Wins a second term as Detroit Mayor and in 2006 is selected as Lieutenant Governor of Michigan by Jennifer Granholm over John Cherry, they are elected and halfway through her second term Granholm is selected for the Supreme Court/Attorney General/Sec Homeland Security by President-elect McCain and she resigns leaving Kilpatrick as Governor. He is re-elected narrowly in 2010 and goes on to defeat McCain in 2012 as an insurgent.
Well, no way that even the 'Maverick' McCain would choose that disaster Granholm for anything, but the ASB are flowing freely in this thread anyway.
I think the only way it could be done is without any bonus points. Possibly Kilpatrick doesn't have any scandals or dead strippers, primaries Granholm in '06, and defeats her with the horrible Michigan economy hanging around her neck. McCain defeats Hillary in '08. Obama wins Gov. of Illinois in '10, (
Game Change says that he hated the Senate.) and stays out of '12 to focus on his new job. Kilpatrick wins the Dem. primary when now very-disgruntled liberals choose him over Casey and Warner citing them to be "too moderate," and "too establishment," seeing that as the reason for the defeats in '04 and '08. Any Democrat will win the general election that year, though you could have McCain make and honor his one-term pledge to double down on that, if he still picks Palin.