When construction workers beginning the renovation of Theodore Roosevelt Senior High School last fall removed the ceiling in the cafeteria, they found a surprise. The newly exposed top of the wall revealed part of a mural, spared the five layers of yellow paint that had been applied to the rest of the wall over the decades. A muscle-bound trapeze artist hurtled into the air while Mickey Mouse looked on gleefully. Two men surveyed a parcel of land, while a Paul Bunyanesque lumberjack laid down his axe. A cowboy on horseback galloped along, guns blazing.

Photographs by Darrow Montgomery

Together with restoration experts, the team uncovered more of the mural. Their discovery, it turned out, was a 1934 New Deal–funded fresco by a 26-year-old artist named Nelson Rosenberg, who called his work “The American Panorama.” The glorified workmen and athletes who had once beheld the Roosevelt Rough Riders eating their lunches had been covered up and then completely forgotten over the next 80 years.

The construction team is restoring the mural, which spans two walls of the cafeteria, and may move it to the school’s entrance to give it greater prominence. It’s a fraction of the work that’s being done to restore Roosevelt to its former glory. The $127 million, two-year school modernization aims to revive and elevate the 1932 Colonial Revival building, “a building that has great DNA,” says lead architect Sean O’Donnell of Perkins Eastman, but that’s fallen into disrepair. The elegant front entrance, with its grand staircase and ring of columns, has long been blocked off by plywood, forcing students to snake their way through a narrow parking lot to the back door. The stately brick facade, topped with a proud white steeple gazing down on 13th Street NW, is marred by flaking paint, forbidding grates on the windows, and graffiti. Inside, water damage is everywhere, hallways are dark, and many of the windows in the classrooms fortunate enough to have them are cracked.

The new Roosevelt will be a palace by comparison. The front entrance will be restored; flanking it will be two more columned entrances to the arts and athletics wings of the school. The claustrophobic central courtyard will become a spacious, glass-topped atrium, and two new courtyards will be added to bring light into the building’s dark, 1970s-era additions.

But the glamorous new building will be mostly empty. The old Roosevelt had a capacity of 1,059 students; the renovated version will hold about the same. Last year, 473 students attended the school, and the projected enrollment for this year was just 446. That’s the lowest enrollment of any of the District’s nine neighborhood high schools.

Part of the problem is the school’s poor track record, reflected in dismal test scores, that may be scaring off potential students. Last year, more test-takers at Roosevelt scored “below basic” in math on the District of Columbia Comprehensive Assessment System exam than at any other D.C. Public Schools neighborhood high school—45 percent, to fewer than 20 percent who scored “proficient.” In math and reading growth, which compare students’ progress to that of peers who started at the same achievement level, Roosevelt likewise comes in dead last. Fewer than half of entering Roosevelt 9th-graders graduate in four years.

Roosevelt’s declining enrollment comes as its surrounding Petworth neighborhood is on the rise. Once poor and crime-ridden, the area around Roosevelt is at the epicenter of D.C.’s gentrification wave. Luxury apartment buildings and upscale restaurants have sprung up around the Georgia Avenue Metro station. Last year, the Washington Business Journal labeled Petworth “D.C.’s Hottest Housing Neighborhood” for its 42 percent jump in housing prices from the year before.

The Petworth boom comes with its own problems; low-income families are starting to find themselves priced out of their longtime neighborhood. But it’s also brought a large number of educated middle-class professionals, often with young children. In theory, these families would someday send their kids to Roosevelt, which would boost enrollment, bring socioeconomic diversity to the school, and help mitigate some of the problems that tend to be associated with high-poverty student bodies.

In theory.

In reality, few of these children are likely to attend Roosevelt. Historically, families of means moved out of the District or sent their kids to private schools when they reached school age. These days, there’s an increasing tendency to opt for charters or follow convoluted feeder patterns to DCPS schools west of Rock Creek Park. If the trend holds, Roosevelt won’t be a school that’s reflective of the neighborhood around it, but one for students who can’t find a way out.

