Obama gave a wide-ranging speech about the "war on terror" today. I'll send you to the always awesome Charles Pierce for some reaction to the speech. I don't expect this speech to have much, if any, effect on policy. Congress won't all the sudden be convinced to close Gitmo. What this speech seemed like to me was a way for Obama to try and frame his legacy.
As he acknowledged, the topics he discussed can be very difficult issues. The answers aren't clear cut in many cases, though less clear cut than Obama wants to admit. For instance, he suggests that he has to send drones to kill people because someone sitting around thinking about killing people is the same as (or similar enough to) someone actively killing people. I think that's kind of ridiculous, or at least ridiculous to conclude that you need to kill that person instead of arresting them.
Anyway, I'm not sure why he chose today to make this speech. But unless he has learned nothing the past 4 years, he wasn't doing it just to try to change policy. I think this was meant to justify his policies to history and form a narrative about his legacy, one that shows he was operating under some sort of conscience or moral integrity. I don't think he mentioned the issue of executive power and its relationship to congress in the speech. But that's an implicit thing present in most of the policies he discussed.
I doubt he cares very much about executive overreach, especially given the Republicans that have been part of congress since he's been in office. Obama seems to fit alongside just about every executive throughout history that have not given back power that has been given to them. He's even sought to gain more power, despite coming off as the candidate that didn't want it, often criticizing the Bush administration's overreach. What I want to know is, at what point does executive power become so overbearing that a president genuinely wants to give back power? When do we get another person like George Washington that is so concerned about the stability of the gov't that they make it a point to try not to abuse power?
I'm not knowledgable enough about every president to know about each's record on the subject of executive power. But my bare-bones knowledge of our history suggests that Washington and James Madison were about the one ones who made legitimate efforts to not overreach. Madison even had a good excuse with the War of 1812. The British literally invaded and burned down the White House. But being the writer and huge driving force behind the Constitution, Madison understood that it's dangerous to invest too much power in the executive and balked at doing so. Things have obviously changed a lot since the days of Washington and Madison. But it seems to me that someone with enough courage and long-term vision would find it useful to give some power back to congress and try to make sure the executive branch doesn't abuse power. I just hope things don't get too out of control before this sentiment becomes popular.