As civil rights activists returned to the Lincoln Memorial on a Saturday in late August to commemorate the 50th anniversary of the March on Washington, a smaller event for statehood for the District of Columbia took place not far from the Reflecting Pool.

At that rally, held at the District’s World War I Memorial, elderly activists from the city’s Statehood Green Party mixed with 20-somethings trying to make statehood sexy. “Want a date?” one young woman’s sign read. “Make D.C. a state.”

Speakers around the memorial played go-go by the genre’s godfather, Chuck Brown. The rally’s theme song, though, was “Stand Up 4 DC,” which mashes up statehood rhetoric and elevator music to surprising success. “Home Rule was cool, but man I ain’t no fool,” the song goes. “I need control of my own destiny.”

The event drew a few hundred people, including Mayor Vince Gray and Del. Eleanor Holmes Norton, who gave a speech that included asking for her own vote in Congress. One D.C. Council staffer nearby remarked that Norton must be familiar with the speech. “She’s been giving it for 40 years,” he says.

The District’s shadow delegation also took the podium. The elected shadow senators and shadow representative are treated like congressmen by the District’s government, at least officially. In Congress, however, they get treatment just a little better than every other volunteer lobbyists.

Shadow Sens. Paul Strauss and Michael D. Brown were able to address the crowd for about 10 minutes, but when shadow Rep. Nate Bennett-Fleming reached the podium, the delegation’s time was up. The organizers, who were apparently more committed to respecting their schedule than the shadow delegation, played Bennett-Fleming off like an Oscar winner in a technical category.

There was one notable absence from the rally: the out-of-town March on Washington visitors the District wanted to win over. Organizers tried to lure marchgoers with tourist maps of D.C. peppered with paragraphs about statehood, but at the fork in the security cordon between the local rally and the official March on Washington, most opted for the latter.

In the end, the rally may have been most memorable for Ward 8 Councilmember Marion Barry seizing the microphone and insisting on his own time for a speech. After weathering organizers’ attempts to cut his mic, the mayor-for-life delivered a call-and-response list of issues that statehood would solve.

“I say jobs, say statehood,” Barry told the thinning crowd.

“Statehood!”

“Black people, stop killing each other!” Barry said.

“Statehood!”

“Mothers on welfare!” Barry said.

“Statehood!”

“Statehood, statehood, statehood,” Barry finished.

After decades of failed attempts, statehood has become—to paraphrase Homer Simpson’s description of beer—the cause of and the solution to all of the District’s problems. No money-suck program can be cut off if its existence makes the District look more like a state, and no politician can go wrong supporting it. At the same time, any theoretical budget shortfall can be solved, somehow, by the commuter tax statehood would allow the District to impose.

Despite statehood’s rhetorical prominence, though, the District invests little in lobbying, in part because of federal budget riders that forbade it until 2008. That could change this fall, with At-Large Councilmember Vincent Orange’s District of Columbia Statehood Advocacy Act of 2013. Orange’s legislation would spend more than $1.1 million on statehood, including giving the delegation their first salaries—$35,000 for each member. That doesn’t compare to Norton’s salary ($174,000), Gray’s ($200,000), or the average councilmember’s ($128,202), but it’s enough to make the shadow delegation more than a pricey hobby for its members. With the District about to put money behind the delegation, it’s time to look at how the statehood fight got to this point—and whether D.C. should spend more than a million dollars on a cause that’s spent a long time going nowhere.

District residents voted for their first shadow delegation in 1990, the culmination of an idea supported by statehood activists and the Rev. Jesse Jackson’s Rainbow Coalition. (Jackson would be one of the first two shadow senators elected.) The vote took place over the objections of several members of the D.C. Council. “We need shadow reps like we need potholes,” then-Councilmember Carol Schwartz wrote in a Washington Post op-ed.

The plan was inspired by Tennessee, which had elected its own shadow delegation in 1796 to push for statehood. The so-called Tennessee Plan had already been used successfully by Alaska and Hawaii earlier in the 20th century. Its application in the District is murkier, though, since none of the future states that successfully used it had their lack of statehood detailed in the Constitution. Still, if all went according to plan, the delegation would make itself obsolete in a few years.