The same issue is playing out across the city. The District’s population is growing rapidly, and young parents with money who in previous generations might have moved to the suburbs are often choosing to stick around to be near work and take advantage of life in the city. At the elementary-school level, these parents are becoming active in improving their children’s schools and recruiting friends’ and neighbors’ kids, too. But there’s a drop-off after that; only one neighborhood middle school and one neighborhood high school in the entire city enjoy a strong enough reputation to attract many families with the ability to choose. And so parents try to send their kids to those schools or put their fate in the hands of the charter-school lottery.

Roosevelt is far from the only underenrolled school. Dunbar and Cardozo high schools, for example, both moved into gorgeous, large modernized buildings this year, but Dunbar’s latest official student total is 504 and Cardozo’s 537—both barely higher than Roosevelt’s. Both schools, like Roosevelt, are in rapidly gentrifying neighborhoods where the ability to attract those new residents to the schools is still in doubt. And both schools have struggled with low test scores; at Dunbar, once the city’s premier high school for black students, only 17 percent of students are proficient in math and 18 percent in reading, even worse than Roosevelt’s numbers. Roosevelt isn’t alone in this trend. It’s just the most extreme example in some ways, with the lowest enrollment in a neighborhood undergoing arguably the most change.

It’s tempting to look at this issue as just a matter of race or income, of attracting middle-class white kids to poor majority-black and majority-Hispanic schools. There’s more to it than that. As the city’s school-age population grows, the question is how to ensure that neighborhood schools are truly schools for everyone, not just those who aren’t wealthy enough to move to the suburbs or go to private school, savvy enough to game the system, or lucky enough to win a lottery.

The next year and a half could provide the answer. In 2015, not only will Roosevelt students begin classes at their modernized building, but the city will also implement a revised boundary and feeder system that could reroute students to underenrolled schools like Roosevelt. How these changes are carried out will determine whether the new Roosevelt will rise on the fortunes of its surrounding neighborhood or continue to lose students and prestige to schools elsewhere that can claim better reputations.

Diane Rehm found her 55th high school reunion dispiriting. Returning to Roosevelt in 2009, the 1954 graduate saw a shell of the school she remembered so fondly.

“It just seemed so dark, so gloomy,” says Rehm, a Petworth native who now hosts the Diane Rehm Show on WAMU-FM. “It sure looked as though it had deteriorated greatly.”

When Rehm was a student, she recalls, the teachers were inspiring, the environs safe, the building immaculate, and the students’ bad behavior mostly limited to smoking cigarettes on the steps down to Upshur Street NW, to which the administration generally turned a blind eye.

“By today’s standards, I had at least a first-year college education at Roosevelt because it was such a fine school,” she says. “The teachers were absolutely outstanding. We were outrageously privileged in those years.”

Change came quickly after Rehm graduated. Her final year at Roosevelt brought the Supreme Court decisions in Brown v. Board of Education and Bolling v. Sharpe that turned a 100 percent white school—albeit a diverse one, with Greeks, Italians, Poles, and a large enough Jewish contingent to earn the nickname “Jewsevelt”—into a 0 percent white one in a matter of years.

But while the student body changed, the academics remained strong. Maurice Butler, who retired in 2010 after 35 years as a social studies teacher and administrator at Roosevelt, says that when he arrived there in 1975, the school was “99.99 percent” black but could still boast of delivering a top-notch education.

“Roosevelt, when I first got there in the ’70s, was a very good school with a good reputation,” says Butler, a Roosevelt loyalist whose study in his Petworth house doubles as a shrine to the school, with dozens of yearbooks and boxes of memorabilia and newspaper clippings. “It was an honor to go to Roosevelt.”

One of Butler’s early students, Isabel Wilkerson, became the first African-American woman to win a Pulitzer Prize in journalism. Many of the city’s power brokers were 1960s-era Roosevelt alumni: When Marion Barry’s third term as mayor spiraled into drug-riddled scandal, it was Roosevelt alum Carol Thompson who covered for him as city administrator, Roosevelt alum Rasheeda Moore who set him up, and Roosevelt alum Sharon Pratt Dixon who succeeded him as mayor.

The drug epidemic that snared Barry didn’t spare Roosevelt, and “things went into the toilet” in the early 1990s, Butler recalls. He stopped walking to work there out of fear for his safety, even though he lived just four blocks away.

