Back to Square One:
Reimagining O’Bryant Square

Back to
Square One:
O’Bryant Square

Randy Gragg
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Randy Gragg and the Portland Parks Foundation were determined to save Portland’s O’Bryant Square. With the help of some Loebs, they activated a citywide conversation and design charrette to generate bold ideas. Here’s Randy’s story.

Built in the 1970s to be a lively fountain plaza topping a subgrade garage, O’Bryant Square gradually turned into Portland’s most challenged public space. Early on, the membrane failed, leaking water into the garage and forcing the fountain to be shut off. As the landscape grew, so did hiding places and subcultures, drawing skateboarders, downtown youth, and revelers from the “Pink Triangle,” a collection of nearby gay bars with a vibrant night life. However, with no adjacent housing, a cluster of social service agencies took root nearby, and people-less “telco hotels”–where telecommunications businesses lease space for their computer equipment–sprouted on three sides.

Aerial view of O'Bryant Sq. as an active attractive park

In the 2010s, the plaza exploded in daytime life when the city’s first food cart pod grew to more than 50 vendors on the adjacent block. But the food carts were eventually displaced by a construction project: a new high rise combo of offices, condos, and a Ritz Carlton Hotel.

On the opposite corner, Multnomah County opened its first Behavioral Mental Health Center. The facility offered much needed treatment and shelter. But it often overflowed with more people than it could serve and drew more dealers, addicts, and mentally ill to the area. Finally, in 2018, owing to structural failures with the garage beneath, the city closed and fenced in the square.

Soon after the closure, the pandemic drained away nearby office workers and the manifold crises of houselessness, mental illness, and fentanyl overtook the city. O’Bryant became downtown Portland’s most blighted area. As the economic and social extremes unfolded, the square needed a new life. But Portland Parks and Recreation–PP&R–had insufficient funding and will to build a fully realized replacement.

Empty Sq. in the rain

As all this was happening, I was the executive director of the Portland Parks Foundation—PPF–and we were determined to reverse the park’s downward trajectory. PPF successfully lobbied the city to demolish the Square at a cost of $4.5 million and build a simple, inexpensive “interim park.” The budget for that was anticipated to be $1.5 million.

I brought the challenge of what next to the Loeb Fellowship Collaboratory, an annual alumni event at which Fellows volunteer ideas and specific actions to support community benefit projects. A number of alums pledged participation for a community design charrette, and I put together a powerhouse team. A generous Loeb Alumni Grant of $5,000 funded the travel and expenses for 5 Fellows to participate in 5-day charrette.

The Loeb Team was :

  • Christopher Calott ’11, Berkeley, CA; Robert and Millicent Lalanne Chair of Real Estate Development at UC Berkeley
  • Susan Chin ’99, New York, NY; design consultant and former director of Design Trust for Public Spaces
  • Roger Cummings ’09, Minneapolis, MN; chief culture producer and cofounder of Juxtaposition Arts
  • Damon Rich ’07, Newark, NJ; designer, urban planner, and partner at Hector
  • Jennifer Siegal ’03, Los Angeles, CA; founder of the Office of Mobile Design.

Additionally, Ed McNamara ’95 would facilitate a key session with property owners; Charles McKinney ’94 joined the charrette; and Kevin Cavenaugh ’08, Stephen Goldsmith ’00, and Eli Spevak ’14 participated in panels and workshops.

The prospect of Loeb expertise encouraged PP&R to embrace the interim park idea and to collaborate with Portland State University’s Center for Public Interest Design¬–well known for its tactical urbanist projects–as design lead. Those resources and monies leveraged an additional $150,000 in grants, sponsorships, and in-kind donations from government, foundations and firms focused on public interest, and neighboring property owners.

The result was Back to Square One: Reimagining O’Bryant Square (ROS for short). The name is a reference to Park Block One, the site’s label in Portland’s earliest plat map, and the hope for a fresh start.

