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Earlier this year, Councilmember Vincent Orange was upset that his committee staff had to move offices. The relocation was prompted by new committee assignments, and several other councilmembers’ staffers also had to move. But Orange, according to several Wilson Building aides, was adamantly opposed to the game of musical offices.

How opposed? In one heated meeting Orange had with D.C. Council Chairman Phil Mendelson about the move, according to people present including Mendelson’s chief of staff Denise Tolliver, Orange compared Mendelson to a “plantation owner.” After about a week or two of refusing to move, Orange (who did not respond to multiple requests for comment) caved and moved.

That Orange would level that kind of attack on Mendelson over something so trivial may seem totally over the top, but it’s not totally unexpected. Mendelson, after all, is the accidental chairman who sits in the spot Orange has coveted for years. Orange has run unsuccessfully for chairman three times, and weighed running against Mendelson last summer after Kwame “Fully Loaded” Brown’s forced resignation. The pair also just don’t like each other: Mendelson once referred to Orange as an “embarrassment” from the Council dais, and Orange once lumped Mendelson in a group of “cowards” on the body.

What is surprising is the noticeably more aggressive stance Orange has taken against a natural political ally: Mayor Vince Gray. Orange and the mayor both came to office thanks to strong support among African-American voters in the eastern half of the city; they’ve shared many of the same campaign workers and financial backers; and they see eye-to-eye on most issues.

But in recent weeks, Orange has publicly questioned the honesty and integrity of senior Gray administration officials and accused the mayor of being a shill for out-of-town business interests.

“We are definitely very surprised by the hostility he is showing,” says one senior administration official, who was not authorized to speak on the record.

Much of the discontent between the two camps has played out in public. Orange showed reporters three weeks ago copies of a text message he’d received from Gray’s legislative liaison saying his opposition to a city contract “changes the landscape” of other measures Orange supported, which Orange says was a clear threat. At a Council hearing last week, Department of Small and Local Business Development Director Harold Pettigrew Jr. took a swipe at Orange with this (later deleted) tweet: “Amazing, those with poor leadership try to take shots at others to cover their own inadequacies and inability to effectively do their jobs.” Orange interrupted a hearing on a city contract to ask Pettigrew who he was talking about.

“It’s a tweet,” Pettigrew responded. “Just a leadership tweet.”

So where’s this all coming from? Some obvious answers include city contracting, mayoral campaign politicking, and Orange’s natural tendency to clash with those in charge.

Orange has long been the Council’s most vocal champion of the Certified Business Enterprise program, whose purpose is to steer city contracts toward local companies. He’s called every department head to testify in person before his committee about their spending on CBE-certified companies and personally intervenes on behalf of CBE companies (many of which are also campaign donors) that are having difficulties.

“Let’s make life a little more friendly for a long-time entity,” Orange told Pettigrew at a recent hearing after recounting how road-paving behemoth Fort Myer Construction had had problems with Pettigrew’s office.

So it was no surprise that Orange was displeased that Gray recently vetoed a bill aimed at boosting city spending with CBE companies, which Orange had authored and shepherded through the Council. Gray said Orange’s bill was an unworkable piece of legislation that would have stifled competition and diluted the value of the CBE program, and he called for the Council to start over. Orange reacted by issuing a statement accusing the mayor of having “caved to non-District-based business interests.”

Orange also tried to block a $12.7 million contract to hire consultants to revamp the city-owned United Medical Center because some of the losing CBE-certified subcontractors, including an Orange campaign donor, said the winning bidder hadn’t followed CBE laws when pursuing the contract. That was an unsuccessful and mostly lonely effort for Orange, as even his usual stalwart ally, Ward 8 Councilmember Marion Barry, sided against him. Barry tells LL he tried to warn Orange off of a losing cause: “I said, ‘Whose water are you carrying?’” From the Council dais, Orange said he was advocating on behalf of all the city’s CBE-certified companies.

“There’s a strong CBE-based consistency that he serves that looks to him to look out for its interests,” says a political advisor to Orange, who asked not to named because he’s not authorized to speak on the record. “There’s a political benefit in that.”

Ah yes, a political benefit. It’s little more than a year until the all-important Democratic mayoral primary, and Orange is sometimes included in conversations about potential candidates. (He ran, and lost, in the 2006 mayoral primary.) Setting himself against the mayor on CBE issues is not the worst way for Orange to boost his profile and lay a foundation for a mayoral run. It sure beats what Orange recently made headlines for: intervening in a city health inspection of a rat-infested grocery warehouse whose owner is a Orange campaign contributor. The newly formed Board of Ethics and Government Accountability is investigating whether Orange acted improperly.

But there’s a certain irony in seeing Orange try to position himself against the mayor. Their political futures, after all, are inextricably linked.

The key to this link is Jeff Thompson, the alleged financier of a “shadow campaign” the U.S. Attorney’s Office says illegally helped Gray win the 2010 mayoral primary. Thompson was also a major financial contributor to Orange’s 2011 campaign, possibly steering more than $100,000 toward Orange. Several donations linked to Thompson came in sequential money orders and had similar handwriting, which Orange himself later said looked “suspicious.” Other individuals who have been implicated in Gray’s shadow campaign played roles in Orange’s 2011 race, including Orange campaign advisor Vernon Hawkins and longtime Thompson associate Jeanne Clarke Harris.

Thompson has not been charged with any wrongdoing. But federal authorities have raided his home and office and Harris pleaded guilty last summer to campaign finance fraud.

Since those troubles began, Orange has tried to distance himself from Thompson. But previously unreported documents show that Orange’s financial ties with Thompson go back more than a decade and extend beyond campaign contributions.

When Orange was the Ward 5 councilmember in 2001, he started and ran a nonprofit to promote Emancipation Day and to support other charitable causes. According to a 2002 disclosure form Orange filed with the Office of Campaign Finance, he solicited donations from three entities to pay for a golf tournament, an awards gala, a gospel music festival, and a fireworks display. One of those entities was Chartered Health Plan, a healthcare company owned by Thompson, which donated $4,000 to Orange’s nonprofit, according to the OCF document. That’s small change from a long time ago, but it does highlight the fact that any future bad news for Thompson could hurt Orange’s political future.

CBE issues and future campaign maneuvering aside, there might be one other reason for Orange’s recent clash with the mayor: He just can’t help himself. Orange has a history of butting heads with authority figures. When he was a first-term councilmember in 2002, he raised his profile by forcing then-Mayor Anthony Williams to testify under oath about the fundraising shenanigans of his aides. And in 2005, he sued then-Council Chairwoman Linda Cropp over her refusal to allow him to hold a hearing on the Washington Nationals stadium. Cropp called Orange’s tactic “bizarre behavior” and noted that no other councilmember had ever taken a parliamentary procedure matter to court.

“It is my nature,” Orange replied, as he and Cropp sank to the bottom of the river they were trying to cross together.

Not really, but you get the idea.

Photos by Darrow Montgomery

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