I think that, at least in part, this meme is how parties excuse their inability to deliver once they secure power. In Obama's case specifically, I don't know how a guy who had been a community organizer since the 80s, who'd been a senator since the late 90s was so caught off guard by the legislature once he had executive power at his disposal.

But yet they both did actually do a bunch of other things, especially exercising the power of the bully pulpit.

Or alternatively if we do take it for granted that presidents are quite constrained in what they themself can do (aka "separation of powers"), then why is the original comment talking as if there would be some massive sea change next time when there wasn't one last time?

This seems like another bit of Schrödinger's Trump. Like how he's both the most powerful most successful person, and also just an unfortunate victim that other people are always doing mean things to.