Obama's Years in Chicago Politics Shaped His Presidential Candidacy

In 2000, Obama's ambition led him to run for Congress from Chicago in an ill-fated primary challenge to Democratic Rep. Bobby Rush, 53-year-old former head of the Illinois Black Panther party. The party's slogan was "Power to the People," and one of its projects was arming black men to defend their communities from the white-controlled police. Obama, 38, could never compete with Rush's compelling biography or charisma, and he couldn't overcome doubts that he was authentically connected to the black community.

To make matters worse for Obama, when Rush's son, Huey Rich, was shot to death on a South Side street in October 1999, public sympathy for him grew exponentially. That Christmas, Obama and his family visited his grandmother in Honolulu, and he didn't return to Springfield to vote on a hotly contested gun control bill that lost by three votes, for which he was pilloried in the media. He also did poorly in a key televised debate. State Sen. Donne Trotter, an Obama adversary from Chicago, told the Chicago Reader newspaper in March 2000: "Barack is viewed in part to be the white man in blackface in our community. You just have to look at his supporters. Who pushed him to get where he is so fast? It's these individuals in Hyde Park, who don't always have the best interests of the community in mind." Obama lost to Rush by 30 percentage points.

But he would recover. "You saw his resilience after he lost to Bobby Rush," says Valerie Jarrett, a former senior city official who is now a close Obama adviser. "He has the intestinal fortitude to take a punch—and losing to Congressman Rush was a very hard punch."

But he continued to work actively in the community and look for another way up the ladder. He saw his chance in 2004 when a Republican-held seat in the U.S. Senate opened up. He took a risk and won, putting his Chicago education to good use and promoting the themes of conciliation, multiculturalism, and compromise.

Three years later, he was running for president.