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During his first term, his nicknames in the local media ran the gamut: "Big Diamond," "thug," "pimp," "player," "Kwame Soprano," "Swami," "his thugness," "ghetto," "gangsta," "inept club crawler," "hustler," "Puffy Kilpatrick." Often it was just plain ole Kwame—the reverent title of "Mayor," "Mr. Mayor" or "Mr. Kilpatrick" chucked aside.

Back then, stereotypical characterizations like that made me cringe and embarrassed for my colleagues in the news media. Now, as Mayor Kwame Kilpatrick announced his resignation and heads to jail, all I can do is just shake my head. He is fulfilling a prophecy the media laid out for him long before the indictment, before the jail stint, before he sent enough sordid text messages to his married chief of staff to fill a bookcase full of Zane novels.

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Black politicians of the world, especially the upcoming generation of leadership, please, please! Listen closely: Stop letting the media write your script! This was the message in the first chapter of my book, "Deconstructing Tyrone," a profile of Kilpatrick that doubled as a cautionary media tale.

During my time as a newspaper reporter in Detroit, I watched the city crumble as we focused on the most banal and trivial topics. Kilpatrick's wardrobe alone was enough to deliver a keynote address: There was the 1.5 carat diamond earring that for years flashed from his ear, which at the time was mentioned within the first 10 seconds of any news account of the then-wonder-boy mayor. He definitely oozed that Detroit flair, but drew the line at colored suits. "If I wore a red suit, it'd be on the front page of the papers," he sarcastically explained once. Apparently that did not rule out purple ties, pink handkerchiefs, electric blue stripes or classic Detroit gators. He used to step out with his sons in matching black suits and gold ascots—his fraternity colors. An asterisk to his florid style was a mayoral fleet that included a black Cadillac Escalade.

In other words, he hand-delivered chalk to caricature artists. Chris Rock has said he partly used Mayor Kilpatrick as a model for his role as the first black president in the movie "Head of State." But in the short stint that I covered him a few years ago for The Detroit News, while reporting on the Detroit City Council, I came to see other images: A father of three, former schoolteacher married to his college sweetheart. I found a self-described "citizen of the world" who loved to quote the Bible. A lawyer. A man of privilege who refused to turn his back on his hometown.

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But Kilpatrick and I were both members of the post-civil rights generation, so I didn't make too much of his hip-hop style. Our relationship over the short time I covered him was good-humored, given our antagonistic roles. ("You eat pork?" he once asked incredulously during a breakfast interview, skinning his face as though I'd slaughtered the pig with my bare hands. This, after he ordered enough food for two starving people.)

Politicians are bound to have tension with the media performing a watchdog role. But many black politicians don't seem to understand that part of their job is media relations. After being elected to positions of power, black politicians often reflexively assume a beleaguered stance, which is understandable, given the historical representations of blacks in the media. But many of them seem to forget that the whole point of electing black leaders is for them not to be helpless actors, but to wield power and influence, yes, even with the media.

Contrast the Kilpatrick train wreck with Sen. Barack Obama's handling of the Rev. Jeremiah Wright controversy. Obama saw the ball was going in the wrong direction in the ridiculous debate over Wright. Instead of whining in Philadelphia, Obama took the opportunity to stop the ball, turn it around and deliver a landmark address on race. Unfortunately, this kind of approach has been more the exception than the rule. As a whole, black politicians are surprisingly naïve and often willfully ignorant of the way media works. And they either don't care or don't realize that their ethical gaffes play right into the media's hands.

And so it was when Kilpatrick breezed into office in 2002. At first, the local and national media descended and fawned over his youth and vision for a new Detroit. An article in The Christian Science Monitor assessing his first six months in office was representative: "Hip-hop mayor aims to rev Motor City engine," the headline read. The youngest big-city mayor was described as "bold, charming, direct and determined to succeed….he's taken on his job with all the vigor and—some would say—bravado expected of someone his age."

There was a brief moment of optimism that comes with reporters who are hungry to hear new political voices. Kilpatrick snatched some upbeat coverage during the 2004 Democratic National Committee convention in Boston when he was chosen to share the stage on national television with Sen. John Kerry after the presidential candidate's speech.

Back then, Democratic strategist Donna Brazile said Kilpatrick was a source of inspiration to the party because of his understanding of urban issues. In 2005, the Initiative for a Competitive Inner City, founded by a Harvard University professor, awarded Kilpatrick with the top city award, based on business ventures in the urban core.

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But the honeymoon didn't last long. Soon reporters were swooning when he lied about buying his wife a Lincoln Navigator with city money. In early 2005, it could've been a one-day story about the $25,000 vehicle—if the mayor hadn't lied about it. Everyone could have kept it moving to deal with the bigger issues, namely the city's finances. The storyline about his cherry-red Navigator carried on for more than a week, and that symbolism would stick.

Kilpatrick's denial and handling of the stupid Navigator story gave respectability to an obnoxious television "reporter" for the local ABC affiliate, a Michael Moore knockoff who stalked the mayor like a one-night stand who didn't get the hint. "Oh my goodness," the mayor said under his breath after being confronted with the reporter in a stealth ambush in Washington, D.C. He'd be happy to give an interview, Kilpatrick told his plump nemesis as a camera rolled. "We can go liiiiive, anytime," Kilpatrick taunted eight times, jabbing his finger in the air. Watching their pissing match escalate into a series of television reports in which said reporter was shoved into a wall by a member of the mayoral security detail, you're thinking, this can't be good for democracy.

Eventually, it dissolved into farce. "Quit hiring prostitutes," the mayor told the ABC guy as cameras chased him through the streets of Detroit. Then Kilpatrick gave this parting shot for good measure: "Fat-ass."

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Maybe Kilpatrick was just following the example of his civil rights generation predecessor, Detroit Mayor Coleman Young. During his two-decades-long reign, Mayor Young cussed on a dime and had a strained relationship with the mainstream media. But while Young had more than his share of media run-ins, he had been in office long enough to build support among residents and build alliances that helped him to do his job.

In contrast, Kilpatrick's whole tenure was focused on scandal. When the rumors surfaced of a wild party at the mayoral mansion, Kilpatrick played the role of the media victim in a 2003 interview with The New York Times. "If I was 60 years old, 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 told the reporter. "I guess it's believable that a 32-year-old black man with an earring in his ear has parties like that. It's so unfortunate. I'm here to fight that stigma." In a 2004 speech about the state of black boys, the media whining from Kilpatrick continued: "We believe the traditional things said about African-American men…philanderer, thug, hang with drug dealer."

He's right. There is a double standard, but savvy politicians accept, even cuddle, that paradigm and proceed accordingly. In the end, what did Kilpatrick do? Philanderer? Check. Felon? Check.

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With his latest turn of fortune, I feel for Kilpatrick's family. But what can't be ignored is the dire straits the Motor City is in. When politicians and the media become consumed by steamy headlines while ignoring the nuts and bolts of good government, it is the public that suffers. It is a lesson that should be applied on the national stage, as well.

In the meantime, everyone seems to be perfectly happy to ignore the city of Detroit's toilet-flush spin. Sadly, that will be the real legacy of Detroit's so-called hip-hop mayor.

Natalie Y. Moore is a reporter at Chicago Public Radio. This article was adapted from "Deconstructing Tyrone: A New Look at Black Masculinity in the Hip-Hop Generation."