“Things got really crazy,” he remembers. “We went into a huge nosedive where education wasn’t important. It was survival that was the important thing. I remember coming home and showing my wife where my insurance policy was.”

The school’s reputation tanked, and middle-school guidance counselors waived students away. So did Butler: His son wanted to attend Roosevelt, but Butler put his foot down. Enrollment dropped substantially, and violence consumed the school. In 1991, a Roosevelt senior out to lunch at a nearby carryout was kidnapped and killed. In 1994, students attacked a police officer patrolling the school’s halls. In 1996, an ROTC instructor at Roosevelt was badly beaten by a group of students when he told them to stop smoking marijuana in the hallway and go to class.

Those were the dark days; according to Butler and others, things took a turn for the better under Principal Learie Phillip in the late ’90s. But the upswing was temporary, and enrollment has tumbled again, from 812 in 2007 to 625 in 2010 to 473 last year.

That’s partly due to an abundance of new choices for parents. In 1996, acts of Congress and the D.C. Council allowed for charter schools in the District. In the 18 years since, the share of public school students attending charters has climbed to 44 percent. Charter schools, in a sense, provided an answer to the same kind of question that’s swirling around DCPS now: how to provide families that couldn’t afford private schools with a good, free option for their children. The result has been, in many cases, a better education for low-income D.C. kids—but it’s also precipitated the shrinking of the traditional schools, particularly middle and high schools.

Still, charters alone aren’t responsible. A second change also siphoned students away from neighborhood schools like Roosevelt. In 2009, the city revised its rules to allow students to attend out-of-boundary schools if they go to elementary or middle schools that feed into those schools. That’s enabled many students living near Roosevelt to cross Rock Creek Park and attend well-regarded Alice Deal Middle School and Woodrow Wilson High School. According to an analysis by the 21st Century School Fund as part of the boundary review process, 209 children living within the Roosevelt boundary attended Wilson last year—representing nearly half of the number of students who actually attend Roosevelt—in addition to the others who attend other neighborhood or application-based public high schools (plus the ones at charters).

Finally, some families simply cheat by listing a relative’s address or even renting a basement apartment in boundary for Deal and Wilson, says Jeff Steele, who founded and runs DC Urban Moms and Dads, the leading online discussion forum for local school issues. “Drawing school boundaries isn’t just like drawing voting boundaries,” says Steele, whose lives not far from Roosevelt but whose children attend Deal and a charter school. “If they told me to vote somewhere else, I would. If they told us, ‘Go to Roosevelt,’ we just wouldn’t go.”

The abundance of options for D.C. families highlights “the benefit and the cost of choice,” says Cathy Reilly, a Ward 4 resident and executive director of the Senior High Alliance of Parents, Principals, and Educators, an education advocacy coalition that’s met monthly since 1998. “We’ve adopted a philosophy of, ‘If you don’t like it, leave.’ When I was growing up, it was, ‘If you don’t like it, how can you make it better?’”

She adds, “I have the right to go to Deal and Wilson, and I live less than a mile from Roosevelt.” This system has likely been a boon for neighborhoods like 16th Street Heights, attracting families who wanted to send their kids to those west-of-the-park schools, but a curse for Roosevelt, depriving it of needed students. The area whose residents are entitled to attend Wilson now consumes nearly half the city, and Wilson’s enrollment tops 1,700 students. Roosevelt’s enrollment is barely a quarter of that.

Roosevelt students and staff don’t have to look far for a model of how to turn around a struggling school. Powell Elementary School, located just a block down Upshur, enjoyed a good reputation when Rehm went there in the late 1940s and when Butler attended in the early 1960s. But like Roosevelt, Powell fell on hard times as many middle-class residents, black and white, fled to the suburbs, and parents avoided it when they could.

