I think Bill Maher's expectation (as he expresses below) that Barack Obama would be more "Suge Knight" than "Wayne Brady" says more about Maher than Obama. Leaving the implicit racism of the joke aside, I don't think viewing Obama as a "wimp" actually gets you very far. I'm not enamored of his negotiation skills, but I don't think they come from any real fear of Republicans, as much as they come from his own political sensibilities. 

Maher believes Obama should see Democrats as "the party of the people." But that isn't actually who Obama is. His politics remind me of Lincoln Chafee's, and I think, were they not extinct as a political force, Obama could well be a liberal Republican. But most of those people are now Democrats. 

Lastly, I'm not convinced that Democrats are "the party of the people," or that such a party even exists. A certain share of this country is against repealing DADT. A certain share of this country could care less about torture, and have no problem with the War on Terror, or the War on Drugs.
"The people" are not noble or dastardly. "The people" is not a synonym for "all those who agree with me."