Three years after the creation of the shadow delegation, though, another statehood bill died in the Senate. And starting in 1995, Newt Gingrich’s Republican-controlled House meant a total halt on statehood progress. Gingrich declared D.C. a “laboratory” for GOP ideas, appointed a Republican task force on the District, and set to work pushing tax cuts and school vouchers. John Capozzi, the shadow representative from 1995 to 1997, recalls that the most exciting time of his term came when he tried—and failed—to crash a congressional orientation to get a free laptop.

The lack of progress on statehood inspired a more incremental approach focused on gaining voting rights for Norton. The most active outfit was DC Vote, a lobbying group that some statehood activists felt was overly favored by the city government. Years of negotiating meant to convince Republicans to accept a House vote for the District in exchange for another one for conservative Utah came to nothing in 2010, even though a bill to do that passed the House. Senate Majority Leader Harry Reid allowed Republican senators—and some Democrats worried about their legislative grades from the National Rifle Association—to attach an amendment to the bill that would have taken away the District’s control over its own gun laws. Norton, pushed along by a D.C. Council resolution trashing the compromise, refused to take the deal, and it died in the Senate.

Statehood regained its position as the favored goal for the District that same year, with the failure of the voting rights bill. “That’s when statehood became part of the movement again,” says Bennett-Fleming. But the antipathy between statehood and voting rights activists is still fresh. Incoming DC Vote executive director Kimberly Perry ran afoul of statehood activists when, in a July Washington Post interview, she wouldn’t rule out retroceding the District to Maryland. Activist Anise Jenkins, a member of statehood group Free DC, calls DC Vote’s voting-rights approach “the Kibbles and Bits of democracy.”

At a Council hearing on Orange’s shadow delegation bill the same month, Charles Moreland, the first shadow representative, demanded that the Council strike language in the bill that would require the shadow delegation to list voting rights as an issue on their websites.

“For statehood supporters to be yoked with voting rights proponents would be like teaming a thoroughbred horse with a long-headed Mississippi mule,” Moreland says.

In the basement of the John A. Wilson Building, there’s a door that’s locked most of the time, even during business hours. Only one of the building’s elevators goes there. Show up at the right time, though, and you’ll find yourself in the shadow delegation’s shared office suite.

Shadow Sen. Michael D. Brown decorates his portion of the office with mementos from his time working as a political consultant for the national Democratic Party: a picture of a much-younger Brown shaking hands with Jimmy Carter on the president’s doomed 1980 campaign; a signed Doonesbury cartoon.

The rest of Brown’s office is devoted to the detritus of the statehood campaigns he’s dreamed up. There’s mock-ups of statehood billboards at the 2012 Democratic convention in Charlotte, N.C., funded by his share of voluntary donations from D.C. residents. (A piece of paper pasted under the pictures of the signs boasts that they “received a lot of press coverage.”) Brown pulls out a guide he produced for teachers who want to teach statehood in their social studies curricula. One high school class in Missouri, Brown claims, ended up haranguing their state legislators over D.C. statehood after taking the course Brown designed.

Brown is keeping busy, despite his slim budget. His office sponsors the DC Breeze, one of the District’s two professional ultimate Frisbee teams. The sponsorship cost $500, an expense which won Brown the right to hang a statehood banner at their games and to throw out the first disc of the season. And he’s on to new ideas, including statehood-branded beer and hot dogs, which he’s planning to call “Freedom Franks.” He’s working on special recipes for the most ardent opponents of statehood. Texas Rep. Louie Gohmert, a Republican who regularly introduces bills to cede the District back to Maryland, will certainly earn his own dog, according to Brown. A volunteer designer is working on a costume for “Freedom Frank,” the wieners’ mascot.

“It’s a fine line I walk, trying to engage people without being a buffoon about it,” Brown says.

Brown estimates that he’s spent $40,000 of his own money on statehood. But until recently, the shadow delegation has also drawn on the statehood tax check-off, a box on D.C. income forms that allows filers to donate money to the cause. Last year, the tax contribution earned $12,000, which was split among the three members of the delegation. Brown expects that the donation option will be cut from the tax forms entirely next year due to lack of interest.

