths to keep him in Chicago past this season.

So if you want to make the most of it, you have to get uncomfortable. The same expression that Andrew Friedman applies to free agency can be used here: "If you're always rational about every free agent, you will finish third on every free agent." Guess what? If you're always rational about every trade target, you will miss out on every trade target.

Cubs' Jed Hoyer clearly isn't a guy who likes being uncomfortable

I'm not saying the Cubs should have stripped its farm system bare for a rental. That would be foolish, at best. But there were several top-tier arms with multiple years of control available via trade and Hoyer flat-out refused to step up and meet the steep asking price (again, as did the rest of the league).

“It was a tight starting pitching market — very few rental starters,” Hoyer told Marquee Sports Network. “Obviously, a lot of time, energy and focus was on controllable starters — the guys that everybody’s been talking about. Ultimately, none of those guys moved. We didn’t match their price, but no one else did either ... “It would have been so detrimental to our future that we decided against it."

What makes this even more painful, though, is this is the same lesson the universe tried to teach this front office and ownership group this spring, when they made a late push to sign free agent Alex Bregman, only to low ball the offer and see him sign with Boston. What happened? They've spent the entire season trying to stabilize the third base position - with little to no success until very recently.

I'm not condoning approaching every trade deadline and offseason with an AJ Preller-like reckless abandon. But, at some point, the Cubs are going to have to push well outside their comfort zone and take a big swing. Because it's those moves that can ultimately change the trajectory of a team.