Obama, at age 38, was a lecturer at the University of Chicago and a two-term state Senator. Though friends, including Terry Link, his colleague in the Illinois Senate, warned Obama against challenging Rush, as there was no obvious reason to displace him to the voters, Obama ran anyway, due to his frustration with what he claimed was Republican obstructionism in the Illinois Legislature and the feeling Rush wasn't representing the district as well as he could. Also challenging Rush were Donne Trotter, a state Senator, and George Roby, a police officer. Raymond Wardingly, a perennial candidate who worked as a clown, ran unopposed for the Republican nomination.
Obama entered the race in late September 1999, six months before the primary, stating Rush represented "a politics that is rooted in the past, a reactive politics that isn’t good at coming up with concrete solutions," while promising to build consensus and lead coalitions involving people outside of the black community to reduce crime, improve health care coverage, promote economic development and expand educational opportunities.
Early polling showed Rush's name recognition started off at 90 percent, with Obama's at 11 percent. Rush had 70 percent approval, while Obama had 8 percent approval. In the head to head matchup, forty-seven percent of the people polled favored Rush, 10 percent favored Obama, and 5 percent supported Trotter, who is also African American. Most of Obama's support came from Caucasians.
In mid-October, Rush’s son, Huey, was murdered, leading Obama to put his campaign on hold.GovernorGeorge Ryan called the Illinois Legislature to a special session to re-enact a package of gun-safety bills, a pet issue of Rush's, which had been overturned by the Illinois Supreme Court. Obama supported the package, but the session dragged on towards Christmas. Obama annually spends the Christmas vacation in Hawaii with his family visiting his grandmother, who raised him. Obama left Illinois, expecting the session would continue into January. However, a crucial vote took place earlier than expected, failing by five votes with Obama and others absent. Obama came under fire for missing the vote, though he said he would have flown back sooner, but his 18-month-old daughter was sick. Meanwhile, Rush received an outpouring of sympathy that aided his campaign.
As Obama lived in Hyde Park, a more affluent neighborhood with a higher percentage of White voters than the rest of the district, the narrative of the race became "the Black Panther against the professor" Obama frequently came off as uptight. Rush criticized Obama, saying "Barack Obama went to Harvard and became an educated fool. We’re not impressed with these folks with these Eastern elite degrees. Barack is a person who read about the civil-rights protests and thinks he knows all about it." Trotter said "Barack is viewed in part to be the white man in blackface in our community." Though the Chicago Tribune endorsed Obama, many, including local officials, PresidentBill Clinton, and Vice PresidentAl Gore, the Democratic Party nominee for President, endorsed Rush.
Obama raised enough money to remain competitive with Rush. However, he failed to connect with the working class African Americans of the district, nor did he provide a convincing reason for them to vote against Rush. Obama later wrote: "Less than halfway into the campaign, I knew in my bones that I was going to lose. Each morning from that point forward I awoke with a vague sense of dread, realizing that I would have to spend the day smiling and shaking hands and pretending that everything was going according to plan."
Obama later said he got "my rear end handed to me" in his loss to Rush, and acknowledged his own hubris. However, many analysts believe that Obama's loss helped him to learn from his mistakes, which enabled him to run more successful campaigns in 2004 and 2008. Obama was seen as a stiff policy wonk, and he used the experience to hone his ability to connect with voters. According to Chicago City Council member Toni Preckwinkle, an early Obama supporter, Obama "took a hard look at himself after that campaign and became a much better campaigner, more at ease on the campaign trail." He put more effort into his campaign, hiring David Axelrod as his chief political strategist. Also, Obama increased his focus on the Illinois Senate, improving his legislative accomplishments.