The 20th century left, broadly defined, has always had problems with democracy. If the left is supposed to speak for the majority of people, and the nation in which a particular left exists is more or less democratic, why can't they just win? The Marxist left devoted a whole lot of energy to this question -- theories about the interests of the proletariat being the only really important and historically necessary interests of society, theories about how the vanguard party spoke for the ignorant proletariat, and of course a wide range of theories about false consciousness. All of this can pretty easily be dismissed along with the rest of Marx-worship, now that it's over.
Then the left-liberals had their turn. "What's the Matter With Kansas" and all that. People are supposedly fooled by social issues into not understanding their real, economic interests as defined by people who know better -- this is leftist false consciousness writ small.
Occupy, as I've written before, commonly confused their slogan with their political reality. "We, are, the 99% -- and you are too!" makes a good chant. But of course it's politically false. 99% of the people at the bottom of the wealth distribution share the defined characteristic that they are the 99% of people at the bottom of the wealth distribution, but this does not make them vote the same way or believe the same things or have the same political interests. The Occupy people that I saw were in the main that part of the white left-leaning intelligentsia that did not currently have a 9-5 job.
Who is the conservative base in America? John Quiggin looked at that here. 49% of working-class white people vote GOP. And they make up about a quarter of the GOP base. The largest group in the GOP base is middle-to-high income white people without college degrees. The left in the U.S. is mostly non-white people and educated but not rich people. The left is not "the working class" and does not speak for the working class. Nor does the working class, as a reified entity, support the left.
The whole idea of democracy breaks down, or at least becomes highly hypocritical, if you don't think that people are the best judges of their own interests. I don't think that the left should come up with a new round of excuses for themselves and for that part of the working class that is "supposed" to vote left but doesn't. What are some of those interests?
A good number of the working-class people in America are racists, to take one common example. Racism is perfectly rational for some of those people, just as rational as support for oligarchy is for some rich people. They're never going to do well no matter who is in charge, and racism gives them the comfort of knowing that no matter how poor they are, they're white, and therefore according to their values always at least one step from the bottom. That is more important to them than any economic solidarity that the left would like to pretend exists. That is their overriding political interest: the defense of a value system that gives them a sense of intrinsic worth. They aren't being fooled by racism into letting elites manipulate them. It's a trade-off: they give the elites support for oligarchy, and the elites give them support for racism.
It's not all racism, of course. The match to Romney's moochers and looters speech is supposed to be Obama's clinging to guns and religion speech. People find self-worth in all kinds of things. I wouldn't say that what's politically important to them is fake and what's important to the left or to me is real. I would, of course, say that what they believe is destructive and wrong, and that I think they should be defeated. But there is no magical solidarity between us that occurs because we are all in the 99%.
I don't know what the answer to this is, in practice. But the left's categories and self-image seem to me to be all wrong, inherited from an era in which we lost, and in which the strongest parts of the left were authoritarian in any case. I've always understood the left to be about freedom: the negative freedoms of people not controlling your actions as long as you aren't hurting others, the positive ones about using socially created wealth to give everyone the resources that they need in order to act, the overall support for a functioning ecosystem that is required for people to do anything. Being on the left has nothing to do with who is or is not a worker, or who is or isn't wealthy. It has to do with what kind of society you want to live in.