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Jack Evans has only been campaigning for two weeks, and already here he is, debating corporal punishment.

The Ward 7 Democrats’ regular Saturday morning meeting on June 22 had been consumed for the last hour by talk about why the ward’s young people couldn’t get jobs. Eventually, though, one man proposes a bizarre solution: Why not just let teachers hit kids in D.C. public schools?

Evans does not actually think that’s a good idea. On the other hand, he’s running for mayor, and he can’t really tell a roomful of voters that some of them are nuts. He settles on a compromise: Hitting may have looked like a good idea decades ago, but these days, not so much.

The crowd’s mollified, and the would-be mayor gets a reward. An elderly man stands up and tells Evans that he likes him, if only because he’s put in his dues.

Evans, who represents Ward 2 on the D.C. Council, has put in more than dues than anyone else in the race. After being on the job for 22 years, he’s the longest-serving councilmember. He’s even run for mayor before, trying to pull off this same thing 15 years ago.

It didn’t work then. This time is different, but not always in ways that work in his favor. And it might be Evans’ last chance to convince the city that it deserves him.

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A week earlier, Evans had kicked off his campaign in front of 14th Street NW’s Le Diplomate. A buzzy French bistro, it’s a place so tony that the idea of Evans—the presumed favorite of the city’s wealthy—holding his campaign launch there seems too oblivious, too Thurston Howell III to be real.

But hold it there he did. His ambitions were equally lofty, with Evans promising to make D.C. a world-class city to compete with great European capitals. “Quite frankly, my vision is what we need in order to establish the District of Columbia as one of the great cities of the world,” Evans says.

With 14th Street as his backdrop, Evans’ message was clear: Look what I did.

When Evans launched his last mayoral campaign in this neighborhood, the District wasn’t hoping to compete with Paris. Even regaining basic city functions from the Financial Control Board then in charge would have counted as a huge victory for any mayor.

That effort launched on Evans’ birthday, Oct. 31, 1997. Evans chose to launch from a Logan Circle playground that doubled as the site of gang killings. Months later and a few blocks further south, Evans, then the chair of the Council’s public safety committee, would stand in June 1998 with then-Metropolitan Police Department Chief Charles Ramsay while a leather skirt-clad prostitute walked up to them and told them they couldn’t do a thing to stop her.

Evans’ messaging at the time was just about as gloomy as 14th Street’s red-light district. At debates, he joked that his mayoral duties would be limited to keeping city pools open, unless he could convince Congress otherwise. At other debates, he was booed by crowds opposed to his support for a new convention center. On then-Mayor Marion Barry, Evans didn’t pander: Barry’s legacy was “horrible.” Evans had a plan to make things better, but first, he needed to be mayor.

Evans outraised his early competition, fellow “Young Turks” Council reformers Kevin Chavous and Harold Brazil. He built a massive campaign machine, pulled together by politically wired manager Warren Graves. All that organizing paid off—one Post story from the election has Evans showing up at a picnic with a 40-member marching band, complete with Evans shirts, in tow.

Two things stood in Evans’ way. The first was race. In 1998, Jack Evans—blue-eyed, pale—was very white in a city that wasn’t. A poll found that even a third of likely Evans voters thought it was at least somewhat important for the District to have an African-American mayor.

“At that time, liberal whites in this city weren’t going to support a white candidate. You know, he had blond hair,” says Leroy Thorpe, a Shaw activist and former ANC commissioner who switched his support from Evans to Chavous when he realized—correctly—that D.C. wouldn’t elect a white mayor that year. (Thorpe would know about Evans’ hair. At one point in 1998, he called Evans a blond-haired cracker.)

Evans tried to joke about his near-absolute lack of melanin, but that only seemed to make things worse. After being mocked for a 1997 holiday card featuring his all-blonde family with a golden retriever, Evans sent out a campaign mailer the next year with himself and African-American children on a playground, only drawing more attention to the whole dynamic. “Evans is either the most racially insecure politician around or, as critics say, he’s up to no good,” Post columnist Colby King wrote.

Still, you never know what could happen in local elections, and maybe Evans might have pulled it out if not for his second problem: Tony Williams, the control board-appointed chief financial officer for the District. After jumping into the race late, Williams swept into office as the only candidate who hadn’t been somehow involved in making the District’s finances the catastrophe they were.

“The dynamics of that race were three incumbent councilmembers, all of whom had been on the Council for a while, and Tony Williams,” says former Councilmember Sharon Ambrose, who backed Evans in 1998. “And Tony Williams just flipped it.”

