Has Keith Olbermann lost it? Maybe a little. By losing his job at MSNBC for donations made to Democratic Party candidates after appearances on his show (Countdown), he has taken a turn for the more opinionated, sometimes stepping over the line in terms of fact-reporting to get his political point across. At times, that has meant he sounds as nutty as Bill O'Reilly or Sean Hannitty (albeit with a totally different worldview and civil perspective), despite looking poised.
On the other hand, there were too few dissident voices in the news during George W. Bush's turn in the White House - with the consequences that we have seen (the largest foreign attack on U.S. soil, two wars, at least one of them fully unwarranted). The media had been way too lax and the entire planet suffered. I see how he would feel he needs to teach Americans the Right Way and, failing that, wanting to knock some sense into them.
All told, I think we're better off with him having some sort of wide and official platform.
Nowadays, Olbermann has a webseries called The Resistance (formerly The Closer, it was changed following Donald Trump's victory), hosted by GQ Magazine. Today's video brings home a point many scholars try to teach about but that people are too thick to open their eyes to regarding the Second Amendment of the U.S. Constitution: