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James Reynolds, who has raised more than $200,000 for the Obama campaign, is chief executive of Loop Capital Markets, a Chicago investment banking firm that specializes in municipal finance.

He began raising money for Obama more than a decade ago, and opened his Hyde Park home for one of Obama's first fundraisers during the 2004 Senate race, according to Hermene Hartman, a mutual friend.

"Jim and Barack are very close friends and have been for a long time," said Leslie Bond, a Chicago money manager and Obama fundraiser.

In 2003, Loop Capital Markets was seeking municipal bond business in Philadelphia when Reynolds began dealing with lawyer Ronald White, a confidant of then-mayor John Street. The FBI was tapping White's phone.

Municipal finance contracts — fees to lawyers, bankers and accountants who help cities borrow money by floating bonds — are frequently awarded without competitive bidding.

In Philadelphia, many were handed out with political considerations in mind, the wiretaps revealed.

Loop was awarded two no-bid contracts worth nearly $300,000, according to a later indictment of Philadelphia City Treasurer Corey Kemp.

Reynolds agreed to pay $30,000 to a shell company controlled by White's paramour, Janice Knight, according to court records. "I'll keep you out of it," Reynolds told White in an April 2003 conversation recorded by the FBI.

Municipal bond brokers are required by the Municipal Securities Rulemaking Board to disclose consulting relationships. Philadelphia Assistant U.S. Attorney Robert Zausmer said during the trial that White didn't want to be publicly linked with Loop because he didn't want his lobbying scrutinized.

Kemp got 10 years in prison for fraud and conspiracy.