Williams’ late entry didn’t stop him from gobbling up Evans’ supporters. Evans lost the Board of Trade’s endorsement, once thought to be a sure thing, to the CFO. Then Williams’ supporters blocked Evans from getting the endorsement from District gay groups and even his own Ward 2 Democrats.

In the end, Evans came in third behind Williams and Chavous, with just 10 percent of the vote in the Democratic primary. Jack Evans had tried to run D.C., but instead, voters had embraced someone newer than him—and, to make matters worse, someone originally foisted on the city by Congress.

It was the first sign that Evans’ political career might not always be as charmed as it had been. Evans, originally from Nanticoke, Pa., had come to the District in 1978 with a law degree from the University of Pittsburgh and a job offer from the Securities and Exchange Commission.

After moving to Dupont Circle, Evans ran for an Advisory Neighborhood Commission seat because of an interest in politics. Evans—at the time 38 years old, single, and living in the center of gay life in the city—says there were questions about his sexual orientation, but his fellow commissioners weren’t fooled; he recalls one of them, after visiting his home, saying that no self-respecting gay man would have such an ugly couch.

After joining the ANC, Evans became the protege of John Wilson, the then-Ward 2 councilmember, who would commit suicide in 1993 while serving as chairman. (A picture of Wilson with the caption “I miss John Wilson” has a prominent place in Evans’ Council office, no small feat given how crowded Evans’ walls are with pictures of him with celebrities.) When Wilson became chairman, Evans ran for his seat in 1991, beating opponent Jim Zais in part by appealing as much to the gay community as Zais, who was gay, did.

These days, besides his ardent support for developers and development, Evans may best be known as the poster boy for the debate over whether councilmembers should be able to have outside jobs. He makes $190,000 a year working for powerhouse lobbying and law firm Patton Boggs. Aside from disclosing his salary, though, Evans doesn’t have to reveal much about what he’s paid for.

Evans has escaped the recent high-profile ethical lapses that have befallen his Council colleagues, but his own scandal came in 2005, when reporters uncovered that a political action committee Evans controlled—“Jack PAC”—was legally taking unlimited donations from developers and parking companies. One billboard company alone gave $10,000. The money paid for things like dinner and sports tickets for Evans—including $1,325.73 for Evans to travel to Nationals’ spring training.

The PAC also reimbursed Evans $6,772.72 for a trip to China, which included the expenses for a friend to travel to China with him in October 2004. After an Office of Campaign Finance report that cleared Evans of any law-breaking recommended that he pay for the China trip, he complied. Now, Evans says he’s surprised by how much attention the PAC received.

Jack PAC is no more, but Evans still pays for season tickets to local sports teams with his constituent service fund. Between 2002 and 2011, the fund spent $135,897* on tickets for Wizards, Kastles, and Nationals games, according to a Washington Post review of campaign disclosures. Evans defends the practice, saying he gives many of the tickets away to help out residents who couldn’t afford to attend otherwise.

Fifteen years is a long time in D.C. politics. The African-American population so crucial to determining the outcome in 1998, while still important, dipped slightly below 50 percent in the latest Census. The District electing a white mayor doesn’t seem as impossible as it did in 1998.

Evans points to the election of white Detroit Mayor-elect Mike Duggan as evidence that D.C., too, could elect a white person. “Throughout the country, I think people are more accepting of people not from the same race,” Evans says.

Things have changed for Evans personally, too. His triplets, who were 18 months old when he ran the last time, have morphed into teenagers. He’s flanked at Le Diplomate by his second wife, Michele Seiver. (His first wife, Noel, died in 2003.)

The politically connected staffers who ran Evans’ last campaign are nowhere to be seen. In their places stand much younger, 20-something campaign workers, many of whom got their start in District politics working on Anita Bonds’ successful at-large campaign last April.

Evans’ staff’s youth shows in his campaign, which tweets out vaguely meme-ish graphics with quotes from Evans, even if the quotes themselves (“A government shutdown is irresponsible—Jack Evans”) aren’t exactly burning up the servers.

Evans 2014 continues elsewhere online, too. Evans’ interns—er, “fellows”—fight the good fight on his Wikipedia page, evading site administrators wary of editors with conflicts of interest. With the help of the fellows, a bland passage on Evans’ advocacy for Nationals Park becomes, “Evans believes in the ability of sports to improve communities.”