When 16th Street Heights residents Andy Rowe and Patricia Abaroa were shopping around for a pre-kindergarten program for their son last year—families aren’t automatically guaranteed admission to their neighborhood school for pre-K, unlike for older grades—they felt as if there were a commandment, says Rowe: “Thou shalt not go to Powell. Hearst and Eaton [two elementary schools west of Rock Creek Park] are there for you.” Carla Ferris, who owns a pet-sitting business, was told by her sister who taught at Powell, “I would never want your kids to go here.” Martha Holley-Miers, a Petworth resident, drove by the school and thought it appeared on the verge of collapse. “Nobody that I knew really talked about Powell,” she says.

And yet all three have children at Powell. They were impressed by visits, increasingly positive word of mouth, praise on DC Urban Moms, and, in Ferris’ case, a change of heart from her sister, who told her, “This is a great school now.” Powell is so popular these days that the waitlist this year was 150 names long, at a school that enrolls only 33 to 73 students per grade.

What accounts for this abrupt turnaround? Parents gush about Principal Janeece Docal, who took over in 2009 and has aggressively courted neighborhood families with weekly Tuesday tours, Thursday coffee sessions, regular community walks, and appearances at local events. She calls family engagement one of her “main levers” for improving the school, and she’s been assisted by the Flamboyan Foundation, which works to get parents more involved in their children’s education and is in its second year partnering with Powell.

Until this school year, Powell students fed into MacFarland Middle School, and from there to Roosevelt. But the city closed MacFarland last summer due to underenrollment—Roosevelt is using the abandoned MacFarland building while it’s being renovated—and Powell graduates will now head to the Columbia Heights Education Campus and from there to Cardozo High School. That deprives Roosevelt of perhaps its most promising feeder elementary school at a time when Roosevelt needs all the motivated students it can get.

The only schools left to feed into Roosevelt are the West and Truesdell education campuses. Combined, those schools have just around 63 8th-graders to send to Roosevelt next year—a fraction of what the school needs to maintain its enrollment, let alone boost it to sustainable levels.

David Catania, who chairs the D.C. Council’s education committee and is contemplating a run for mayor this year, says the city has “dismantled the feeder system leading into Roosevelt through closures and redirections.” D.C. allocates education dollars on a per-student basis, so schools with fewer students have less money to spend on school-wide benefits like mental health services, librarians, and special course offerings. That in turn creates what Catania calls a “death spiral,” making the school less successful and less attractive to potential students, further diminishing enrollment.

Catania has accused Mayor Vince Gray’s administration of neglecting middle schools, which are mostly underenrolled as many elementary-school parents, sensing weak options for middle school, opt for the charter-school lottery when their children approach middle-school age. Last year there were 4,123 students enrolled in kindergarten at D.C.’s traditional public schools, but only 2,279 in 6th grade. DCPS Chancellor Kaya Henderson, who declined to be interviewed for this story, referred me in an email to a letter she wrote last month to the DCPS community promising a middle school plan as part of the fiscal year 2015 budget.

Some neighborhood advocates say it’s impossible to channel the energy of Powell at Roosevelt unless there’s a middle school to restore the old feeder pattern that established a quasi-campus of Powell, MacFarland, and Roosevelt, as well as the Petworth Library, in close proximity. “I don’t see how it can work without MacFarland,” says Reilly. “They have to reopen MacFarland. There has to be a middle-school option.”

But Deputy Mayor for Education Abigail Smith, who’s leading the task force that’s set to deliver recommendations in May for the first comprehensive redrawing of school boundaries and feeder patterns since the 1970s, says reopening MacFarland when Roosevelt moves back into its building in 2015 is “not something that’s currently on the table.”

Without reopening MacFarland, the most obvious way to boost enrollment quickly at Roosevelt is to change school boundaries or feeder patterns. That would most likely involve taking students away from overcrowded Wilson, perhaps in neighborhoods like Crestwood and 16th Street Heights, and depositing them at Roosevelt and other underpopulated schools. Such a move could run up against the law, since Wilson’s boundaries were drawn broadly for racial integration purposes, and would certainly anger residents of those areas who expected to send their children to Deal and Wilson. As a result, Smith says, a grandfathering provision will allow people to stay at their old schools for a time, though not so long as to “grandfather their grandchildren,” as some people want.

