Some of you will only tip your cap to greatness if wine is literally made from water.
What Theo did in Boston was remarkable. If it was easy to build a team when you have the luxury of an open checkbook, every World Series would be a huge salary vs a huge salary. Certainly, he benefitted from having the money at his disposal, but they made some incredible under the radar moves, which was the difference between his WS teams and previous Red Sox squads.
Simply building the Cubs into the perennial playoff team is equally, if not more impressive. The Cubs were not just bad, when he came on board, they were annually trending worse.
Then you take into consideration the financial restrictions of the new ownership, and the fact it has been done with SOOOO much youth - opening the club's window of opportunity as wide as one could imagine possible.
If the Cubs break the curse, Theo would be in the conversation of greatest GM's in baseball history.
They acquired Arrieta, Wood, and Hendricks in incredible low risk trades and let them mature, almost on the backburner, as the initial attention was given to the stockpiling of young bats.
Then, only when they felt like they had the right keystone pieces in place, they went out and landed Maddon to do what he does so well and make the pieces work so well together.
For those unfamiliar with the situation the Cubs were in when he was hired, I recommend reading the following article (written prior to the 2014 season):
http://grantland.com/features/chicago-cubs-boston-red-sox-theo-epstein/(worth mentioning, it also makes mention that a large number of scouts had Jonathan Gray pegged as the #2 talent in the draft, ahead of Bryant)