The New Yorker has reprinted their articles about the Obamas over the years.
From a 1996 profile as part of a series about couples in America:
MICHELLE OBAMA: There is a strong possibility that Barack will pursue a political career, although it’s unclear. There is a little tension with that. I’m very wary of politics. I think he’s too much of a good guy for the kind of brutality, the skepticism.
From a story about his Senate campaign:
He was affable with everyone, smiling warmly, but in exchanges that lasted more than a few seconds it was possible to see him slipping subtly into the idiom of his interlocutor—the blushing, polysyllabic grad student, the hefty black church-pillar lady, the hip-hop autoshop guy. Black activists sometimes say that African-American kids need to become “bi-dialectic”—to speak both black English and standard English—to succeed. Obama, the biracial kid from Hawaii, speaks a full range of American vernaculars.
There are others. Read in sequence, it's an interesting series of snapshots, with the guy slowly coming into focus.