The plan was always problematic, with the Office of Tax and Revenue forgetting in 2006 to print the box on tax forms at all. Instead, would-be residents of New Columbia had to write “STATEHOOD” at the bottom of their filing. Brown blames the decline on e-filing methods like TurboTax not featuring the contribution options. In fact, the tax form contribution is available on all forms of electronic filing, according to a spokeswoman for the Office of the Chief Financial Officer.

That may not entirely be a bad thing—in 2008, the tax money was spent on things like hosting a statehood luncheon with Hayden Panettiere. Yes, that Hayden Panettiere—the star of NBC’s Heroes-turned-whale conservation activist-turned-D.C. statehood supporter. Panettiere became interested in statehood when she met Strauss at a 2008 campaign event for Barack Obama and asked him to use his position in the Senate to protect whales. Strauss explained that he couldn’t, because he wasn’t really a senator. “If you’re out there fighting for the rights of vote-less mammals, well, I’ve got 600,000 of ’em right here in the city,” Strauss told Roll Call.

Brown’s tenure hasn’t been without some accomplishments. The shadow senators have wrested some perks from the Senate, including Senate license plates and ID badges that allow them to access the Senate dining room. (Bennett-Fleming claims that he’s been too busy fighting for statehood to investigate whether he gets any representative-like privileges on the House side. Probably not; a spokesman for House Speaker John Boehner, when asked whether Bennett-Fleming enjoyed any perks, says there’s no such thing as District shadow representative.)

Brown worries, though, that a Republican-controlled Senate could take away all the privileges, however minor. Without statehood, Brown says, he’s stuck relying on the kindness of strangers.

“I often call myself the Blanche DuBois of American politics,” he says.

Even Brown’s privileges as a quasi-senator don’t afford him much access to actual senators. Instead, he says he’s typically only able to make 20-minute appointments with staffers. His best lobbying moments have come out of happenstance—buttonholing Maryland Sen. Ben Cardin at a University of Maryland basketball game, or ending up on a love seat with then-Sen. Hillary Clinton when she was courting Democratic super-delegates like Brown and Strauss in 2008.

The stunt-based approach to statehood that Brown favors doesn’t always go so well. In 2008, Brown, along with then-Mayor Adrian Fenty and eight members of the D.C. Council, flew to New Hampshire to convince their state legislature to back a resolution scolding the Granite State’s senators for not supporting District voting rights. The bill died in the legislature, but that didn’t stop District politicians from going back to New Hampshire to support another bill last year. That failed, too.

Five years after the first trip to New Hampshire, Brown’s still stewing over the Post’s coverage, which included a description of At-Large Councilmember David Catania reading horoscopes. “They made us sound like the glee club from George Washington University that went to a party to sing,” Brown says.

Strauss, an attorney whom Brown describes as the lobbyist in their trio, has had a flashier tenure. On the glitzier side of pseudo-senatehood, he’s palled around with Panettiere, escorted a D.C. beauty queen through the halls of Congress, and staged a mock tea party at the 2004 Democratic convention in Boston by pouring tea into the harbor. Strauss is a frequent sight at District parades, walking next to a blown-up cover of the 1930’s pulp drama The Shadow.

His 16 years in office haven’t always gone so smoothly. Strauss was arrested in 2005 for arguing with police at a Georgetown dock and in 2008 for driving under the influence. (He received probation.) He prominently displayed his Senate ID badge during his DUI arrest, according to police documents—a bold move for an actual senator, even more so for someone whose Senate office is actually in the Wilson Building.

Then there are the interns. Because the shadow delegation can’t afford professional staffers, interns play an outsized role in their office. (When I meet him, Bennett-Fleming is accompanied by a two interns who double as his statehood encyclopedias.) Strauss has a reputation among statehood activists for employing foreign interns who don’t realize when they apply that he’s not a real senator. Strauss’ opponent in next year’s election, furniture magnate Pete Ross, pointedly mentions that he won’t have interns from Paris.

Strauss’ interns are as numerous as they are foreign. Strauss arrived at the 2008 Democratic convention in Denver with seven interns in tow, compared to one person in Brown’s entourage. Stranger, Strauss had them outfitted with Secret Service-style earpieces, according to convention coverage in DCist and the Post. All the coordination didn’t pay off for the District—that year’s Democratic platform, like the platforms in 2004 and 2012, didn’t mention D.C. statehood.

