The Chicago Cubs are the 4th most valuable team in MLB but can't be bothered to spend

How has a team that is this valuable, that has produced this much homegrown talent, allowed so much of it to walk away? 

I’m not sure that we can get to the bottom of that question, but something that we as fans have to do is hold this team accountable. 

Winning a World Series in 2016 was fun, but don’t forget that there had been 108 years' worth of suffering before that. I refuse to accept that one World Series victory in the midst of all of that rebuilding was worth it, and you should refuse it too.

This is a long quote pulled from an article at the Athletic by Patrick Mooney and Sahadev Sharma, but it’s important to see how deeply the willingness to trust the process runs:

"The Cubs don’t spend money at the same level as the New York Yankees or Los Angeles Dodgers. The Cubs haven’t done the kind of 11-year, $288.7 million contract extension the Kansas City Royals just closed with young star Bobby Witt Jr. The Cubs don’t believe in awarding the type of lifetime achievement contract the Houston Astros just handed Jose Altuve. The Cubs haven’t collected No. 1 picks by tanking as much as the Baltimore Orioles. The Cubs didn’t mortgage their farm system this winter for an ace pitcher such as Corbin Burnes."

Mooney and Sharma, the Athletic

The Cubs don’t spend money like their two closest market-size and Forbes valued competitors. Why?

The Cubs haven’t done long-term extensions with talented prospects. Why?

The Cubs don’t award lifetime achievement. Why?

The Cubs didn’t mortgage their farm system this winter for an ace pitcher. Why?