Kwame Kilpatrick’s resignation as Detroit mayor is effective September 18, but the city will be dealing with the legacy of his administration for years to come. Kilpatrick agreed to resign as part of a plea agreement on charges of perjury, obstruction of justice, and official misconduct, filed after hundreds of sexually explicit text messages, printed in local papers, proved that he had committed perjury when he testified in a civil trial that he had not had an affair with his chief of staff, Christine Beatty. The case involved more than run-of-the-mill lying about adultery, however. In fact, it was consistent with a continuing pattern of Kilpatrick’s abuse of office.

The civil lawsuit was brought by two Detroit police officers who claimed that the mayor retaliated against them after they investigated alleged wrongdoing by his police detail. The pair won a $6.5 million jury verdict; after vowing to appeal, Kilpatrick offered an $8.4 million settlement—that’s right, more than the jury verdict—if the plaintiffs would agree to keep the text messages confidential. He then tried to strong-arm the city council into approving the settlement, without notifying the council about the confidentiality agreement or admitting his affair. The officers’ charges came after years of complaints about Kilpatrick’s abuse of mayoral perks, his habit of verbally and even physically assaulting reporters who irritated him, his interference in police investigations, and his commandeering of city resources for personal use. (Among the unflattering stories reported by the local press was Kilpatrick’s habit of whipping through city streets on a motorcycle he requisitioned from the police motor pool.) This past spring Kilpatrick was accused of assaulting a process server. As part of his deal with prosecutors, he pleaded no contest. But the nadir of the eight-month drama that paralyzed the city’s political life came in August when, after being charged with assaulting a sheriff’s deputy, the Democratic mayor of Detroit was fitted for an electronic ankle bracelet.

The farce of Kilpatrick’s trial and resignation has only further tarnished Detroit’s already dismal national reputation. But for many, the saddest result has been the squandering of Kilpatrick’s potential to be a great big-city mayor, one who might have led Detroit out of the wilderness and helped recapture its lost glory. Kilpatrick was the youngest mayor in Detroit’s history, winning office at just 31, and he brought a sense of youth and vitality to the administration of a city that had become a symbol of rust-belt decay. “He was often brilliant, a charismatic leader who could charm investment dollars out of the business community and serve as a bridge across regional and cultural borders,” wrote columnist Nolan Finley in the Detroit News.

Unfortunately, even putting aside the scandals, Kilpatrick’s stint in office was largely a failure. He balanced the city budget and avoided receivership, but only by relying on casino revenues, by raising property-transfer and fast-food taxes—this in one of America’s highest-taxed cities—and by floating long-term bonds that ignored the structural deficiencies in the city’s budget. (On his retirement in 2005, former city auditor Joe Harris blasted Kilpatrick for his “tunnel vision and myopia” in relying on unrealistic revenue assumptions, and for good measure called the city council “one of the most divisive and ineffective legislative bodies of this City within the past several decades.”)

Detroit was awarded the 2009 NCAA Men’s Basketball Final Four, for which Kilpatrick claimed credit, and his administration also touted the renovation of more than 80 buildings downtown, though it’s unclear how much influence he had in either development. Perhaps the largest gap between rhetoric and reality came with Kilpatrick’s “NEXT Detroit” initiative, a five-year effort to revitalize six inner-city neighborhoods. The effort has so far produced dozens of public meetings, a number of feel-good PR events, the issuance of multiple strategies and vision statements and blueprints—but few actual results. Two possible reasons for the lack of success: NEXT Detroit planned for $100 million in nonprofit and corporate backing that was never forthcoming, and the initiative was run by Chief of Staff Beatty, who as we now know was otherwise occupied.

What makes Kilpatrick’s abuses and failures especially heartbreaking is that they set back a city that was beginning to show at least tentative progress in revitalizing its crumbling infrastructure and restoring its blighted city center. Detroit’s woes are well known: a 9.7 percent unemployment rate, the out-migration of 175,000 residents since 2000, and a violent crime rate nearly three and a half times the national average (and more than five times the national average for murders). While hardly an exemplar of urban reform, Kilpatrick’s predecessor in the mayor’s office, Dennis Archer, had brought the city’s budget process under some semblance of control and reached out to suburban leaders who had long been downright hostile to the city. Since 2000, Detroit has even experienced a baby boom, with 430,000 children born in a period in which only 280,000 residents died.

It was in exacerbating racial divisions that Kilpatrick may have done his city the greatest disservice. Kilpatrick was dubbed “the hip-hop mayor,” sporting a diamond stud earring and surrounded by a huge rap-mogul-style entourage. True, Kilpatrick resisted some of the wilder excrescences of Detroit racial politics, vetoing a council-backed “Africa Town” proposal in 2004 that would have spent $40 million on the creation of an African-American business district. But once under investigation, Kilpatrick played the race card frequently. In 2005, a third-party group associated with his reelection campaign compared media investigations into his affair with a lynching. When he lost the whistleblower suit that would ultimately prove his downfall, Kilpatrick blamed white suburbanite jurors and added, “There’s race in this, and we run from it in this region. And I think it’s impossible for us to move forward as a region without confronting it head-on.”

And then, in his 2008 state of the city address, he shocked listeners by departing from his prepared text to claim that “in the past 30 days I’ve been called a nigger more than anytime in my entire life. In the past three days I’ve received more death threats than I have in my entire administration. . . . This unethical, illegal lynch mob mentality has to stop.”

Now, finally, after holding the city hostage for months as his personal legal troubles played out in the media and in court, Kilpatrick is headed for jail. It’s unclear, though, whether he is out of the city’s political life for good. “I want to emphasize tonight that I take full responsibility for my actions,” he said the night that he pleaded guilty. But his address was more stump speech than mea culpa, and he praised his administration’s accomplishments while lashing out at critics such as Michigan governor Jennifer Granholm. And then he ominously predicted a return once his five-year probation ends: “This city always gets up. I want to tell you, Detroit, that you done set me up for a comeback.” After six years of Kwame Kilpatrick, Detroit residents might wonder whether the office of mayor has any value left at all.

Justin Torres is a writer and attorney.