There’s something about Andy Shallal that inspires art. Since launching his mayoral bid in November, he’s already been painted three times, once in a tableau with Lethal Weapon star Danny Glover.

Last week in a living room in tony Cathedral Heights, it’s “Puff the Magic Dragon” songwriter Peter Yarrow’s turn to have Shallal as his muse.

“This light in Andy’s heart,” Yarrow sings, to the tune of “This Little Light of Mine.” “I’m going to let it shine.”

Yarrow, the Peter of ’60s folk group Peter, Paul and Mary, sees Shallal as a little bit Martin Luther King Jr., a little bit failed Vietnam War–era presidential candidate Eugene McCarthy. There are other spirits about tonight, too—Yarrow claims that the essence of recently deceased singer Pete Seeger is with us, then asks the crowd to hum the tune of Seeger’s “Where Have All the Flowers Gone?” along with him and Shallal.

When it’s Shallal’s turn to speak, though, he opts for words all his own. It’s time to drop the line that connects an Upper Northwest living room tastefully decorated with abstract art to the homeless on Anacostia’s Good Hope Road SE, where Shallal’s opened a campaign office. It’s one he uses a lot, something to explain away the contradictions inherent in the owner of the ubiquitous Busboy and Poets chain pitching himself as the friend of the common man—a paradox rival Muriel Bowser sums up as “a rich socialist.”

“More and more, I have become uncomfortable with my comfort,” Shallal says, to finger-snaps. (This is a finger-snap crowd.)

Here’s the D.C. outsider candidate, circa 2014: A 6-foot-3 Iraqi-born restaurateur as anxious about race and class as the people he seeks to represent. While his rivals opt for blue or red power ties, Shallal’s look like they were cut from one of Marion Barry’s more outré dashikis of decades past. Some of his policy ideas—lowering the voting age to 17, then turning the senior year of high school into a civics year for students to agitate; dedicating 1 percent of city agency budgets to art—sound like they were hatched during the occupation of a university administration building.

Though he’s not much of a factor in the polls so far, Shallal’s built an army of celebrity endorsers— journalist Barbara Ehrenreich, noir writer George Pelecanos, former Black Panther associate and longtime activist and academic Angela Davis. Tired of fielding questions about his policy ideas at debates, he craves hypotheticals that would test his character. Maybe the moderator could pose a scenario about how he’d handle a crisis.

If Shallal’s not a typical candidate, he’s taken to the work like one. Passing off restaurant management to his brother and daughter, he stands outside elementary schools in freezing weather, sliding over ice to hand his literature to school bus drivers. That campaigning, Shallal claims, has restored his own faith in humanity.

“I would recommend running for office,” Shallal tells the crowd in Cathedral Heights, making his bid sound like a spa weekend.

Shallal is holding court in the Langston room (named after poet Langston Hughes, naturally) of his 14th Street NW Busboys and Poets when a tourist interrupts him. She wants to see the collage mural of social justice icons that encircles the room, made by Shallal himself.

“Would you vote for me if you were here?” he asks her.

By the time she’s done looking at the mural, she’ll cut a check for Shallal’s campaign. Running a campaign and a restaurant at the same time can have advantages.

At political events, Shallal brandishes his restaurants like other candidates use their legislative records. The D.C. Council passed paid sick leave for restaurant workers? Shallal already gives Busboys and Poets employees sick time. Unemployment’s at a five-year low under Gray? Shallal claims he’s created 530 jobs himself.

He didn’t initially intend to be in the restaurant business. After graduating from Catholic University in 1975, Shallal launched a short-lived attempt at a medical degree at Howard University. Then he headed to San Francisco, choosing the city because, he says, it was the farthest he could get from the East Coast. In 1981, he came back to D.C. and fell into waiting tables at the Foggy Bottom Cafe, proving adept enough at it to rise to the rank of manager. Along the way, he had two sons with his first wife, and two daughters with his second.

In 1987, Shallal opened Skewers, the first of many restaurants he would start, in Dupont Circle. Using other floors of the rowhouse, he followed up with another restaurant, Cafe Luna, then a bookstore, Luna Books and Democracy Center. (He sold both restaurants in 1996.)

