I don't remember Theo being irrational. The Phillies signed Bryce Harper, Cubs fans cried, and Theo signed zero-tool Daniel Descalso to a 2-year deal with a buyout for the 3rd year. This is what they do.
IMO if most Cubs fans were the GM they would panic after every big signing and Boras would fleece them every winter. Then they'd take their salary as GM and lose it all in the stock market lol.
Being a GM isn't much different than playing the stock market. Buying high, selling low, and making decisions based on emotion is a recipe for disaster. The Mets often buy high and they usually suck. The Braves didn't build their team in FA, they let Freeman and Swanson walk and used the money to extend all their good young players, and almost all their best players are still in their prime years.
Craig Counsell is a smart dude and if he's sold on Jed's vision then i'll give Jed runway.