And Democrats will CONTINUE to lose all but the easiest-to-win presidential elections until they do a few things:
1) Stop caving into the middle and the right-wing. When you act like a "centrist" or a "moderate" and vote in favor of FISA and the like, it doesn't make you appealing to the middle. It makes you look spineless. The American people can tolerate a President they occasionally disagree with, but they CANNOT tolerate a President who seems like he'll capitulate. If he capitulated to the middle on FISA, what would he give to Ahmadinejad or Putin? I'm not saying be a raging Dennis Kucinich, Ralph Nader-style liberal, but be firm on your positions. Michael Moore said it best: don't act like a Republican, boasting about how much you go to church and how much you love to hunt and what a strong national defense you want to have. If the American people are given a choice between a Republican and a Republican-lite, they're gonna go with the whole wheat bread, if you know what I mean.
2) Stop thinking positive campaigning beats negative campaigning. Democrats have, in all but a few of the past ten presidential elections, been doing much better over the summer than they did in the actual election. This is because, on most issues, the American people agree with the Democrats over the Republicans. But Republicans are fantastic at distracting Americans from the issues. In 1988, Michael Dukakis was leading George Bush by 17% coming out of the Democratic convention because the American people agreed with him on the issues. Then, oh noez, teh tank bitchez! And Dukakis lost by about 8%. The Republicans pulled it off the issues, and Republicans generally win character elections, mostly because the American people see them as much more principled and decisive than Democrats (see #1). Democrats thought, in 2004, that ignoring the Swift Boaters would work. Did it? See: US presidential election, 2004.
3) Stop thinking the American people want to hear complex, academic ideas. Why was Bill Clinton the first Democrat to win two presidential elections since Franklin Roosevelt? Because he had a simple message: it's the economy, stupid. Easy to remember, funny, catchy, and it centered around what most Americans were worried about during that election: the economy. Most Democrats seem to think that if they run a nuanced, complex campaign, they'll seem more intelligent and they'll win. Take, for instance, the 2004 presidential debates. John Kerry beat George W. Bush decisively in the debates, but he failed to swing low-information voters because he simply said too much at once. He didn't have a steady narrative that he hit on in every response that drilled its way into the voters' heads the way Bush's "flip-flopper" mantra did. In terms of being too intellectual and academic, think about the 1988 debates. Someone asked Michael Dukakis (who I suppose is the ultimate symbol of Democratic presidential election failure at this point) what he would do if a man raped and murdered Kitty Dukakis, his wife. Instead of being a normal, protective man, saying he'd wanna tear the sonofabitch apart, he said, basically, "I'd want to put him on trial as a criminal but I wouldn't execute him because I don't support the death penalty." The American people thought, "gee, what a spineless pussy." And when was the last time we elected as President a spineless pussy?
So, yeah. Unless Barack Obama can get a simple, basic mantra that sticks, a'la "it's the economy, stupid" or "flip-flopper," he's going to lose the most winnable election for Democrats since 1932. (Of course, maybe the Democrats could've done themselves a favor and not nominated someone so unelectable and unwelcome in Middle America.)