Then there are the signs. Evans’ red-and-white posters have been the most visible of the 2014 mayoral race so far, appearing with a Silicon Valley twist: instead of slogans, the signs display Evans’ name and Twitter- or Instagram-friendly hashtags like “#jobs” or “#safestreets.”

Anyone who’s been on Twitter for more than five minutes knows that the Evans campaign’s use of hashtags is, in practical terms, insane. Searching for a hashtag as common as “#jobs” on Twitter or Instagram will bring up thousands of messages from people who have never heard of Jack Evans and don’t live in D.C. They seem like an idea cooked up by someone who’s only read about social media: Take a moldy campaign slogan like “safe streets,” put a hashtag in front of it, and presto—millennial bait.

“It’s obviously from social media, and it means I support jobs,” Evans says. “And it’s something that the younger voters and others might look at and say, ‘Oh yeah, he’s connected with us because he speaks our language.’”

Hashtags aside, plastering a sign on every lamp post in the city is about as old-school as a D.C. campaign can be. But posters can’t win elections. A yard sign means someone likes a candidate (not that lawn signs vote, either), but a streetlight sign only means the candidate is looking for people to like him. That, and the campaign has a big printing budget and a monomaniacal field operator.

And what a field operator Evans has. Evans’ go-to sign guy, Scott Bishop Sr., has a weathered face and a long history in District politics, including guilty pleas relating to a signature fraud scheme that lost Williams his place on the ballot in his 2002 re-election campaign. Bishop has been able to put Evans’ name on what seems like every intersection in town in just a few months because he has a system—lean the ladder against the post, wrap two posters. Then, swaddle them together with so much tape that they become as much as part of the lamppost as the bolts holding it to the sidewalk. He does all this, he says, while making sure that the signs are too high for rivals to rip down.

The first time I meet Bishop, media savvy after years of campaign work, he gives me a fake name. Later, more in the mood to tell me who he is, Bishop explains his field strategy in military terms that leave no room for hashtags. First, he pummels the neighborhood into submission with signs—that’s his “air force.” Then, he sends in the canvassers—his ground forces—to accept surrender, or in Evans’ case, their votes.

There’s something else familiar about this campaign, too: Evans’ still-burning ambition to be mayor.

“I think Jack has wanted to be mayor probably since he was an ANC commissioner in Dupont Circle,” says Ambrose.

Evans has even brought back his 1998 rationale for running: He can get more done from the mayoral suite than in Ward 2 office. “The mayor really sets the priorities for the city,” he says.

Seven years after he pulled just 10 percent of the votes in 1998, he tried again in 2005. Williams’ second term was ending, and Evans formed an exploratory committee to consider whether District residents wanted to give him another shot in the following year’s primary. The committee spent $50,000 on a poll by Democratic pollster Diane Feldman.

The results weren’t pretty. Evans pulled a few points above or below that same 10 percent he got in 1998, according to the Post. Had nothing changed? Eight years later, Evans blames his poor showing in the 2005 poll on the popularity of then-Ward 4 Councilmember Adrian Fenty, who went on to win.

So Evans dropped his mayoral ambitions for the time being and entered the race for Council chairman—only to drop out of that a few months later, too.

Apparently, he still trusts Feldman’s polling—Evans’ campaign paid Feldman’s company $48,700 for polling and mail work in the last reporting period. As for the results of that new poll, Evans says “everybody’s all bunched up,” but that it shows he can win.

Downtown nightclub Park at Fourteenth frequently hosts basketball stars like LeBron James and Dwyane Wade. In a few days, Chris Brown will be arrested nearby after partying here. But on a Wednesday night in late October, the club belongs to Jack Evans.

Evans might seem like an odd candidate to hold a fundraiser at a nightclub, but with the place decked out in Evans signs and a Halloween-themed birthday cake for his upcoming 60th, it almost starts to make sense. Besides, unlike those other celebrities, Evans has credibility not even bottle service can bring—owner Marc Barnes is a campaign contributor.

An announcer comes over the speakers: “Could everyone come to the main room for a speech? It would make the candidate very happy.”

Evans’ party is as random as more than two decades in two District politics could make it. It includes college friends of Evans’ young staffers, longtime District government workers, and Jauhar Abraham, the co-founder of anti-gang violence group Peaceoholics. And, this being Evans, there are lots of rich guys in suits who can hit the $2,000 max—and maybe, if Evans is lucky, have their corporations contribute, too. The Evans fellows manning laptops set to the campaign’s fundraising page are happy to help.

