First of all, he is well-spoken and reasonable. That, combined with the disillusionment (to put it mildly) of the electorate with the Bush administration, enabled him, and an unusual number of Democrats, to get elected in 2008. Also, this large Democratic majority enabled the passage of some really good legislation including the Children's Health Insurance Plan, many parts of the healthcare reform bill, and the consumer protection bill for investors.
But the outlook soon became much grimmer, and Obama is at least partly to blame.
Jon Stewart accused him of being "timid." I'm not sure whether this is the correct word; I think I would say "not sufficiently aggressive" to the point of seeming naive. Nowhere in his interview with Stewart would he come out and say that the Republicans have savaged him and his adminstration at every turn -- even as they said they would do. Early on they made it clear that they would do all they could to make his presidency fail. And they have done exactly that. This includes voting pretty much unanimously, in both houses, against not just his programs, but against many of his appointments requiring confimation. They have held up ambassadorships and judgeships, and have threatened to filibuster every piece of his legislation. Yet, Obama couldn't seem to say anything negative about them. He kept saying that the Democrats did this and did that, and that the "system" in Washington, which includes the filibuster, is not conducive to progress. But: he couldn't bring himself to attack the Republicans by name and call them out (as he did John Boehner a few weeks ago).
This is not the way FDR would have played it. In a speech he made in Portland Oregon in 1932, he said:
"To the people of this country I have but one answer on this subject. Judge me by the enemies I have made. Judge me by the selfish purposes of these utility leaders who have talked of radicalism while they were selling watered stock to the people and using our schools to deceive the coming generation".
Obama could have said this quite aptly to Jon Stewart and the nation. The financial crisis he inherited was not some natural phenomenon, but was the result of greed and deliberately lax federal regulation of investment banking. The same people who created the crisis mostly came away rich, and are using their wealth to bankroll Republicans and Tea Screamers. Not a word of this from Obama. Some of the biggest advocates for investment banking, in fact, found their way into the Obama adminstration.Here Stewart got in his one zinger. He began with a quote from Obama himself:
"[You said:] we can't expect different results with the same people. And I remember when you hired Larry Summers, I remember thinking, well that seems like the exact same person."
Obama replied that [we were able to ] "stabilize the system, stabilize the stock market, stabilize the economy," and "in fairness Larry Summers did a heckuva job."
With the audience already laughing as they recalled Bush's praise of his FEMA buddy "Brownie" (Michael Brown), Stewart advised: "You don't want to use that phrase, dude" !!!
(What a straight line from the President!)
BTW, speaking to Obama's timidity: A recent survey of the armed forces indicates that soldiers and their families are OK with serving side-by-side with gays. Yet the Obama administration was quick to appeal a federal court decision declaring DADT unconstitutional. Why? They claim they were worried that allowing openly gay soldiers would upset the very people that the poll indicates are OK with it. Even the troops are ahead of the government on this issue. Harry Truman didn't have a problem with anyone's sensibilities when he unilaterally integrated the armed forces by executive order in 1948. But, then, Truman, like FDR, was a real fighter.