He doesn't. He has an affected Chicago accent, much like someone who moves to the South will take on a slight accent.
Personally, I cringe every time he says words like "jobs" since he sounds like he's imitating Dan Akroyd playing Elwood Blues.
Yeah but I don’t get it. I lived in Scotland for 3 years starting when I was 35 and I didn’t come back sounding like William Wallace. Never lost my New Yawk accent. Is it a Madonna like thing with this guy, complete bulls**t? Madonna lives in England for 2 seconds and comes back talking like Keira Knightley. Yeah right baby. Try the con again. How long did the Kenyan live in Chicago anyway? Also has anyone thought of checking out his status with INS? It’s quite possible he could have an expired student visa. But let’s not even look for that, let’s just see his record with the INS or is that shut off as well? I can’t see how due to the freedom of information act.