Reflecting on the Past, Present, & Future of Portland's Pearl District

By Randy Gragg

The following excerpt is reprinted with permission from the September 2015 issue of Portland Monthly.

On a warm evening shortly after I arrived in Portland, an artist friend toured me around “places I should know about.” The year: 1990. The neighborhood: close-in Northwest. We savored the glittering, inner-city industrial spectacle of aluminum dunked at a galvanizing plant. We knocked back bourbons with the Radio Cab drivers at Yur’s. And then we wandered to the highlight: the decades-old, Greek-myth-inspired graffiti adorning the concrete columns holding up an elevated roadway then called the Lovejoy Ramp.

In hues of cerise, orange, and peacock blue, chalk lines and swabs of paint climbed the pillars like vines, conjuring mythical owls and beasts, fanciful flora, and a portrait of Diogenes, lantern hoisted high. Drawn circa 1950 by a classically trained Greek immigrant and night watchman, Tom Stefopoulos, the artworks had memorable cameos in Gus Van Sant’s Drugstore Cowboy in 1989 and would later appear with Elliott Smith in a short film called “Lucky 3.” Like some sort of hobo version of the Chauvet Cave, they seemed sacred. An introduction from a knowing local felt like a rite of Portland passage.

A few blocks away, a place we now call the Pearl District was germinating. Eventually, this new neighborhood was destined to displace the columns—along with most of that lost-city grit my friend and I toured—with a globally celebrated example of innovative urban redevelopment. 

Over the ensuing decades, as a journalist and critic covering architecture and development, I’d write about the neighborhood’s rapid transformation—and about the columns’ plight.  

Today, as buildings rise on the last of the Pearl District’s empty land, and plans commence for 12 more blocks next door as the huge central US Postal Service facility prepares to move, it’s a good time for reflection—on the fate of Stefopoulos’s paintings and the quality of the gradually maturing neighborhood.


Timing is everything. When the Great Recession rolled in, unlike so many cities (or other Portland neighborhoods—say, South Waterfront), the Pearl had comparatively few condos left unsold. [Peter] Stott and his partners nicely timed the sale of three Brewery blocks for a local record of $292 million—in 2007, moments before the economy’s wheels spun off. Even the Lovejoy Columns enjoyed a little of the boom’s final months: developer John Carroll installed two of them in a plaza adjoining his sold-out condo development, the Elizabeth. 

For the Pearl as a whole, the recession was less a crash than a historical dividing line between “Early” and “Late.” The two eras share a common DNA of parks and streetcar and Portland’s compact 200-foot blocks. Beyond that, they are increasingly distant cousins.

In the Early Pearl, some “streets” became landscaped pedestrian corridors threaded between residential buildings. In a market hungry for condos, architects refined a template that, on the tiny blocks, maximized sunlight into every unit: essentially a six-story version of the courtyard apartment. Aging baby boomers and well-heeled Gen X creatives came in droves. Writing in the Oregonian at the time, I noted that the developers had nicknamed the monoculture of buildings “the Pentagon,” and I raised doubts about failure to focus retail on single corridors to create more urban energy. But with 15 years of hindsight, I now think those buildings offer lovely, neutral backdrops to the lush gardens and tree-lined streets. The scattered retail creates a charming sense of discovery, like Parisian side streets. The Early Pearl is essentially a garden district, with a graceful coherence as distinct as the hexagonal apartment blocks of Barcelona’s Eixample district.

Stretching north of NW Pettygrove, the Late Pearl is rising in a different form. Gone are the green streets. The shorter buildings have grown bloated, the courtyards more pinched. Towers are rising, skinned in reflective glass. All but one of the new buildings recently finished or under way are rental apartments, meaning the residents (and in many cases, the developers) won’t be there for long. Retail has become more lonely than charming. Long envisioned as a chance to add some historical texture to the district’s gleaming newness, Centennial Mill has sadly been neglected by its owner, the PDC. With redevelopment plans stalled, parts of its decaying carcass will continue to be demolished this year.

Asked whether there were gods, Diogenes replied, “I do not know; only there ought to be gods.” The same might be said of city planners.

Stefopoulos’s portrayal of the philosopher now sits on a concrete column crowned by remnant rebar—a “place you should know about” for many organized history tours. The Pearl District, by most measures, particularly those of similar urban redevelopments of other American cities, is an enviable success. Since 1991, the district has gained more than 9,000 housing units. Hoyt Street Properties, thus far, has built 150 housing units per acre. But as in other cities, affordability is a problem. The first new condo building to rise since the crash is 80 percent sold, at an average $700 per square foot. Thus far, developers and the city have fallen short of the 30 percent affordability goal by 123 units.

On a recent summer evening, I walked the Pearl with the 1983 “Last Place in Downtown” study in hand. Most of the plan’s drawings of expansive office parks missed the future, by a lot. But NW 13th Avenue unfolded in renovated historic buildings with shops and restaurants spilling out on their loading docks and pedestrians freely walking in the street—just like the picture. Hopefully, the Late Pearl’s patina will mature to match its older cousin’s, and the dealmakers and architects who shape the old US Postal Service’s 12 blocks will plan and draw pictures—but also work it out, competing and reinforcing, on the ground.

Randy Gragg is the Director of the John Yeon Center for Architectural Studies at the University of Oregon. Click here for his feature in its entirety, reprinted with permission from Portland Monthly.