Strauss didn’t respond to requests for comment placed through one of those interns.

License plates and ID badges and tony lunches aside, both Strauss and Brown have tried to ditch the job. Seven years ago, Strauss ran unsuccessfully for the Ward 3 D.C. Council spot. The Washington Times, at least, wasn’t impressed with the shadow delegation’s name recognition. “As the city’s shadow senator for the press 10 years [sic], Paul Strauss is coming out of what amounts to the Witness Protection Program,” one reporter wrote.

Brown’s political career may ultimately be more damaging for the delegation’s future. In 2010, he ran against then-At-Large Councilmember Phil Mendelson in what he says was an attempt to raise more publicity for statehood. Brown says he was hoping to come in second, bringing up his pet issue in every debate.

More cynical observers figured that the white Brown—quickly nicknamed White Mike—was trying to capitalize on his name similarity with the better-known, African-American then-At-Large Councilmember Michael A. Brown. Brown’s version of the story goes like a penny-ante Macbeth, with his modest ambitions to run as a publicity stunt replaced by a hunger to win when he saw a Post poll two weeks before the Democratic primary that showed him ahead of Mendelson. It’s hard to believe this was because of residents’ love of the shadow delegation or heavy campaigning on Brown’s part: A month before the primary, Brown had raised no money. Once the poll came out, he started publishing confusing flyers without his face or mention of his shadow senator work. In return, people scrawled “White Man” on his signs in Ward 8.

“In the end, I did a lot of harm to myself,” says Brown. That includes potentially earning the enmity of Mendelson, who, as Council chairman now, has a lot of say about the future of the delegation funding bill.

At least Brown’s trying to make nice—city gift disclosures show that he treated Mendelson to lunch at McCormick & Schmick’s in July. Before the shadow delegation can lobby Congress, apparently, it has to lobby its own government.

At just 28 years old, Shadow Rep. Nate Bennett-Fleming doesn’t bring the same political baggage as his Senate counterparts. But that doesn’t stop him from possessing the defining characteristic of statehood activists, namely, distaste for other statehood activists. He rattles off the problems with the statehood movement before he joined: “disjointed,” “ad hoc,” not “strategically sound.”

“Our movement is laughable almost,” says Bennett-Fleming. Why Bennett-Fleming, a Berkeley Law School graduate and an adjunct professor at the University of the District of Columbia, would sign on with such a joke of a movement is one of the curiosities of the statehood delegation. For his part, Bennett-Fleming says that he doesn’t have ambitions for any higher office of the sort that people outside the District actually recognize.

While Brown thinks of promotional schemes and Strauss hosts parties, Bennett-Fleming and a crew of D.C. university students who work as his interns focus on meetings with congressional staffers. They point to a statehood bill introduced by then-Sen. Joe Lieberman late last year, just before he retired. (It didn’t pass.) In June, at a ceremony adding a statue of Frederick Douglass as the District’s addition to the Capitol’s Statuary Hall, Senate Majority Leader Reid reiterated his support for statehood. That support, though, seems mostly symbolic: So far, it hasn’t convinced Reid to make D.C. statehood a legislative priority or advance a bill for it through the Senate.

Bennett-Fleming and his entourage focused their lobbying on minority caucuses like the Congressional Black Caucus and the Congressional Asian Pacific American Caucus, rounding up 50 co-sponsors for the House’s statehood legislation. Bennett-Fleming says this is a sign the statehood movement is back from past defeats, but that’s only a little more than a tenth of the body’s members. For all their work, statehood supporters are basically just winning over Democrats in a chamber controlled by Republicans.

And Republicans really, really don’t want to make D.C. a state. Putting aside constitutional issues, it’s hard to imagine the GOP welcoming two senators from a city where winning the Democratic primary practically guarantees electoral victory.

“We’re too black, we’re too urban,” says Brown, paraphrasing Ted Kennedy’s explanation of why D.C. will never receive a real congressional delegation. “We’re too Democratic, and we’re too liberal.”

