To track the movement of new money across the District, just follow the plate glass. Start out near 14th and P Streets NW, at dusk, outside the Whole Foods outlet. Its towering windows throw light everywhere, as if the grocer were seeking to bless neighboring properties with its rays. A Washington Post writer once called the place “a 61,000-square-foot cathedral that cast its auric glow over P Street NW.”

The chain stores—Starbucks, Ann Taylor, Restoration Hardware—all cast that same glow, putting their inside workings on display. So do the chain homes. Look at any loft condo development in and around downtown: The exposed concrete and exposed ductwork are all exposed to passers-by through colossal windows.

But when the gentrifiers look out their own windows, they see a different tableau. Amid the acres of glass sit the homes and businesses of the holdout class.

The holdouts are the guys who’ve watched the boom through small windows. Those small windows may be attached to a town house near Logan Circle, a print shop next to the MCI Center, or a home bordering on the District’s toppled public-housing projects. Before the wide-eyed gaze of new buildings, the old buildings hunker down and squint.

The holdouts aren’t necessarily more noble than their gentrifying neighbors. Some of them may be more greedy—waiting until someone offers millions of dollars for their newly fashionable hovel. Some may just be clueless: What real-estate boom?

But they make the city a city. Historians will tell you that Pierre L’Enfant planned the District of Columbia. And he did, in a way. He came up with the spokes-and-grid thing, the wide boulevards, and the quirky park spaces.

Property rights, though, have limited L’Enfant’s sway over the cityscape. From block to block, the District comes off like a place with no blueprint at all. Today, it consists of about 173,000 property lots.

That means that in a city of just 69 square miles—a speck on the mid-Atlantic regional map—there are 173,000 opportunities to mold the streetscape in your own image: façades that can be painted blue, white, or rose, or surrendered to the ivy and the elements; stoops that can be sheltered with green awnings or regularly coated with dog piss; front yards that can host azaleas and rhododendrons, or cigarette butts and empties; cast-iron fences that can be festooned with old-school architectural niceties, or—fuck it!—chain-link.

Every so often, the city’s Office of Planning churns out something called “Comprehensive Plans” for the wards and neighborhoods. These documents bespeak neighborhood consensus on the makeup of each commercial strip and how many apartment buildings it can absorb.

But there’s no plan here. Planning doesn’t juxtapose a 7-Eleven with pricey apartments. It doesn’t pair a weather-beaten, century-old town house with the headquarters of National Public Radio. And it doesn’t put a downscale fish-fry next door to the city’s priciest supermarket.

Planners aren’t that smart. That’s why we have holdouts. —Erik Wemple

Art accompanying story in the printed newspaper is not available in this archive: Photographs by Darrow Montgomery.