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Oh 2012, what turmoil you brought to D.C. politics. Two councilmembers who started the year as elected officials are either in federal prison or under house arrest wearing an electronic monitoring device. Vince Gray appears to have weathered a summer storm that saw the U.S. Attorney’s Office allege that the mayor benefited from an illegal “shadow campaign” that helped him win the 2010 election. But the city still awaits what further moves, if any, U.S. Attorney Ron Machen is going to make. Machen’s been working so slowly against the mayor that if there were an award for slow federal prosecutors, Machen would be a shoo-in.

Wait a minute—awards! That’s not a bad idea! Presenting the 2013 Loosies:

The “We Are Never, Ever, Ever Getting Back Together” Award, Part 1: Vince Gray and Mary Cheh.

Is it ever okay to break up with somebody via voicemail? Gray didn’t appear to think so after his longtime pal, Ward 3 Councilmember Mary Cheh, left him a message in July saying she was going to announce that she wanted him to resign. Cheh joined Councilmembers David Catania and Muriel Bowser in asking for Gray to step down after one of Gray’s campaign aides pleaded guilty to being part of a vast “shadow campaign” that federal prosecutors say illegally helped win the 2010 mayoral primary. On TV shortly afterwards, Gray practically called Cheh a chicken for not telling him to his face. It was an awkward break-up for an awkward political friendship: Cheh initially supported Gray even though she represents an affluent, mostly white ward that heavily backed his rival, ex-Mayor Adrian Fenty, and thinks even less of him after nearly two years of being under federal investigation. By December, there didn’t appear to be any rapprochement between Gray and his erstwhile supporter. When Gray and Cheh disagreed on a city parking plan for disabled drivers, Gray’s spokesman told a reporter: “The woman is obviously confused.” And your boss’ feelings are obviously still hurt!

The Harbinger of Doom Award: Washington Post reporter Tim Craig

If you read a profile of an elected official in the Washington Post written by Tim Craig in which that official professes their innocence and expresses optimism that they won’t be facing any forthcoming criminal charges, you can set your watch for when those charges are coming.

Before Harry Thomas Jr. resigned his seat and pleaded guilty, Craig wrote about an upbeat Thomas feeling confident that he would beat any federal investigation. “I have good lawyers and people who deal with the legal process, and I am confident through the legal process I will be vindicated,” Thomas told Craig a few months before Thomas resigned at the beginning of this year.

This summer, as rumors swirled around the Wilson Building that then-D.C. Council Chairman Kwame “Fully Loaded” Brown was about to resign, Craig wrote another profile of an upbeat District pol confident that he, too, would prevail against the feds. “I’m not worried one bit,” Brown told Craig. Three days later, Brown resigned and was charged with bank fraud.

The Graceful Exit Award: Kwame Brown

The day before he resigned and agreed to plead guilty to a bank fraud charge, Brown must have been feeling a little tense. While WTOP reporter Mark Segraves was hounding Brown for a comment, Brown pushed Segraves against the wall. It wasn’t a full-on shove, but a push hard “enough to send a message,“ according to one witness.

Weirder still was that a few minutes later, as he was standing in front of the Council dais presenting a ceremonial resolution to a housing advocacy group, Brown began winking at Segraves, in what certainly looked to LL and other reporters like a taunt.

Brown later apologized to Segraves and said the winks were the result of a faulty contact lens.

The “Hey, That’s a Good Idea” Award: William Shelton

A week after Thomas pleaded guilty to using stolen city funds to buy an Audi SUV, William Shelton, a former chairman of Advisory Neighborhood Commission 5B, pleaded guilty to using stolen city funds to make payments on a Lexus.

The “We Are Never, Ever, Ever Getting Back Together” Award, Part 2: Vince Gray and Harry Thomas Jr.

Not long after Thomas’ guilty plea, Gray was asked if he’d recently spoken to his once-close friend and political ally. Gray responded: “If he called me up, I’d want to know, what is he calling me for?” At least he didn’t say he’d pretend he didn’t know who Thomas was.

The New Year’s Resolution Award: Vince Gray’s communications office

At the beginning of 2012, the mayor’s press shop set a number of goals for itself in order to improve its performance. One of those goals was to increase posts to the mayor’s official Twitter account by 20 percent, which translated to about one more tweet a day.