Of course, there is another way to boost Roosevelt’s enrollment, though it’ll take time. According to Smith, there are 2,000 high school–age children living within the Roosevelt boundary. Most of them are going to charters, out-of-boundary schools, or application-based public schools. But if Roosevelt can persuade even half of those students that they’ll get an equally good education there, the school’s enrollment problems will be solved. The solution is simple, if not easy to accomplish: All Roosevelt needs to do is become a better school.

Ivor Mitchell makes a habit of roaming his school’s halls in pinstriped suits and sneakers. The suits conform to the formality he projects: He addresses all staff members by their last names and introduces me to nearly every student and employee we pass as “Reporter Wiener.” The sneakers reflect all the ground he covers, both in the school and in the neighborhood, which he makes a point of exploring in the mornings after arriving from Baltimore, a daily commute that begins at 5:15 a.m.

Mitchell is in his fourth year as Roosevelt’s principal. He was the fourth principal of the school in six years when he arrived, and he faced skepticism about whether he’d really stick around after spending four years as principal of a Baltimore application-only high school. “That weeding-out process meant that we didn’t see all the students that a neighborhood high school sees,” says Mitchell. “And after four years and really wanting to be in education and wanting to make a difference, that’s why I got involved. I wanted to be in a neighborhood high school.”

Behind Mitchell’s studied formality is a burning intensity in his eyes, an almost missionary zeal for giving Roosevelt students every advantage enjoyed by their peers at higher-prestige schools. Working in an urban public school means confronting hundreds of difficult backstories, and Mitchell seems to know them all. He stops one student in the hall to ask about his recent attendance issues. The student’s absences are due partly to poor health and partly to his daily trek from Martin Luther King Jr. Avenue SE. But when Mitchell asks why he’s truant—a word Mitchell patiently defines—the student says he simply doesn’t own enough clothes to compile a daily outfit, and would prefer it if the school adopted uniforms.

Mitchell says his goal isn’t to be the best school in the city. He just wants it to be seen as a competitive option for families living in the neighborhood.

Nearly every neighborhood parent I speak to says that if Roosevelt is to rebound, it’ll need to establish special academic programs that’ll set it apart. Mitchell has a few ideas about what these could be, but he says his “main mission” is preparing students for college and careers. When Mitchell started at Roosevelt, he created a college and career center, with counselors to assist students with applications and decisions.

As soon as I arrive at the school for my first visit, we make a beeline for the center, which is clearly Mitchell’s pride and joy. It’s after 4 p.m., but the center is buzzing with students. Mitchell repeatedly boasts that nearly three-quarters of the senior class—a depleted bunch, since fewer than half of the school’s 9th-graders earn enough credits to continue to 10th grade—has already been accepted to at least one college, and it’s only January. Mitchell has created a wall of shame of sorts, a public list in the hallway of all the seniors who have not yet sent in college applications and filed them with the school. It’s about 35 names long.

I ask Mitchell what pitch he would make to Powell parents who might be uneasy about sending their kids to Roosevelt someday.

“We’re trying to send a message that, listen, we are a viable option,” he says. “I don’t want to be the principal that says, ‘We’re better than.’ What our message has been to all of these schools is, ‘If you’re looking for college and career, we are not void of that.’”

There’s evidence that Roosevelt is already improving. The school’s truancy rate—the percentage of students with at least 15 unexcused absences—dropped from 48 percent in the 2011-2012 school year, among the highest of the city’s neighborhood high schools, to 32 percent last year, among the lowest. The hallways during and between classes are quiet and orderly. And the support system Mitchell has put in place has given a sense of security to some students.

Senior Caiya Hawkins came to Roosevelt from Shaw Middle School at Garnet-Patterson, whose principal was murdered in 2010. “My principal got killed, so I didn’t want to get attached and get hurt,” she says. “But I met Mr. Mitchell and he told me what was important to get done. When I came here, the staff helped me get my grades back together, helped bring up my GPA.” Hawkins was recently admitted to Hampton University, which she plans to attend.

Roosevelt students feel the school’s poor reputation is a holdover from a more difficult past, one that doesn’t reflect reality today. “I have a lot of friends at [McKinley] Tech and Banneker [High School], and they think we’re not doing anything,” says Hawkins. “The work here is challenging.”