Those doubts hint at a truth that goes unmentioned at rallies and Council hearings, a truth that $1 million or $10 million from the District’s budget won’t solve. Statehood isn’t foundering because the rest of the country doesn’t care (although that’s true). It’s been stalled for decades because Republicans don’t want to empower a guaranteed vote for Democrats.

The failure to get at that fundamental problem—and the hopeless situation it creates for the District—leaves activists jumping between whole-hog endeavors like statehood and more incremental demands like budget autonomy or voting rights. The logic behind pushing for statehood above all else makes perverse sense: If we’re not going to get anything, we might as well try for as big a portion of nothing as possible.

But the shadow delegation’s description of how it would use the proposed budget, which includes $75,000 for each of them to hire staffers and $75,000 each for promoting statehood, doesn’t inspire much confidence. Mendelson asked Strauss at the hearing on the bill why he hadn’t brought his own speculative budget, but Strauss demurred. Since the shadow senators and representative are elected just like councilmembers, according to Strauss’ logic, the delegation shouldn’t have to justify how it will spend money from the Council. “When money is given to other elected officials, there’s some deference to those agencies,” Strauss said.

Without the ability to change the make-up of Congress, the shadow delegation’s remaining goal—keeping the demands for statehood at a low hum—doesn’t require much money at all. Joshua Burch, a Brookland resident who’s mentioned by Capozzi as one of statehood’s best hopes, leads lobbying trips of District residents to the Hill. Burch’s success without District money demonstrates the one advantage the District’s statehood push does have: the people who want it live next to Congress.

Orange, who introduced the bill, didn’t respond to a request for comment about the bill through his staff. The bill, which includes another $550,000 for the Council to spend on statehood-related lobbying and advertising, stands a good chance of passing the legislature. It’s already been co-sponsored or co-introduced by five other members.

Bennett-Fleming bristles when it’s pointed out that, co-sponsors aside, the statehood bills will likely never become reality as long as Republicans control half of Congress. And that’s generous—even when Democrats controlled the presidency and both the House and the Senate, the District wasn’t even able to get a favorable voting rights bill passed.

“It doesn’t take a genius to see the bill isn’t going to get passed,” says Bennett-Fleming. Instead, the repeated requests for co-sponsors every congressional session is meant to get members used to supporting statehood. No matter how well members of Congress are drilled to support statehood, though, that doesn’t translate into progress until votes are actually taken on the legislation.

One possibility popular with activists for getting around Republican opposition is teaming up with Puerto Rico as a two-state package. The party’s 2012 convention platform supported statehood for the island, this thinking goes, so why not throw D.C. in, too? Under this theory, Republicans would allow the deal in an attempt to win back Hispanic voters scared off by the party’s vacillation on immigration reform. “You would think that the national Republican Party would do everything it could to stop the fastest-growing minority in the United States from becoming a sure thing for the Democratic Party,” local TV analyst and statehood gadfly Mark Plotkin wrote in a 2012 op-ed in the Post.

There are several problems with teaming up with Puerto Rico, including whether the Republican leadership could corral its members to support the statehood package and whether two Democratic senators from the District for two Puerto Rican senators with party affiliations to be named later would really amount to an even trade. Supporters of the two-for-one statehood deal also ignore something else: Puerto Rico doesn’t want us.

Puerto Rico Resident Commissioner Pedro Pierluisi—essentially the territory’s equivalent of Norton—thinks the District should find another partner. “We’re talking about different quests,” he says.

While statehood may be decades away, the Council will consider the funding bill this fall. For Brown, at least, time is running out. With two children in college and another soon to follow, he says he needs to starting getting paid for his lobbying from Orange’s bill, or he’ll have to quit. Whether that would be a bad thing, of course, depends on your opinion about the efficacy of novelty hot dogs and brief meetings with Senate staffers.

Facing the end of his statehood career, Brown expresses a sentiment more common among failing artists than congressional lobbyists with Senate IDs: It sucks to have a job you love and not get paid for it.

For Bennett-Fleming, the potential funding boost offers another opportunity: rehabbing the shadow delegation’s reputation in the District. “Clearly, the shadow delegation isn’t held in the highest esteem of the voters,” he says. Will we love them more once they get six figures of taxpayer money to spend?

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