For those who have openly doubted Theo's ability (and I am guilty too) to build a contender without the tricks like over slot and trading for pending free agents for comp picks, here is a reason to believe in his regime's ability to find a way.
Besides the seemingly large strides the Cubs have made in the farm system, there is a gleaming ray of light. Theo and Jed have made some questionable investments (looking at you Jackson), they have made some incredibly intelligent moves that will help set up the future of this franchise.
I am referring to Castro in part (bargain contract), but Anthony Rizzo was maybe the best bargain in baseball. Theo saw what you see today in a prospect that few thought we would see. If you're knowing your head, good but you would be behooved to compare him to Freddie Freeman to get the full effect.
Freeman .275 BA / 11 HR / 35 RBI / .366 OBP
Signed at 8 yr/$135M ($16.87M AAV)
Rizzo .278 BA / 13 HR / 36 RBI / .403 OBP
Signed at 7 yr/$41M ($5.85M AAV)
Both play above average to plus defense. Theo got the same player at 1/3 the cost! That is $77M in savings that can be used to pay for another big piece. I am not proposing that Theo will get away with this on every extension but even the Theo haters should be singing his praise on this one.