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Nearly six years ago, then Detroit mayor Kwame Kilpatrick was one of the most sought-after figures at the Democratic National Convention in Boston. This afternoon, Kilpatrick is making his second appearance in a downtown Detroit courtroom to explain why he can't pay the nearly $1 million that he promised taxpayers to resolve a sordid case that effectively ended his political career.

Kilpatrick's fall from grace was fast and hard. In September 2008, the youngest mayor in Detroit's history pled guilty to obstruction of justice and assaulting a police officer. He was sentenced to six months in prison. According to the terms of his probation, Kilpatrick resigned, pledged never again to run for elected office and surrendered his public pensions and law license. He also agreed to pay Wayne County, Michigan, which includes Detroit, a restitution of nearly $1 million. So far, Kilpatrick has paid about $90,000 of that sum. But despite having a $120,000-a-year job in Dallas with a subsidiary of Compuware, the billion-dollar software company based in Detroit, Kilpatrick now claims he cannot afford to meet the payment terms of his probation agreement. (Never mind his family's rented suburban mansion and flashy cars.)

Kilpatrick's story is, by any measure, tragic. He was born into one of Michigan's powerful political families. His mother Carolyn Cheeks Kilpatrick was until recently chairwoman of the Congressional Black Caucus. Tall and brawny, he played football at historically black Florida A&M University, studied law and rose quickly as a young representative in Michigan's legislature. By 2001, he was elected Detroit's mayor at age 31, partly by energizing this city's disaffected youth. His flashy suits, diamond-stud earrings and inaugural "club crawls" proclaimed his comfort with being called "America's first hip-hop mayor."

Initially, Kilpatrick maintained the confidence of Detroit's business establishment, extending many of the economic-development projects that were launched by his predecessor, Dennis Archer Sr. Kilpatrick moved thousands off Detroit's bloated job rolls and reduced property taxes to sustain what was left of Detroit's middle class. But Kilpatrick's personal excesses quickly overshadowed his professional success. In 2007, a jury awarded $6.5 million to two Detroit police officers who alleged that they were essentially dismissed for investigating concerns about Kilpatrick and his bodyguards' efforts to conceal his extramarital affairs. Then came a text-messaging scandal, which revealed that Kilpatrick and his chief of staff, Christine Beatty, had lied under oath about a sexual relationship that apparently had existed since their days at Detroit's élite Cass Tech High School.

Predictably, when Kilpatrick arrived for his first restitution hearing last month, it was a circus. He posed briefly for the spectators and gaggle of television cameras that were assembled in the courtroom. He was noticeably muted, wearing a gray coat, black pants and no earrings. Over nearly three hours, he was grilled by the lead prosecutor, Athina Siringas, and the judge, David Groner, on what should have been fairly ordinary matters, with questions like, Does your wife leave the house each morning to go to work? Shockingly, Kilpatrick said he didn't know. Groner then asked, "Who's paying the rent?" Kilpatrick responded with a simple, "Um," and then looked to his attorneys, Michael Schwartz and Daniel Hajji. "I assume my wife is paying the rent ... because I'm not."

Kilpatrick's attorneys tried to block the line of questioning, saying the former mayor, not his wife, must resolve his debts. One of their central arguments is that Kilpatrick's plea agreement allows the restitution to be adjusted to reflect 30% of his gross monthly income. Nevertheless, the exchange showed why it's hard to believe anything he says.

Perhaps the most surprising revelation during last month's hearing was that four of Michigan's wealthiest men — including Compuware CEO Peter Karmanos Jr., auto retailer Roger Penske and Quicken Loans chairman Dan Gilbert — had given a total of nearly $240,000 in loans to Kilpatrick's family around the time he left prison. Precisely how the money was used is unclear. The executives swiftly issued statements nearly identical in tone to explain their actions. "We were concerned about the city's inability to move forward due to the situation and circumstances that had surrounded Mayor Kilpatrick and his administration," Gilbert's statement read. The statement of Karmanos, Kilpatrick's boss, read: "We wanted to help care for his family until he could get back on his feet. At this time the loans remain outstanding."

It's hard to say what to expect at the hearing on Tuesday. Kilpatrick's saga has upended various aspects of Michigan's political and business life. His departure effectively set the stage for the arrival of Dave Bing, the former NBA star and steel magnate, who was elected to a full four-year mayoral term earlier this month. That a majority of Detroit's incoming city council will be fresh faces — including one of the police officials who triggered Kilpatrick's departure — can be viewed as a referendum on the former mayor's regime. Meanwhile, federal authorities are investigating other aspects of Kilpatrick's alleged activities. Respected lawyers hired to deal with Kilpatrick's mess are now fighting for their own careers. "I put my family through an incredible year of tremendous pain," Kilpatrick told reporters last month, clearly seeking sympathy. America loves a story of redemption. But Kilpatrick's constant excess, and his view that somehow he is above the law, makes absolution a difficult sell.

• Steven Gray / Detroit
• America loves a story of redemption. But former Detroit mayor Kwame Kilpatrick's constant excess, and his view that somehow he is above the law, makes absolution a difficult sell