Later that year, Yehudah associates pitched in an additional $5,000 to help retire Obama's debt. The contributions were recorded on Oct. 7, 2000, three days after the Illinois Senate, at Obama's behest, approved a $75,000 state grant to Yehudah's nonprofit, state records show.
In an interview, Yehudah said the commitment for the grant was secured months earlier, in July. He called timing of the donations a coincidence.
The donations were modest by political standards, as was Obama's relatively small assist to the nonprofit group of his ex-rival and new benefactor. But in Illinois, "government actions often occur around the time of campaign donations," said Stewart of the Better Government Assn. "The answer is always the same: It's always a coincidence."
Obama spokesman Bill Burton said there was no connection between the campaign donations and the grant to Yehudah's organization. "Of course not," he said.
By 2002, Obama was preparing for his next challenge, a run for the U.S. Senate. Also that year, the Illinois attorney general sued Yehudah over allegations of kickbacks unrelated to the state grant. It was settled out of court.
Three days after the suit was filed, Obama returned one batch of donations totaling $5,000.
Political alliances
In November 2002, Democrats took control of the Illinois Senate. Emil Jones Jr., 71, a 34-year veteran of Springfield and the new Senate leader, said he was approached immediately by Obama.
He "knew if he had me, it would give him power," Jones said in a recent interview. "Having me would force politicians in Chicago to be supportive. I could leverage folks to raise money."
Obama told Jones: "You have the power to make a U.S. senator."
"That sounds damned good. Let's go for it," Jones said he replied.
With Jones' help, Obama got his pick of bills to champion leading up to the 2004 election.
In a state where numerous death row inmates were wrongly convicted, Obama took the lead on legislation requiring that police videotape murder confessions. After a Northwestern University football player died, Obama pushed a ban on the sale of an herbal stimulant, ephedra, thought to be implicated in the death.
For Jones, it was more than a political alliance. He said he came to regard Obama "like I feel about my own son."
From his early days in state politics, Obama also opened relationships with moneyed interests that have continued into his presidential campaign, contributing to his record-breaking fundraising statistics.