For Obama, a Handsome Payoff in Political Gambles

In Obama's first successful campaign, he was not the candidate.

It was 1992 and he had recently finished Harvard Law School and returned to Chicago, spurning prestigious law jobs to work closer to the ground. He went to work for Project Vote, a voter registration drive that boosted the candidacy of Carol Moseley Braun (D), only the second black U.S. senator since Reconstruction. Sandy Newman, who recruited Obama, said he offered him the job with limited expectations. Fundraising was not in the job description, yet Obama "raised more money than any of our state directors had ever done. He did a great job of enlisting a broad spectrum of organizations and people, including many who did not get along well with one another."

Obama recruited a fundraising committee chaired by John Schmidt, a white former chief of staff to Mayor Richard M. Daley (D) and John W. Rogers Jr., a young black money manager and founder of Ariel Capital Management. In less than a year, Obama hired 10 workers, attracted 700 volunteers and produced 150,000 new voters.

By the end, Schmidt was struck by the fact that the drive actually registered voters.

"He really did it, and he let other people take all the credit. The people standing up at the press conferences were Jesse Jackson and Bobby Rush and I don't know who else. Barack was off to the side and only the people who were close to it knew he had done all the work."

Three years later, Obama ran for office himself. He used his elbows.

At the time, he was teaching constitutional law at the University of Chicago and working at a small civil rights firm after finishing his memoir "Dreams From My Father: A Story of Race and Inheritance." He spotted an opportunity when Alice Palmer, a progressive black state senator, ran for Congress in an off-year election.

Palmer assured Obama that she was comfortable surrendering her safe seat in a community that had produced a string of successful anti-machine candidates, including the late Sen. Paul Douglas (D) and Abner Mikva, future member of Congress, federal judge and White House counsel. She informally blessed his candidacy and said if she lost the House race, she would not drop back into the Illinois contest.

But after Jesse Jackson Jr. (D) won the special election in November 1995, Palmer had second thoughts. Her followers pressed Obama to drop out. He refused. Palmer and her supporters hurriedly gathered hundreds of signatures to put her name on the ballot.

Obama challenged the validity of some of the signatures on the petitions before the Chicago Board of Election Commissioners. He also contested the petitions submitted by his three other Democratic opponents. The authorities ruled all four opponents ineligible, clearing the field.

"It took some real guts to do it," Schmidt said. "There were a lot of people who said, 'You can't do that.' "

Toni Preckwinkle (D), a 4th Ward alderman, believes Obama did the right thing, although his maneuver left some hard feelings.