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A week after Mayor Vince Gray won last year’s primary election, he had a meeting with U.S. Attorney General Eric Holder. After the meeting, Holder surprised reporters by telling them that he had voted for Gray. By contrast, Gray’s own attorney general, Irv Nathan, has declined on several occasions to say who he voted for (probably because he voted for the other guy).

“I’ve known the chairman for a good number of years,” Holder told reporters. “I think he’s going to be a great mayor and I look forward to continuing that relationship.”

That relationship, and one Holder has with D.C. Council Chairman Kwame “Fully Loaded” Brown, could soon get awkward as everyone in District politics makes throat-clearing noises about the need to do something about the perception that the Wilson Building has seen more ethical days. Councilmembers will almost assuredly pass some sort of ethics legislation soon; they can hardly go into an election year without looking like they’ve tried. But they’re also unlikely to want to crack down aggressively on the practices that can give incumbents advantages, so don’t expect tighter campaign finance laws, or a ban on outside employment, or term limits.

What the council will most likely focus on is the requirements for disclosing, and preventing, conflicts of interest and the appearance of conflicts. Which is where Holder comes in. A former U.S. Attorney for the District, Holder has deep links with the city, and people have talked him up as a potential mayoral candidate for years. He also has ties to some of the District politicians, like Gray and Brown, who are currently being investigated by federal prosecutors—who ultimately report to Holder.

No one—not even LL—is suggesting that the attorney general would try to tip the scales of a federal investigation into District politics. But if you were trying to scrub the system of any and all appearances of conflicts of interest, some experts in government ethics say, you probably wouldn’t want Holder to be in charge of the people investigating his buddies.

For instance, campaign records show Holder donated $500 to Gray’s campaign two days before the primary. That campaign, we all know by now, has been subjected to what appears to be a very through investigation by federal investigators, looking into accusations by minor mayoral candidate Sulaimon Brown that Gray aides paid him cash and promised a job in return for attacking former Mayor Adrian Fenty.

Holder also has ties to Kwame Brown, whose 2008 campaign the D.C. Board of Elections and Ethics has been practically begging the feds to investigate for financial irregularities. (An audit found Brown’s campaign directed $240,000 through a third-party contractor to a firm owned by Brown’s brother, and $170,000 of that money hasn’t yet been accounted for.) BOEE Chairman Togo West, a former secretary of the Army, told reporters he believed Brown’s campaign engaged in “criminal activity.”

This January, Holder swore Brown into office. Their relationship dates to at least 2005, when Holder was part of a group of potential owners of the Washington Nationals looking for council support. Indianapolis businessman Jeffrey Smulyan was looking to overcome the stigma of being an out-of-towner and boost his chances of nabbing the Nats. So he teamed up with a group of local and minority investors, including Holder, who was in a private law practice at the time. Smulyan’s bid ultimately failed, but his move to include Holder did garner at least one councilmember’s backing.

“How could you not support a group with people like…Eric Holder?” Brown told the Washington Times at the time. “These are people who have been in the city for a very long time and have made significant contributions to the city, and for them to have equity ownership in the team is important.”

Holder didn’t give to Brown’s campaign, but his old law firm, Covington & Burling, did give $1,000 in 2007. That donation was for Brown’s 2008 re-election campaign, the one federal authorities says they’re currently looking into.

Exactly where things stand with any federal probes isn’t clear. Whereas Gray supporters have grumbled about the feds being overly aggressive in pursuing the mayor’s campaign, no one’s saying how much energy they’ve put into looking at Brown. It could be a lot, it could be a little—but it’s worth noting that several former Brown campaign workers LL spoke with say they’ve not been contacted by authorities.

So for a District trying to burnish its ethical reputation, are these types of connections between Holder and city officials something to worry about?

The normally verbose Paul Craney, executive director of the D.C. GOP, is judicious in his comments. “The perception could be growing among certain people that not enough is being done,” he says. “It’s the cozy factor; something needs to happen soon.”

Two academics who spend time thinking about this kind of thing were a bit more blunt. Stephen Gillers, a legal ethics expert and law professor at New York University, says Holder’s declaration that Gray would be a “great mayor” could pose a problem were Holder to get involved in the investigation. “Holder can now be seen to have an interest in vindicating his prediction.”

Lawyers familiar with how these things work say there’s little chance Holder would be personally involved in either case. A spokesman for Ron Machen, the current U.S attorney for the District who is investigating both Gray and Brown, declined to discuss the “mechanics of charging decisions.” But a spokeswoman for Holder said that these types of “prosecutorial decisions” are made at the local level.

What about the line prosecutors assigned the cases, might they not want to risk making their boss look bad by prosecuting his pals? Fat chance, says Fred Cooke Jr., the go-to defense attorney for District pols in trouble. Cooke, who currently represents Brown, says federal prosecutors aren’t the types to be swayed by their bosses’ connections. “You’re dealing with Type A personalities,” says Cooke. “They’re looking out for numero uno.”

But George Washington University law professor Jonathan Turley says there’s still “no question” of an appearance of a potential conflict of interest. At a minimum, Turley says, Holder needs to make a very public statement saying he will have nothing to do with Gray and Brown’s cases. Such a move would not only reassure the general public, says Turley, but the career prosecutors assigned to the cases as well.

Don’t expect any type of public statement from Holder soon, though.

“Anyone that thinks that we would go light on somebody because of a relationship doesn’t know the attorney general and doesn’t know me,” Machen said recently on the Kojo Nnamdi Show on WAMU. “That’s not how the man operates.”

Ah, but is it not? A glance through the archives shows that when Holder’s three and a half year stint as the District’s top federal prosecutor ended, the summaries of his career all held a common criticism: He was soft on public corruption.

Del. Eleanor Holmes Norton was quoted in Washingtonian saying that the U.S. Attorney’s Office under Holder “obviously hasn’t been aggressive enough” in pursuing D.C. officials. And a Washington City Paper profile lambasted Holder for being afraid to take on then-Mayor Marion Barry, saying Holder had “precious little impact on the city’s endemic municipal corruption.”

At the time, Holder rejected that criticism and echoed the same lines that his office and Machen say now: that they follow the facts wherever they lead, regardless of politics.

And that’s almost certainly true…right?

Photos by Darrow Montgomery

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