Evans has never been at a loss for campaign cash. His first mayoral run coincided, serendipitously, with an increase on the maximum legal donation to would-be mayors, from $100 to $2,000. Evans’ only opponent in his 2012 Council re-election race dropped out almost as soon as it began, alleging that a shadowy, cigar-smoking man working for Evans had been hanging around outside her house. Evans went on to raise $370,101.64 and spend $335,305.52 anyway.

That good fortune has held. Evans outpaced rivals Tommy Wells and Muriel Bowser in the August to October reporting period, raking in the $2,000 max contributions. As of Oct. 10, the last filing deadline, Evans’ campaign had taken in $767,964.25. His Patton Boggs job is worth more than the nearly $200,000 salary it brings, too—Evans’ co-workers have donated $9,750 to his campaign so far.

Even still, Evans ended the period behind Bowser in cash on hand, thanks in part to expenses like his campaign office on trendy 14th Street. But Evans isn’t deterred by the hits to his campaign’s accounts. Outside the club, an exhilarated Evans asks me a question: What are the other candidates even doing?

As a sitting councilmember, Evans can’t campaign all the time (though with a third of the Council running for mayor, it’s getting to be hard to tell the difference between campaigning and governing). So on the first Tuesday in November, Evans finds himself at the Council breakfast meeting, looking like he doesn’t want to be there at all.

“Can we have order, please?” Council Chairman Phil Mendelson asks Evans, who’d been small-talking over Mendelson’s attempt to start the agenda. “As the senior member of the Council, can we have order, please?”

Evans relents, just for a second. Soon, he’s back to his side conversations, and it’s freshman Kenyan McDuffie’s turn to be irritated. In as stern a tone as the button-downed McDuffie gets, he asks Evans to shut the hell up. “It’s amazing that the person with the most tenure on this Council is the rudest,” McDuffie says to the councilmembers in general, not looking at Evans.

The feeling’s mutual. In 2011, with the Council chaired by Kwame Brown, Evans declared that he never served on a worse one. Indictments and special elections have changed the cast some, but Evans’ mood still alternates mostly between bored and frustrated with his branch of government. (Evans says the Council has improved after the indictment-prompted exits of Brown and Harry Thomas Jr.)

He’s become a reliable foil for Mendelson, spoiling the chairman’s attempts to move the unusually early 2014 primary from April to June and successfully stomping over Mendelson’s opposition to his own attempts to delay the attorney general election four years.

I catch Evans at the elevator after another one of his procedural tussles with Mendelson, which lately arise from Evans wanting more time to talk. The chairman, Evans says, is driving him crazy. Their bickering from the dais over procedural issues is reminiscent of the Muppet Show balcony guys, but not as funny: Statler and Waldorf, after all, weren’t trying to run a city government.

Here’s Mendelson and Evans talking about the attorney general delay in October.

Mendelson: “I’m afraid your time is up.”

Evans: “Oh, Mr. Mendelson, don’t pull that. You cut me right off.”

Still, grumpy or not, Evans has a lot to tout in campaign speeches after more than two decades on the Council. He backed the Walter E. Washington Convention Center, despite those boos in 1998, and, famously, Nationals Park. When business booms in the District, as it is now, Evans can claim that he was there in the bad days.

And he’d like to keep things going with the ongoing review of the city’s tax code. A potential target: the corporate tax rate, which Evans says is keeping businesses out.

But don’t call him just the business candidate—I tried as much and got rebuked. “There’s a huge other picture out there that people forget,” Evans says. That picture includes Evans’ support for expanded arts funding, which has earned him the fundraising help of a group calling themselves “Artists for Evans.”

Then there’s Evans on gay rights—soon after he joined the Council, he helped create domestic partnership laws and repeal the city’s anti-sodomy statute. Evans says that’s inspired people to call him “the first gay councilmember,” in the same sense that Bill Clinton was “the first black president.” (Which is to say, only in the metaphorical sense; the current Council has two openly gay members.)

But Evans also uses his prominence in ways that can make you wonder whether he realizes he’s running for office. He complains that new gift disclosure rules are too onerous. He worries that the newly constituted Board of Ethics and Government Accountability is, through its frequently issued advice about how to be an ethical councilmember, setting up trip wires that could blow up on him someday. Neither concern is likely to endear him to the District’s scandal-fatigued voters.

