“America is no longer what it could be, what it once was.”

I suppose, most charitably, what Baby Barry is referring to here is the glorious Clinton administration. Or, perhaps, LBJ’s conception of the "Great Society," the years, that is, before the welfare system was dismantled? 

Taking his various writings and statements as a whole, and his work as a community organizer into account, what I think he means is that the country no longer seeks to care for everyone to the extent that it once did. And he’d like to take us back to that time, higher taxes and all. But it’s possible he means something else. In the meantime, before he gets around to clarifying himself, he’s making some folks pretty angry.