He wears his title with pride and style - "mayor" is embroidered on the French cuffs of his fanciest shirts.
Kilpatrick was the man on whom the comedian Chris Rock modelled the hero of his political comedy Head of State, about a young black councillor, Mays Gilliam, who becomes president. "I was watching [television], and this guy comes on speaking. I didn't have the sound up, and I see the big earring, and I see this kind of loudish suit," Rock told GQ magazine. "Me and a friend - we were like, aah, this guy, what's he getting indicted for? And then we see he's mayor of Detroit."
Kilpatrick, like Gilliam, was voted in against all odds. He pledged to transform the image of the Motor City, which has lost half its population over the last 50 years along with its reputation as the industrial hub of the nation.
But with the mayoral primaries just 10 days away it is Kilpatrick's image that is proving a liability as his reputation for living a hip-hop lifestyle, including wild parties, lavish spending and a posse of wayward security guards, has left him struggling to keep his job.
"The problem is that all the stories have been about him and how he keeps acting up," says Ed Sarpolus, head of the polling firm Epic/MRA in Lansing. "Sooner or later the public starts saying, 'when are you going to start thinking about the city?'"
It didn't help that the stories were less than flattering. There were accusations that strippers were invited to the mayor's official residence, and that his bodyguards were drink-driving and failing to report accidents they were involved in. And then there was the "bling thing". He leased a luxury SUV for his family with city funds and lived large while travelling on city business with his mayoral credit card.
Kilpatrick initially denied all the allegations. But with the exception of the strippers and the drink-driving (he created another scandal by firing the policeman investigating those allegations), he ended up conceding many others, and paid back money he had spent on the mayoral credit card.
"I think some of them might have been exaggerated," says Kamau Marable, director of political communications and public affairs for the Urban Consulting Group in Detroit. "But those were the perceptions and perceptions have a way of becoming reality."
Kilpatrick has alleged a combination of racism and ageism. "If I was 60 years old," he told one newspaper, "if I came from the country club community, if I came out of an established private firm or something like that, none of these would get the lift that they have."
He is now avoiding the media, which he blames for distorting his image, preferring to communicate with voters directly through black radio and television spots in which he apologises for some of his behaviour and calls on the city to move on.
Views in the city are mixed. "I voted for him and I'd vote for him again," says Courtney Atkins. "I know he may have done some crazy stuff but I think the reason his SUV and spending is a problem is because young black men aren't supposed to have stuff like that. I mean aren't mayors supposed to have good cars?"
Others feel that the very thing he used as an attribute - his youth - has now become a flaw. "I think he was too young and too inexperienced," says a woman who gives her name as Sharon. "He employed his friends, who also had no experience. I think the job was too big for him and things got out of control.'
National views are similarly mixed. In the week that Time magazine named him one of the nation's three worst big-city mayors, Harvard University honoured him as the country's most innovative. Even his critics agree that Kilpatrick got many of the small things right - getting the grass mowed, the snow ploughed and the rubbish picked up - which so often tarnish municipal leaders' careers.
But tales of the high life have come at a low time for the city. Since the mid-60s the town that built the cars and made the music that shaped America's postwar culture has become the poorest and one of the most segregated in the country.
In the last six years Detroit has lost about a quarter of its factory jobs, leaving a quarter of its population in poverty. The city council, rather than the motor industry, is now the largest employer.
This decline started before Kilpatrick was born, but his critics say the situation has deteriorated on his watch. Faced with a $300m (£170m) deficit, he has had to lay off hundreds, eliminate jobs, cut pay and stop all overnight buses. Earlier this month the federal government came in to take over the local housing department. The fact that he is in the race at all is impressive.
He is currently running a distant second to his main contender, Freman Hendrix, in an open primary. Unless one candidate gets more than 50% both will go through to a run-off in November.
Hendrix believes the mayor's behaviour has become an issue because of the state of the city's finances. "If things were going just fine ... then people could look past all the living large and parting hard," he says. "But when there is real hardship that will rub anyone the wrong way."