1. I'm not going to argue any further about Joe Lieberman.
2. Senators are, of course, not perfect maps of their constituents. There are a lot of factors that influence politics. Some are laudable, some are not. Some of the ones that are laudable in theory can be horrible in practice. If politics were simple, we'd have it figured out by now.
3. My frustration with the left comes from their inattentiveness to the role that the voting public plays in shaping the nation's governance. And that's in part by necessity. Progressives love to style themselves as the party of "the people," of "true democracy." Maybe not as much any more, but I cancelled my subscription to the Nation in the 90s because I became so sick of leftists talking about their niche ideas as somehow representative of the popular will. The classic leftist narrative is of a committed band of publicly-minded activists relentlessly fighting off oppression to achieve good results for the people . . . regardless of whether the people actually like those results. Well, if that's your self-narrative, then it becomes inconvenient when the voters reject your ideas. Hence it becomes all about the media, or the corporations buying both parties, and so on and so forth.
That's ultimately the problem with the idea of "neoliberalism." The alternative to Reagan was never, ever going to be socialism -- not "democratic socialism" or "Scandanavian social democracy" or anything else. It was never going to be progressivism. The items on the menu were Reaganomics and Clintonomics. Contentions that they were fundamentally the same are not historically accurate and they are rather insulting to many people who spent a lot of time fighting to defeat Reaganomics.
4. One thing that changed my thinking about politics was reading about the 1968 Dem convention. The cops were hostile af to the protesters, and I agree with the characterization of the events as a police riot. But why? The protesters were there ostensibly advancing the interests of the working classes. Police are working class. Why did the police hate the leftists with such a virulent passion? Why did the police feel the desire to crack open protesters' skulls. Maybe it was because the protesters didn't actually speak for them? I did a lot of reading after that, and what I found was the now-accepted narrative of working-class resentment toward the populists who were supposedly championing their interests. Some of that was sociological (i.e. class- and race-based), but it was also because the progressives were out of touch with what the working class population really wanted.
Of course, this phenomenon is not new. Marx called it "false consciousness." That's all well and good if your plan is to take over the world by force, but if you're trying to win a democratic election, "false consciousness" is not necessarily a helpful concept. In practice, it amounts to dumping on the values that people find to be important, and thus losing votes.