Jim Reynolds CEO of loop capital:

Among Reynolds' early employees was Craig Robinson, a former Morgan Stanley banker and Michelle Obama's brother. In his 2010 biography, "A Game of Character: A Family Journey From Chicago's Southside to the Ivy League and Beyond," Robinson recounted how he was going through a divorce while working at Loop.

Reynolds walked into Robinson's office and gave him a $5,000 check, saying: 'This is not a loan, and don't even try to pay me back.'

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.

"In 2003, James Reynolds, a Chicago investment banker who is a member of Obama's national finance committee, was recorded on FBI wiretaps arranging what prosecutors said was a 'sham' consulting contract with a woman they called the 'paramour' of a mayoral adviser in Philadelphia," USA Today wrote. "His firm later won $300,000 worth of city contracts."

In a statement to the paper, Reynolds pointed out that, after a thorough examination, no criminal charges were ever brought against him. "I can assure you, if the U.S. attorney's office believed that (my company) or I had violated any law, they would have brought charges," he said.

Today, Reynolds says again that after rigorous examination, "I was not a part of anything they wanted to investigate further