When asked by Rick Warren what his most difficult (I think Warren used the phrase "gut wrenching") decision was Obama cited his opposition to the war in Iraq. This is not surprising because Obama clings to this decision, and the speech that went with it, with alarming desperation. He attempts to use it at every opportunity as proof that he has the judgment to be president; that his utter lack of experience shouldn't count against him. But the idea that this was a courageous choice is misleading.
As a number of people have pointed out, Obama at the time was a state senator for a liberal district. Being anti-war in Hyde Park isn't all that courageous. His liberal supporters were against it and his connection to the speech was a longtime supporter and fundraiser who was anti-war.
David Mendell's biography of Obama sets the scene:
As a still unannounced Senate candidate, Obama for months had been quietly courting what he considered his two strongest bases of support—Chicago’s so-called lakefront liberals and African Americans. The lead organizer of the downtown Chicago anti-war rally was Bettylu Saltzman, a liberal stalwart among the city’s elite lakefront crowd whose admiration for Obama dated back more than a decade.
Just who was Saltzman? She was an important person for an aspiring politician like Obama:
[H]er biggest political role came when, for four years, she ran the Chicago-based office of Senator Paul Simon. While working for Simon, Saltzman formed a close bond with one of Simon’s chief political minds—Axelrod, who had comanaged Simon’s first Senate campaign. The two would talk on the phone almost daily, each sharing a passion for political gossip and Chicago Bulls basketball. By 2002, Saltzman was a major Chicago fund-raiser who could not only tap into her own wealth but had big-money connections that could help raise substantial cash for any political candidate.
This is the political environment in which the invitation to speak was given and, later, accepted. As Mendell points out "Saltzman knew from conversations with the lawmaker that he did not support an Iraq invasion."
So this was not a decision that would test your conscience but rather a decision about what was the best political strategy. But even that wasn't that hard of a decision:
He consulted with Shomon, still his main political adviser at the time, and Shomon told him that it was a no-brainer—if Saltzman was urging him to speak, he could not refuse. Moreover, Obama was trying to draw Axelrod onto his Senate campaign team. It would not be wise to disappoint Saltzman if he wanted her to continue lobbying Axelrod on his behalf. So Obama agreed to speak.
So an important fundraiser and political figure in Obama's base, and a connection to key figures Obama is trying to attract, asks him to speak at a rally and say something he believes and this is a "gut wrenching" decision? This is his courageous judgment?
No, I am afraid this is just another indication that Obama is often a skilled politician who is not afraid to seize an opportunity when one is presented. Obama simply wouldn't have been able to run for the US Senate or for president without the backing of his rich liberal supporters and fundraisers. Making a speech against war was a smart thing to do and Obama was smart enough to recognize this and to take advantage of the opportunity (something Hillary Clinton was unable to do).
But it is far from courageous and it is an awfully odd example of a "gut wrenching" decision given the circumstances. Just another example of how Obama's words rarely match reality.