With the help of a donated library from future presidential spoiler Ralph Nader, whose office is nearby, the bookstore became a hotbed for liberal activists, from Zinn to staffers on once-and-future California governor Jerry Brown’s 1992 presidential primary bid against Bill Clinton.

“It was the coolest little spot,” Shallal says.

But one floor of a Dupont Circle rowhouse wasn’t a large enough stage for Shallal’s politics. Wanting to make the combination restaurant-bookstore more accessible, he took out a $2.5 million loan to buy the space that would become Busboys and Poets at 14th and V streets NW in 2005. It’d go on to be Shallal’s most successful restaurant, with four locations in the D.C. area and two more planned. (Opening a Busboys east of the Anacostia River, a much-discussed goal of Shallal’s, remains out of reach for now due to what Shallal calls the “complicated” nature of the deal.)

The business’s name comes from Hughes’ stint as a restaurant busboy. The Hughes homage comes naturally to Shallal—it’s a rare public appearance where Shallal doesn’t quote from Hughes’ “A Dream Deferred.”

But not everyone’s comfortable with the idea of a restaurateur profiting from Hughes’ legacy. In 2011, a poet, disgruntled over the pay for performances at the restaurant and a sense that Shallal was commodifying African-American culture, stole a cardboard cut-out of Hughes from the 14th Street Busboys. The theft and an ensuing open letter to Shallal from District poets sparked a debate about what Hughes would have thought of his role in the restaurant. The spat inspired Shallal to double the pay for poets, from $50 to $100.

The so-called “Flat Langston” fight aside, though, Busboys these days comes off like one of the least problematic parts of the remade neighborhood. Part of that is how long the restaurant’s been around—on booming 14th Street, where a new apartment building is somehow themed around both Louis Armstrong and France’s Louis XIV, nine years in one place can seem like a century.

“They come here, they don’t see places like this,” he says, as another group of customers asks to see the mural.

Shallal started considering running for office last year, while the ongoing federal investigation into Mayor Vince Gray’s 2010 campaign left the city looking for an outsider candidate. Maybe the District was on the brink of repeating its 1998 election, where bow-tied accountant Anthony Williams swept aside both the city’s fiscal ruin and the bickering councilmembers-turned-mayoral hopefuls who had been complicit in it. Unluckily for residents hoping for someone new, though, none of the so-crazy-they-just-might-work nominees political consultants whispered to each other about—U.S. Attorney Ron Machen, police chief Cathy Lanier, Williams-era city administrator Robert Bobb, and even Williams himself—were interested.

While the rest of D.C. was looking for a white knight, though, Shallal was looking at Gray—and he didn’t like what he saw anymore. He’d backed Gray over ex-Mayor Adrian Fenty in 2010, though he’d given $1,000 to Fenty’s re-election campaign almost two years earlier; by the time anyone actually started voting, Shallal says, he’d become convinced the city needed someone new.

Three years later, Shallal felt like it was Gray’s time to go, too. Shallal says he was disappointed not to have a larger voice in Gray’s administration. “I really didn’t feel that there was a receptive ear there, honestly,” Shallal says.

Late last summer, Shallal met with Gray to try to persuade him not to veto the Large Retailer Accountability Act, which would have mandated $12.50 minimum wages at certain big-box retailers (read: Walmart). His intervention proved unsuccessful—Gray blocked it anyway, after Walmart threatened to kill at least three of its planned stores if the legislation became law.

For Shallal, it represented everything he’d come to dislike about Gray’s administration.

He’d toyed with the idea of running for office before, but he thought now was his time. It wouldn’t be his first foray into District politics. While he’d focused much of his activism on heady global issues like peace between Israel and Palestine, Shallal worked on a successful 1992 initiative to limit individual donations to District candidates to a $100 maximum. The limits were eventually revised upward to $2,000, and Shallal jokes with donors now that they shouldn’t hold themselves to the now-defunct $100 limit.

Shallal’s made several donations of his own to District candidates, from $1,000 to Ward 1 Councilmember Jim Graham’s 2010 re-election to $250 for future mayoral rival Muriel Bowser’s 2008 campaign in Ward 4.