“I think people are stuck on the old reputation of Roosevelt, where there were fights every week,” chimes in senior Daquan Jones, who’s been admitted to three colleges and is awaiting word from his top choice, George Washington University. “But over the years, the dropout rate has decreased and the academics have improved.”

Changing the community’s perception of the school, then, is perhaps the biggest challenge ahead for Mitchell. He’s put together teams of staff members to pay visits to West, Truesdell, and Powell and promote Roosevelt’s achievements. He’s also reached out to the embassies of Ethiopia and El Salvador—the neighborhood has many immigrants from both—to market Roosevelt.

But some members of the community are skeptical that the school can turn around its reputation quickly. Ronald Hampton, a retired police officer and Petworth resident who served as Roosevelt’s PTA president and still volunteers there, agrees that Roosevelt’s bad rap is outdated. But he’s blunt about its prospects for attracting new neighborhood families who don’t fit the school’s racial or socioeconomic profile.

“It was the white folks who pulled their children out of schools ’cause they didn’t want their kids going to school with black children,” he says about the school’s change in the 1950s and ’60s. “I don’t think that those families are going to send their kids to Roosevelt or Coolidge [the other Ward 4 neighborhood high school] as long as those schools are 85 percent black.”

Still, the renovations could be a major selling point. The school’s staff and students have had to cope with difficult conditions in the crumbling building. Carey Hartin Dukes, who taught at Roosevelt from 2001 to 2008, remembers a week or two one January when the heat wasn’t working in much of the building, and she and her students had to wear hats and gloves in class. Butler recalls blackouts when students in his windowless basement classroom would pull out the cell phones they weren’t supposed to have for use as makeshift flashlights.

And the need for students to enter through the back of the building has been deeply demoralizing, Mitchell says. “It has been one of the most frustrating things for the students, for the community as a whole,” he says. “If I’m in Woodson [High School], I go through the front door. And then of course having a primarily African-American and Latino population at the school, that also sends certain messages of entering through the back, even to adults and staff. So this modernization, just the students and staff seeing the construction has been invigorating. They finally feel a sense of equality.”

Modernizations at other neighborhood high schools—Roosevelt will be the second-last to be renovated, with Coolidge to follow—have produced a bump in enrollment. Mitchell expects the same for Roosevelt. But parents say it’ll take more than a new building to attract them.

“If you give me a gleaming building with a lousy academic program, I’m not going to go there,” says Ferris. “The building is the icing on the cake. But you can’t have the icing without the cake.”

All the ingredients for a rejuvenated Roosevelt could be coming together now.The fact that the reopening of the building will coincide with the implementation of new feeder patterns is coincidental, says Smith, but it has the potential to be hugely consequential, giving the school a boost to its enrollment and reputation all at once.

Still, a new building and the addition of another middle school or two to feed into Roosevelt won’t solve the school’s problems alone, if many of the most motivated students and families who could be going there enter the charter lottery or finagle their way into Wilson instead. With nearly half of the District’s public-school students attending charters, this is a city-wide issue that threatens the basic concept of a neighborhood public school, and it’s one DCPS will have to confront, sooner or later. And Roosevelt, despite Mitchell’s claims to the contrary, will have to persuade the brightest kids in and around Petworth that it’s actually better than the abounding alternatives, not just an adequate fallback.

In some ways, Roosevelt is already succeeding beyond the school of 60 years ago. When Rehm attended, she recalls, nearly every student graduated, but only a third of them went on to college. (Rehm did not.) Now the majority of the senior class is college-bound. But in Rehm’s time, just about every child in Petworth went to Powell, MacFarland, and Roosevelt. Now the luxury of choice has made the neighborhood high school dispensable for many in the neighborhood.

Will the parents who helped revitalize Powell feel comfortable trying to do the same at Roosevelt? Ferris says that if things remain as they are, she won’t send her 4-year-old daughter to Roosevelt. “I don’t want to send her to a giant empty building where she’d be the odd man out,” she says.

Holley-Miers holds out hope that by the time her pre-kindergarten daughter reaches high-school age, Roosevelt might be a good choice.

“I would love that,” she says, “but I also know that a lot of things need to change.”