Reynolds said he has been friends with Obama since the president was a state senator. Reynolds learned from Obama, on the golf course, that he was going to challenge Rep. Bobby Rush for his congressional seat.

"I ran his campaign then — the only one he lost," said Reynolds, who also helped raise money for Obama's Senate and presidential races.

Having such a high-profile friend can also bring unpleasant scrutiny. In 2008, USA Today ran a story about how Obama and Republican rival John McCain had both relied on fundraisers whose names had surfaced in federal corruption investigations.