His most recent involvement in District politics—chairing the 2012 re-election bid of At-Large Councilmember Michael Brown—didn’t exactly bode well for his own ambitions. Brown lost the race after $114,000 disappeared from his campaign bank account, then went on to plead guilty for taking bribes from the FBI last year. (Shallal says he was “disgusted” when he heard about Brown’s crimes.)

Last fall, as he considered running, boxing promoter-turned-District gadfly Rock Newman emailed him a lengthy memo talking up his chances. Shallal was untainted by ethics scandals, Newman wrote, and he was rich enough already that he could reassure voters that he wouldn’t go on the take himself.

Shallal started to inch closer to an announcement. Still publicly supportive of Gray, he told reporters that he was considering running, but only if Gray didn’t. He launched an exploratory committee. He said he could even see himself dropping out of the race if Gray decided to seek another term.

The early January deadline for picking up petitions got closer, and Gray remained ambivalent about his plans. A few weeks after opening his exploratory committee, Shallal admitted that he would pick up the petitions required to make the Democratic primary ballot when they were available, but wouldn’t necessarily run for mayor—a head-scratcher of an explanation that didn’t conceal his intentions.

Finally, in November, Shallal declared he was going to run for mayor no matter what Gray did. When Gray entered the race a month later, Shallal stayed in, and went on to become one of the incumbent’s most persistent critics.

By the time he kicked off his campaign on Nov. 12, Shallal had figured out a way to describe himself beyond “Vince Gray with a restaurant.” He slammed Gray’s “One City” slogan as too paltry for a city as complex as D.C., although he concedes that it once “sounded very good” to him.

The city’s economy could be booming, symbolized by the rising number of cranes that Gray likes to mention in speeches, but cranes weren’t enough. “We can’t just continue to count cranes,” Shallal said. “We have to count the things that really count, the things that matter.”

Newman, now chairing Shallal’s campaign, plays up the outsider angle he sold Shallal on to get him into the race, introducing him at the event as “someone wholly untainted by the cesspool of Washington, D.C., politics.”

If Shallal’s untainted by the District’s scandals, though, he’s far from untouched by the District’s other woes. In speeches, Shallal is ambivalent about the city’s changes. His restaurant empire has given Shallal a net worth that he estimates is somewhere between $12 million and $15 million—including an Adams Morgan rowhouse valued at more than $1.5 million. He’s wealthy enough to contribute or loan $100,000 of his own money to his campaign so far, making up nearly half of the $224,024.38 he’s raised.

At a candidates’ forum hosted by the Ward 8 Democrats, though, Shallal showed himself to be conflicted about the changes his restaurant and those like it had wrought around 14th Street. While he praised “the most gentrified area in the entire city” for its businesses, Shallal warned the crowd to reject that style of gentrification in their own neighborhoods.

“If that’s what the development looks like in the city, beware,” Shallal said.

And Shallal isn’t the only commentator taking a look at the midcity boom with mixed feelings. In 2012, a Washington Post writer listed Shallal’s Busboys and Poets on a list of U Street area restaurants he accused of “swagger-jacking” because they were “based on some facet of black history, some memory of blackness that feels artificially done and palatable.”

More recently, anti-violence activist Ron Moten—a vocal opponent of Gray’s for the last four years—paid Shallal a clumsy compliment at an event, telling African-American audience members they couldn’t be mad at Shallal for monetizing their history since they hadn’t done it themselves.

As for the irony of the owner of Busboys and Poets decrying the downsides of gentrification, Shallal doesn’t see it. “It’s unfair to really blame individuals or businesses for gentrification,” he says.

Ignore the other big differences between Shallal and the last successful “outside” mayoral candidate, Williams—the fact that Williams was intimately familiar with the District’s finances after serving as the city’s chief financial officer, while Shallal’s mostly stayed away from the Wilson Building—and a more fundamental one remains. Where Williams, a Los Angeles native, came from outside the city’s political world and culture initially, Shallal and his contradictions—complicity in upscale redevelopments, and the ensuing discomfort with his comfort—are distinctly of it. Dry, book-balancing Williams was disconnected enough from the city to solve its fiscal crisis. Shallal is, if anything, all too familiar with the new local crisis of the moment: what an increasingly white, increasingly wealthy city does for those who are neither.

