Rather than getting lost in analogies, let's look back at what he was focusing on. He pushed through Obama care, closed out Iraq (sorta), and had to deal with the gov't shutdown.
He CLEARLY dropped the ball when it comes to NSA, though I would say he's got a halfway decent excuse in that he was probably lied to by Alexander and co., and the surveillance thing wasn't at the time a squeaky wheel.
For the sake of argument we can give him the benefit of the doubt up to the point when Snowden's leaks came out, because no one, it seems, really knew wtf was going on (this in and of itself is pretty damning for the NSA IMO).
I can give him the benefit of the doubt up to this point because he's trying to manage a MASSIVE federal gov't with an extremely acrimonious senate and congress. It smells a bit, since he was against warrantless wiretapping as an election line-item, but lying to get elected is apparently somewhat minor on the scale of sins in politics.
So benefit of the doubt (stretched, but no unduly ocnsidering it's politics) up to that point.
What punches Obama's ticket is how he's reacted since. He's regurgitated bullshit talking points and flubbed at doing anything to rein in this obviously unconstitutional set of surveillance programs. There is no plausible wiggle room in that for any "I didn't know" or "I was misled by my minions" routine. Since the Snowden leaks he is patently complicit in the surveillance.
I always knew my daughters were up to no good. Here's the proof. Why won't the government DO something about it? I'd blindly vote for any asshole, no matter how transparent and obvious their moral bankruptcy and psychopathy, so long as they make me FEEL safer.