Theo has always been a players first guy.
I wouldn't be shocked if Hammel asked to be released thinking he can make more money in free agency and Theo granted it.
That being said, MLB Trade Rumors recently came out with a Cub-related article in which it discussed how bad (and its bad) the Cubs pitching situation is after next year.
I like the idea of Montgomery taking a starting role - he can pitch.
I also have a feeling the Cubs will take a run at a young starting pitcher and give up 2-3 top prospects for him.
I could also see the Cubs try and trade Soler and maybe one top prospect for Sunny Gray. A's were willing to trade him but demanded too much - ended up having a God awful year this year.