“It’s really like the outsider rides in on his white horse,” one potential donor at the Yarrow fundraiser tells me.

I hope she didn’t say the same to Shallal. When I ask Shallal what he thinks of playing the hero in the “white knight” narrative, Shallal reacts like I’ve dropped a racial slur. The “white” part of white knight is the problem. He tells me to be more careful with my words.

In January, the Shallal celebrity roadshow puts in another performance, this time with Danny Glover—the campaign’s “lethal weapon,” per Shallal—in tow. At Anacostia’s Union Temple Baptist Church, Shallal, Glover, and golden robe–bedecked pastor Willie Wilson take in the mostly African-American audience’s grievances.

Activist and sometime Council candidate A.J. Cooper warms up the crowd, calling out a list of politicians—Vince Gray, Michael Brown, At-Large Councilmember Vincent Orange (another one of the five members out of 13 who are either running for mayor in the Democratic primary or contemplating an independent bid in the fall)—who have let them down.

When Shallal takes the mic, he paints a picture of the District’s haves and have nots. Shallal’s so fond of the “tale of two cities” metaphor, so successful in New York Mayor Bill de Blasio’s campaign, that he jokes about carrying a copy of the Charles Dickens book with him.

“They’ve been left in the shadows of those cranes, in the shadows of those high rises,” Shallal says of the people left behind the District’s boom. “They’ve become invisible.”

Shallal goes on, pitching himself as the only candidate willing to talk about the “race overlay and underlay” to everything going on in the District. The closing of neighborhood schools, standardized testing in the ones that remain open, the District’s underfunded office for rehabilitating ex-offenders, the police presence east of the river—there’s a racial aspect to it all, and Shallal will make that clear as mayor, he promises.

“We’re far from being post-racial,” Shallal says. Shallal offers himself as not just an outsider to the Wilson Building, but an outsider to what he says is a citywide consensus not to talk about race.

Being willing to talk about race at Union Temple Baptist, of course, is like bravely promoting the Atkins Diet at Outback Steakhouse. Wilson made headlines in the ’80s for threatening to roll an Asian-American shopkeeper’s head down the street. Last December, Wilson’s church played host to an “emergency” meeting on gentrification organized by outspoken anti-Semite and former New Black Panther boss Malik Zulu Shabazz. A Nation of Islam representative on the panel warned white members of the audience not to race-mix. (Shallal appeared too, with much less incendiary remarks.)

Shallal’s own ethnicity—he was born Anas Shallal in Baghdad in 1955, with the name Andy sticking after he came to the United States at age 10—puts him outside the black-white dynamic so central to District politics. He’s not white, so he doesn’t quite set off “first white mayor” alarm bells. He’s outside that spectrum, theoretically making him able to see the city’s racial dynamic from the outside.

“If I was white and I came to this country, I probably wouldn’t notice it,” Shallal says.

Shallal likes to tell a story about moving to Arlington as a kid in the 1960s, trailing his father, an ambassador for the Arab League. Shallal’s race presented a conundrum for the students at his new school, used to classifying each other in a white-black dichotomy, especially with the backdrop of the civil rights movement. He was too dark-skinned to be white, not dark-skinned enough to be African-American. Maybe, they decided, he was “high yellow”—a person of mixed ancestry.

In Shallal’s racial awareness origin story, that awkward beginning segues into the horror of King’s assassination and the riots to follow. Race, Shallal realizes, was not the joke he had thought it was.

After Shallal wins just 13 out of 307 votes in a Ward 8 straw poll in late January, an activist in the ward warns me that suspicion of Shallal’s ethnicity will doom him there. People she knows are unhappy enough about the prospect of a white mayor. They definitely won’t trust an Iraqi one in the city’s top job.

When I bring it up with Shallal, he tucks it into his narrative. People in Ward 8 don’t trust people in Ward 1, and vice versa. None of them trust politicians, regardless of race, he says.

