“He was blinded by his ambition,” Mr. Rush said. “Obama has never suffered from a lack of believing that he can accomplish whatever it is he decides to try. Obama believes in Obama. And, frankly, that has its good side but it also has its negative side.”

One talent of Obama's emerged from that race: raising money:

He raised more than $500,000 — less than Mr. Rush but impressive for a newcomer — tapping connections at the University of Chicago, Harvard Law School, law firms where he had worked, and a network of successful, black, Chicago-based entrepreneurs who have played an important role in subsequent campaigns.

President Clinton ended up endorsing Bobby Rush:

Mr. Rush won the primary with 62 percent of the vote; Mr. Obama had less than 30 percent. Mr. Obama was favored by whites but lost among blacks, Mr. Lester said. Looking back, some say the magnitude of the loss reflected Mr. Obama’s failure to connect with black, working-class voters. Mr. Mikva said, “It indicated that he had not made his mark in the African-American community and didn’t particularly have a style that resonated there.”

Obama was luckier in his next race, for U.S. Senate. By then, he had changed his strategy from focusing on issues to focusing on "hope."

“There was a gradual progression of Barack Obama from thoughtful, earnest policy wonk/civil rights lawyer/constitutional law expert to Barack Obama the politician, the inspirer, the speaker.” Denny Jacobs, a friend of Mr. Obama and a former state senator, agreed. “He stumbled on the fact that instead of running on all the issues, quote unquote, that hope is the real key,” he said. “Not only the black community but less privileged people are looking for that hope. You don’t have to talk about health care, you have to talk about ‘the promise’ of health care. Hope is a pretty inclusive word. I think he is very good at selling that.”

Obama won big in his first Senate race:

Mr. Obama won the general election with the biggest margin ever in an Illinois Senate race.

....He vanquished a field of multimillionaires, some more experienced and better known, and benefited from fortuitous domestic scandals that sidelined two opponents and left him facing a Republican widely seen as unable to win.

The LA Times also examines Barack Obama's record in Obama: a fresh face or an old-school tactician? It begins:

Now, promoting himself as a fresh face on the national political stage, proclaiming his distance from lobbyists and the Washington culture of special interests, Sen. Barack Obama (D-Ill.) has to contend with his own history.