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Michael Brown had problems. He owed $1.46 million on his mortgage, an amount that had ballooned by nearly half its original size thanks to late fees. Brown had to make countless other payments to keep up his image as a successful at-large councilmember—-a golf course membership, hotel stays, fancy shopping trips, even mortgage payments for other people.

In July 2012, Brown decided to get some relief from his bills by accepting bribes from two Maryland businessmen in exchange for help getting them District contracting certifications. As Brown and the District would learn, the businessmen were actually undercover FBI agents. The solution to Brown’s problems had made them all much, much worse.

In a sentencing memorandum filed today, prosecutors paint Brown as a man so obsessed with appearances that, even after pleading guilty, he disguised help from shadow campaign maestro Jeff Thompson from investigators to preserve the integrity of his one successful campaign. In the document, prosecutors ask for Brown to serve the full 43 months of Brown’s plea and say a whole lot of mean stuff about him along the way.

In their own filing, Brown’s lawyers ask for him to receive an unspecified sentence that’s less severe than the 37 months outlined as the lower end in his plea agreement when he’s sentenced on May 8. Brown turned to crime, according to his lawyers, only because “traditional lending options [were] closed off to him.”

The prosecution isn’t so generous. Growing up with benefits of a well-connected family as the son of former Secretary of Commerce Ron Brown, prosecutors write, Brown can’t claim the deprivation that drives other men to crime.

“But when it came to the qualities that should matter most for elective office—honesty and integrity—Michael Brown was simply unfit for the political heights he had reached,” the memo reads. “A review of Defendant’s character demonstrates that, in spite of the many advantages and opportunities he was afforded throughout his life, Defendant nevertheless chose to walk a path marred by shortcuts, easy money, and corruption”

Despite earning a yearly salary between $180,000 and $300,000 since 2007, prosecutors write, Brown was always low on money. They blame his spending on an attempt to maintain an “affluent image,” with money being the only thing that gave his life “balance.”

“The problem, and it was a problem of his for a long time, was that he never had enough money,” the memo reads. “And so his life—personally and professionally—was in a perpetual state of imbalance.”

Both Brown’s attorneys and the government agree that he helped with the federal investigation into city contractor and illicit campaign backer Thompson, who pleaded guilty on March 10. Brown, like Vince Gray, apparently also knew Thompson’s “Uncle Earl” code name.

Still, while he admitted receiving illegal help from Thompson in his 2007 Ward 4 Council run against current mayoral candidate Muriel Bowser, Brown didn’t tell prosecutors that Thompson had also backed his 2008 at-large run. Brown only admitted to the scheme after prosecutors confronted him with evidence of it, a deception that could cost him another six months in prison. Prosecutors theorize that Brown, headed to prison anyway, still didn’t come forward with that crime because it “brought more personal shame to him, [and] tainted the only City-wide election Defendant ever won.”

Asking for leniency, Brown’s lawyers point to his help with investigations into Thompson, the lottery contract award, and the federal pursuit of Hakim Sutton, a former Brown campaign treasurer charged last month with stealing from Brown’s unsuccessful 2012 re-election campaign to fund his own jetsetting lifestyle. In a coincidence that likely doesn’t seem that funny to Brown, he met with investigators in 2012 to help them pursue Sutton even as other investigators were drawing him further into their sting.

Brown’s lawyers also take a jab at fellow Thompson shadow campaign beneficiaries like Gray, pointing out that Brown is the only public official who’s admitted to knowing about Thompson’s illicit help.

Letters in support of Brown come from Brown family members as well as friends including the Rev. Jesse Jackson, Black Entertainment Television CEO Debra Lee, and former Gray spokeswoman Linda Wharton Boyd. The letters reveal a personal side of the former councilmember—-Brown has apparently become a fan of watching The Young & The Restless with his ailing mother. Brown’s sister writes that he’s a fiend for “would you rather” questions like “Would you rather eat a slug, chewing it slowly, or a large bowl of mayonnaise?” (That’s easy, councilmember—-the mayo!)

Brown’s son Morgan Brown submitted his own letter in which he talks about how his father’s plea dashed his own plans to extend the family’s political dynasty for another generation.

“I planned on going to law school and becoming a city council member in DC, just like him,” Brown’s son writes. “Now I am sad, disappointed and worried.”

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Photo by Darrow Montgomery