Over the summer, Evans successfully campaigned against a traffic-slowing Wisconsin Avenue NW median in Glover Park that, perhaps not coincidentally, sat on the route Evans takes between his P Street home in Georgetown and his daughters’ schools.

“Jack Evans is concerned about getting his kids back and forth to school,” one Glover Park ANC commissioner told the Georgetown Dish. Evans insists that he was just using his own route as an example.

Still, sitting on the Council means Evans can try to win new constituencies with his votes. Evans was one of three councilmembers not named Marion Barry who opposed recommending that Barry lose his committee for taking $6,800 in cash “gifts” from city contractors. Evans says he opposed the punishment because Barry had already been fined by the ethics board. It can’t hurt in Ward 8, though, that Evans didn’t vote to punish Barry when mayoral rivals Wells and Bowser did—15-year-old comments about Barry’s “horrible” record notwithstanding.

Evans’ vote in favor of the Large Retailer Accountability Act (otherwise known as the Walmart bill) was just as counterintuitive. What was the best friend big business has in the Wilson Building doing voting for a minimum wage hike, at least for some workers?

But Evans has been splitting constituencies throughout his career. The first time he ran for the Ward 2 seat, he made his name as the anti-development candidate. Now he raises money in $2,000 increments and pushes through property tax exemptions. Former Evans spokesman Andrew Huff says Evans is torn, too, between wanting to keep money in the treasury and expanding social programs. “It’s not a natural fit all the time, but I think he’s made it work,” Huff says.

Ex-Councilmember Bill Lightfoot, Bowser’s campaign chairman and one of the other reform-minded councilmembers elected in the early 1990s called the Young Turks, has a more cynical opinion of Evans’ vote.

“Why in the hell would Jack Evans vote on the high minimum wage for Walmart?” Lightfoot says. “He’s the guy who’s viewed as pro-business. Well, he can get away with it, because where are the businesses going to go?”

To Vince Gray, for one. While would-be outsider candidates like State Department official-turned-mayoral hopeful Reta Lewis can make vague, crowd-pleasing demands for new blood in the Wilson Building’s mayoral suite, Evans is in the unhappy position of liking Gray too much to attack him—at least for now.

Evans and Gray have been on good terms since Gray ran the Department of Human Services in the early ’90s. “I don’t think he has anything bad to say about Vince,” Huff says.

Indeed, Evans says that he’s so intertwined with the city’s recent boom during Gray’s administration that criticizing Gray would be like attacking himself.

A working relationship with the mayor is great for confirming a new chief financial officer, but when you’re running to take his job, it’s a problem. In an appearance on WAMU’s The Kojo Nnamdi Show, Evans stammered through a question about whether he could say one bad thing about Gray’s record. “I think the mayor’s done a good job,” Evans said finally. “I’m a supporter of Mayor Gray.”

If Gray gets in the race, Evans will have to decide how far that support goes.

Once again, Evans is back in Ward 7. Now it’s November, and he’s at the Benning Ridge Civic Association meeting. He’s listening to an elderly man’s saga with the Office of Tax and Revenue and Evans’ own finance committee—a litany that, judging by the look on Evans’ face, he’s heard from this man before.

Evans is doing constituent service for people who aren’t his constituents, meaning he had to give the ward’s councilmember (in this case, Yvette Alexander) the heads-up that he was coming to her territory. There’s another hassle he could dispense with if he was mayor.

Even in a city as relatively small as Washington, Evans is getting whiplash from all the different interest groups he has to meet with. He says he has to beg his staff just for one night—Sunday—when he’s not at an event. Tomorrow he’ll be doing a Q&A with Petworth activists who want to hear about “social justice.” The invite promises vegan-friendly food. But tonight, he’s hearing about school boundaries and jobs programs for seniors.

Peaceoholics co-founder Abraham, who’s been sitting in the back, stands up and tries to vouch for Evans with the mostly African-American audience. “I want to make sure people east of the river know he’s always been a friend to us,” he says. Later, he’ll tell me that he thinks that, as a white person, Evans would have to be especially attentive to African-American issues.

Until then, though, it’s back to whatever Benning Ridge wants to talk about. ANC commissioner George Browne wants to know if Evans will spare voting precinct 106 from the Board of Elections’ polling place reshuffle, which could leave senior citizens in his neighborhood walking a mile to vote. Evans jokes that he’ll try to arrange it, but on one condition: “You’ve got to all vote for me.”