Obama was in a shitty situation from the very beginning.
I always felt that Obama came into office as a naïeve novice but at some point the politics of being the president hit him. With that I mean both parties that have bunch of people that are convinced that their idea's are right because of XYZ or because they get money from certain groups to believe that (probably the latter).
Gitmo is still open because of democratic obstruction and not just republicans, Obama signed the executive order but congress blocked him from closing the prison.
Obama has been really active lately doing whatever because the next president isn't a democrat but Trump. What does Obama care if Trump wants to fill the swamp currently he is president and he can do whatever he feels like it without thinking to much about the politics side of it.