Now, Obama has the devil's luck, which among other things means he has a boyish smile that disarms suspicion or hostility at 50 paces.And this stuff will come back to haunt Obama November,
But he is no child, and no innocent. Despite a childhood in Hawaii and Indonesia, Obama knows Chicago well - and from underneath, too.
He threw over a good corporate job in New York to toil in the dismal South Side as a "community organiser", getting up campaigns about asbestos in council flats but also getting to know this place's grimy, snaggled web of power - churches, property developers, professional politicians, fixers and money men.
He also revealed that he was the sort of person who goes into a revolving door behind you and then comes out of it in front of you. And, of course, he is a lawyer who knows the rules all too well.
As one veteran of Chicago politics who very much did not want to be named said to me: "Thank God for Louisiana - their politics are even dirtier than ours."
He clearly remembered Obama's first steps on his political career. This involved merciless cunning.
Somehow, all of Obama's challengers made a mess of their nomination papers. They were all disqualified. Only Obama's papers, miraculously, were perfect. So he won the Democratic nomination, which in this part of the world means he won the seat.
The insider recalled: "I thought he was a very talented young man. He was smart, he was willing, he was principled and he worked hard.
"He went to Springfield [the Illinois state capital] and did not become part of the more tawdry aspects of the culture down there - alcohol and women.
But Obama quickly got another reputation. "He was always in the bathroom for the really tough votes. It was not courageous."
The source explained this simply. Barack Obama knew even then that he could one day live in the White House.
"I think he understood long ago that the future was limitless for him. He made decisions in his very early political life that would enable him to be a candidate who would have very broad appeal."
These not-very-helpful remarks come from a black member of Obama's own party. What about his opponents?
It [Rezko's friendship] suggests very bad judgment, as do strong, persistent suggestions that Obama also accepted quite small contributions from extreme Left-wing veterans of the terrorist Weather Underground now living in Chicago.Just waiting for the Ayers Dorhn Obama photos to come out of the woodwork. Hopefully Obama had the good sense to cover his face Chicago style when the cameras came out for those.
His list of contributions shows one for $200 from a certain William Ayers. Can this possibly be the same William Ayers, now a Chicago professor, who used to plant bombs in the Seventies and has said: "I don't regret setting bombs. I feel we didn't do enough"? His partner, Bernardine Dohrn, once "declared war" on the US government.