"What I thought was more interesting was that one of the knocks he had on me when he told me I was fired was that I was overeducated," he said. "That was more interesting than necessarily anything we had to do."

Trump's latest offensive on Obama has centered on his academic record. Obama was president of the Harvard Law Review, but Trump has demanded he release his school records to prove he was a worthy admission to the university and to Columbia, where he received his undergraduate degree. Allen noted that there are parallels between him and the president -- in fact, he even was a law student at the University of Chicago while Obama was a professor.

"I lived around the corner from where the President and his family then lived," he said. "I never took his class, but he was very active in the Black Law Students Association. ... He was very bright, very engaging, I was impressed even then."

Fortunately for Allen, other employers didn't share Trump's views on his qualifications. He now works in Washington, D.C., as business development director at Johnson Controls, helping businesses improve energy efficiency and sustainability levels in their buildings.

TPM asked Allen what he thought of Trump's comments that he's "the least racist person there is."

"It's an interesting statement, I doubt that its true," he said. "I think it's important to note given his comment that racism is not about just making racial slurs or about what you say outwardly, it's also a mindset and how you feel about folks and how you compartmentalize. It's interesting, I read his comment when he referred to how he has a great relationship with 'the blacks,' like it was some sort of alien population, which is a bit odd."

Ever the businessman, Allen sounded more interested in Trump's anti-Obama campaign as a marketing strategy than as a bellwether for his views on race. He told TPM that Trump "has a lot of great qualities and has obviously been very good at doing what he does" and noted that he's especially talented at messaging.

"The more negatives he can put out there about his competitor -- and if he's serious, that's what Obama is -- the better off he's going to be in terms of his ability to garner support from those who don't like Obama for whatever reason," he said.

An e-mail to a spokeswoman for Trump seeking comment was not immediately returned.