“I don’t blame people for not trusting anybody, frankly,” Shallal says.

Running an offbeat campaign has its downsides. Polls show Shallal with rock-bottom name recognition, no matter how popular his restaurant chain is, and he’s struggled to win over the deep-pocketed developers whose LLCs are backing various councilmembers’ campaigns. (Unlike Ward 6’s Tommy Wells, Shallal’s rival for the “progressive” vote, Shallal accepts corporate contributions.) Even with Newman’s backing, the boxing promoter’s pal Marion Barry thinks so little of Shallal’s chances that he won’t even meet him for lunch.

In November, Shallal called Keith Carbone, a veteran of District political campaigns for the likes of Jack Evans and Vincent Orange. In Carbone’s telling, Shallal wanted him to leave New York City and come back to D.C. and manage his campaign’s field operations.

The campaign had early signs of trouble, according to Carbone. When Carbone tried to talk to reporters he knew from previous campaigns, he claims, other staffers told him to stay away from the media. After a boisterous kick-off at Ben’s Chili Bowl (the bongo drummers alone cost $400), Shallal’s organization collected the names of many enthusiastic volunteers, then struggled to get any of them to help gather signatures. Turning dissatisfaction with the District’s government into volunteers was proving harder than Carbone expected.

Still, he had high hopes in the first days of Shallal’s run. He remembers leaving Busboys and Poets after a campaign meeting and hearing two passers-by talk about his boss. One of the men asked who Shallal was.

“Are you kidding?” said the other. “He’s going to be our next mayor.”

Carbone was the rare District political insider on Shallal’s staff. Instead of filling his payroll with the small pool of political hands familiar with District elections, Shallal chose operatives as outside of previous city contests as he is. Both campaign manager Bob Muehlenkamp and campaign spokesman Dwight Kirk come from organized labor.

“It was like something out of a movie, where the outsider thinks that he’s going to be able to run a completely unorthodox campaign and show everybody,” Carbone says.

Carbone never got a chance to find out what that would translate into in the field. A few days after he started, other staffers started to treat him like a potential double agent, using his past work for Orange and Evans as evidence of disloyalty. Shortly after that, Carbone says, the campaign rescinded his job offer. His exit even earned Carbone a notice on the campaign’s website, in a statement describing him as “not appropriate for helping to build a grassroots movement in Washington to change business as usual.”

At fundraisers, Shallal will give his stump speech—boo cranes, yay being uncomfortable with being comfortable. Then the hard job falls to Muehlenkamp, who has to convince the crowd that the good feelings generated by an appearance from Yarrow or Glover are worth giving money to a guy who has enough money to fund much of the campaign on his own and is lingering at the bottom of the few polls released publicly so far, to boot.

The argument, billed as a glimpse into campaign strategy, boils down to people liking Shallal when they know he exists. If only he had more cash, Muehlenkamp says, he could reach more people. Reaching for your checkbook yet?

Shallal’s prospects hang over every event he does. Early polling suggests those chances are slim. A Washington Post poll from January showed Shallal receiving only 5 percent of the vote citywide, putting him behind every candidate except former Clintonite Reta Lewis and White House party crasher-turned-rapper Carlos Allen. Gray, Shallal’s one-time chosen candidate, led the field with five times Shallal’s support.

Worse, despite lavishing attention on Wards 7 and 8, Shallal received 0 percent of the prospective vote there in the Post poll. Muehlenkamp says a poll commissioned by the campaign around the same time produced similar results.

Maybe the District isn’t as interested in an outsider candidate as Shallal thought, suspicions that Shallal’s bid is just a vanity run will prove correct, and his only new responsibility next January will be making another mural for his restaurants. The District’s political consultants and sign-printers will be at least $100,000 richer, and the folk-singer-revival model of fundraising will be gone forever.

Or not. Maybe, as Shallal hopes, his run—win or lose—will get people talking about race and class in a city that’s reluctant to do that.

“If we continue to think of ourselves as color-blind, then I think we’re always going to be tripping over ourselves,” Shallal says.