The Burning Piles of Money Award: Pete Ross

What’s worse than putting $200,000 of your own money into a primary campaign to win a seat as an unpaid “shadow” senator who has no staff and whose job is not officially recognized by any governmental entity except the District’s? Paying that much money, as Pete Ross did, and losing by 24 percentage points. (Full disclosure: Some of that money was spent on advertising in Washington City Paper. But that usually gets better results!)

The “Sometimes It’s Better Not to Be Meticulous” Award: Thomas Gore

Poor Thomas Gore. A close friend of Gray’s and the de facto campaign treasurer for his 2010 effort, Gore was such a good bookkeeper that he kept records on a spiral notebook of all the illicit payments the campaign was giving to nuisance candidate Sulaimon Brown. Once Brown went public that he’d been paid by the Gray campaign, Gore destroyed the records. That act, along with lying to the FBI, later lead Gore to pleading guilty to obstructing justice. The Gray campaign, by the way, wound up being Brown’s biggest single donor during the last months of the 2010 race.

The “Brand New, You’re Retro” Award: The shadow campaign

The alleged shadow campaign that federal prosecutors say illegally helped Gray get elected in 2010 sure had some old bones helping it. Jeanne Harris, who pleaded guilty to steering the $650,000 off-the-books effort, also pleaded guilty in the late ’80s to concealing two criminal schemes involving staffers for then-Councilmember H.R. Crawford.

In the mid-’90s, the control board demanded that Vernon Hawkins, a close friend of Gray’s who allegedly helped run field operations for the shadow campaign, be fired for “gross mismanagement” of Department of Human Services.

And in 2002, Scott Bishop Sr. was the fall guy for former Mayor Anthony Williams’ re-election campaign’s sloppy and illegal efforts to collect signatures to get on the ballot. Eight years later, Bishop says he was paid by Harris to hang signs for the Gray campaign.

The Right Place, Right Time Award: Phil Mendelson

The new Council chairman had no ambitions to move up from his perch as a relatively anonymous at-large councilmember last summer (or so he said at the time). But when Kwame Brown resigned, the Mendo era was upon us. He’s also next in line to become mayor if Machen ever comes up with something that forces Gray out of office. Not bad for a guy who people worried would lose his 2010 primary to Shadow Rep. Michael D. Brown only because his name was easily confused with Councilmember Michael A. Brown’s.

The Chutzpah Award, Part 1: Vince Gray

A few days after federal prosecutors alleged Gray was the beneficiary of the shadow campaign, Gray went after some law and justice of his own. His targets: immigrants who don’t speak English very well and sell marijuana paraphernalia from their convenience or liquor stores in low-income neighborhoods. Gray and his posse of city inspectors went store to store along Martin Luther King Jr. Avenue SE harassing store clerks who were selling individually wrapped cigars or pipes. “They don’t speak English well, but they understand this is an enforcement visit,” Gray said. They also probably understood it was a PR move by an embattled mayor.

The Chutzpah Award, Part 2: Vincent Orange

After Mendelson assumed the role of Council chairman, his colleagues had to vote on a temporary “pro tempore” No. 2. The ceremonial position doesn’t have any real power, but Vincent Orange wanted it badly anyway. Mendo and most of his colleagues wanted Michael Brown to get the gig, and Brown won the contest easily. But Orange didn’t go quietly. He launched a verbal attack on Brown, as well as a lengthy homage to himself that was so impassioned that even some of his supporters in the Council chambers were shaking their heads in amazement. “I’m the best, I’m the best,” Orange said at the crescendo of his performance. “Today, Vincent Bernard Orange Senior is the best candidate for chairman pro tem. The best.”

The Chutzpah Award, Part 3: Tommy Wells

The former social worker and current councilmember most associated with making the city friendlier to bikes and pedestrians, Ward 6 Councilmartyr St. Tommy Wells had this to say to a reporter about the status of his personal courage: “I know every corner of this city, go to places where police won’t go without backup.” Oh man, you’re one bad mother, Tommy Wells!

The Thin Skin Award: Jim Graham

Ward 1 Councilmember Jim Graham repeats as the most thin-skinned person behind the Wilson Building dais, and he will assuredly remain so for as long as he’s in office. This year was particularly rough for Graham, as questions over his conduct four years ago on the city’s lottery contract procurement came to a boil. An independent investigation by a law firm commissioned by Metro found that Graham acted improperly when he tried to leverage his spot on the transit agency’s board to pick winners on a development deal and the lottery contract. The newly formed Board of Ethics has launched its own investigation. Graham strongly denies all wrongdoing but never seems to have the time or inclination to answer any questions about the lottery—or any other uncomfortable subject.