In fairness, you contradict yourself here. You say Lester was 100% worth every penny (any sane Cub fan would agree) and you say that Heyward was unfortunate since he regressed far more than any metrics would have anticipated and other teams were ready to offer him the same money (agreed) and Yu was a bomb. I'll roll with Yu as a bomb.....that basically makes Theo 1-2 with a push (Heyward) on those massive deals. Not sure I'd handcuff a GM over that.
The young pitching thing is a valid criticism. I would hope we'll see some of those young arms take jumps this year and be successful at AA & AAA. If not, there likely need to be substantial changes within the player development system.
All that said, maybe the budget situation is a blessing in disguise. If we look back at Theo's FA history, it's largely been good. Maybe having him chase a couple guys who aren't top tier would be a good thing. Here's a sample of the overall FA activity since Theo got to Chicago:
Great: These are guys who have been quality signings worth their money and/or played massive roles in the Cubs' resurgence
- Jon Lester: Duh
- Jason Hammel: He might not have been "great" as a pitcher, but he was a solid piece of the in-season rotation for the 2015 Cubs and was very good the previous season, which allowed him to be traded with Samardjiza for Addison Russell
- David Ross: Helped the Cubs grow up and ended his playing career with a WS game 7 home run off Andrew Miller.
- John Lackey: Another vet that gave the young Cubs an edge. Wasn't always great, but he pitched a lot of big games.
- Ben Zobrist: In spite of bad/injured 2017, he's been worth every penny of his contract and beyond.
- Dexter Fowler: As he went, the Cubs went in 2016.
Solid: Here I'll put guys who were useful as solid role players and/or as parts for positive returns via trade.
- Reed Johnson & Paul Maholm: Decent players included in trade for Arodys Vizcaino, who was ultimately dealt for TLS
- Luis Valbuena: Signed in 2012 and later included in trade to the Astros for Dexter Fowler
- Jorge Soler: Made contributions on 2015-2016 Cubs and was dealt for Wade Davis
- Scott Feldman: Key piece in the deal for Jake Arrieta
- Carlos Villanueva: Included in trade for Justin Wilson and Alex Avila
- Scott Hairston: Traded for Ivan Ineyro, who was traded for Dan Haren, who helped the 2015 Cubs get into the playoffs.
- Chris Coghlan: Important depth piece of 2015-2016 Cubs
- Emilio Bonifacio: Signed and included in deal for Victor Caratini
- James Russell: Productive bullpen arm in 2015 and included in deal for Caratini
- John Jay: Out-produced his contract in 1 year stint
Bad: These will be the signings that were big money for no performance - guys who didn't perform close to the level of contract they were given. I'm not going to include players who were signed cheap and didn't perform here.
- Edwin Jackson: 4/$52M was Theo's first big signing and he was dreadful.
- Jason Heyward: He'll never play close to his contract in spite of a glove & arm that are still elite. He came to Chicago and lost his bat along the way.
- Yu Darvish: Huge contract and delivered absolutely nothing in 2018.
- Tyler Chatwood: See Edwin Jackson deal. Same $/yr, awful performance.
- Brett Anderson: Bad deal on injury-prone pitcher