Community Interests

Our goals were to understand the community’s hopes for this renewed downtown plaza and to envision simple, fast track draft designs and initial community programming to bring O’Bryant Square to life immediately after demolition. We wanted to foster the idea that this interim park would be an urban laboratory to understand what works and what doesn’t, in order to shape the future permanent design when funding to build a new park is identified.

Montage of photos of outreach activities.During March and April, 2023, ROS meaningfully engaged more than 1,000 Portlanders to offer ideas about how O’Bryant Square could be a harbinger of positive change. PPF gained generous media coverage that augmented robust social media outreach and attracted widespread interest. Six webinars, attended by over 650 viewers, paired the Loeb Fellows with local counterparts in the fields of community design, social services, mental health, urban youth, real estate, and pop-up architecture. A public survey garnered some 400 responses, and two community open houses offered further opportunities for idea generation and feedback. Additionally, we convened eight discussions with key stakeholders representing arts and culture; property owners; downtown youth; retail and hospitality; service providers; safety, management, and maintenance personnel; Behavioral Health Resource Center clients; and downtown residents.


Finally, the Center for Public Interest Design­ facilitated a charrette with 14 local professional teams that developed concept designs distilled from the community’s feedback and ideas. All the teams were intimately familiar with O’Bryant Square, the development goals associated with Portland’s Comprehensive Plan, and best practices for contemporary public space.

Their assignment was to develop a long term design concept and imagine an interim design and activation to serve as a first step. Nineteen fully executable designs emerged.

A Model for Public Engagement

While the effort focused on a single block, Reimagining O’Bryant Square became widely appreciated as the broadest, deepest, design focused engagement of Portlanders in years on the challenges and opportunities of the city’s downtown. City Commissioner Dan Ryan, who currently oversees PP&R, pledged to make use of the ROS findings, and he quickly seized on one: honoring the square’s queer history. During August’s Pride festival, Ryan rallied his fellow commissioners to rename the square Darcelle XV Plaza, just a few weeks after the death of one of Portland’s (and the world’s) most renowned drag queens, the late Walter Cole, aka Darcelle XV.

Darcelle with rhinestone jewelry

Ryan allocated $3 million in new funds for “activation of downtown parks.” He raised PPR’s initial allocation to Darcelle XV Plaza from $1.4 million in capital funds to $7 million for lighting, electrical outlets, and water and sewer hook ups to facilitate programming. Following this commitment and drawing on the charrette designs, CPID and PP&R began developing a plan that can be implemented through a change order to the demolition contract. PP&R has reached out to members of the LGBTQ+ community and briefed the Portland Design Commission and is on track to open what is expected to become a permanent park in fall 2024.

ROS succeeded in rescuing a critical downtown public space from the political quagmire that left it fenced and blighted for over five years. We provided a widely praised model for the public engagement of a broad spectrum of stakeholders, from power brokers and bureaucrats to clients of social services and street youth. Nothing like ROS had ever been done in Portland for a downtown public space. As a result of my involvement, I was tapped to lead the session on the future of public plazas and parks for Governor Tina Kotek’s Task Force on Downtown Portland.

Window showing display of Back to Square One ideas from community meetings

We elevated the discussion beyond Portland’s typical, sometimes parochial complaints and ambitions. We catalyzed a civic discussion that influenced the new parks commissioner to invest significant additional funds for urban plazas. The Loeb Fellows’ involvement both in the prefatory Zoom talks and in the weeklong charrette were an inspiration for the public, the bureaucrats and politicians, the students involved, and the members of the local design teams.

There are challenges ahead. At the insistence of the Ritz Carlton, Commissioner Ryan plans to permanently fence and gate the park, but no one really knows how Portland’s first fenced urban public space will work. In any case, strategies will need to be developed to deter drug dealing and usage or camping. Funding is still needed from public or private sources to program Darcelle XV Plaza. Many ROS participants hoped to offer programs in the plaza, but they have not yet been engaged. The queer community—with a nudge by members of the ROS team and Darcelle’s fellow drag queen Poison Waters—is beginning to talk about activating the plaza. With luck, the former O’Bryant Square can live up to its new name, inspired by one of the most colorful, generous characters to ever have called themselves a Portlander.