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O’Bryant Square has languished for nearly four years, as the city of Portland has struggled to devise a workable, funded plan to redevelop the half-block plaza in downtown.

Now the city has put forward a proposal to redevelop the square that would rely in part on a $5 million federal grant. The city would contribute an additional $4.44 million to revitalize the park space between Southwest Park and Ninth avenues, and Washington and Harvey Milk streets.

The Portland Office of Management and Finance submitted a grant application to the U.S. Economic Development Administration (EDA) on Jan. 28, requesting $5 million in funding from the American Rescue Plan Act. The plan was forged by three city bureaus: Parks and Recreation, Transportation, and Planning and Sustainability.

The city would use the funding, if awarded, to demolish the structurally unsound 21,000-square-foot parking garage. Public engagement, design and construction to rebuild the half-acre park would follow, according to a copy of the , which was obtained through a public records request.

The $9.44 million project budget also calls for construction of Green Loop street improvements in the area; the Green Loop is set to connect to the Ankeny West food cart pod a couple of blocks north of O’Bryant Square. Portions of the Green Loop would wrap around the square on Southwest Ninth Avenue and on Southwest Harvey Milk Street, providing pedestrian and bicycle routes as well as public space.

The city also wants to use some of the federal funding to improve and make permanent Pride Plaza 鈥� an LGBTQ-friendly area in the West End. Pride Plaza sprang up during closures resulting from the COVID-19 pandemic. Portions of Southwest Harvey Milk Street were closed to vehicle traffic as the pandemic took hold in 2020, and nearby businesses erected outdoor seating.

City officials abruptly fenced off O’Bryant Square on March 5, 2018, citing structural deficiencies related to the underground SmartPark garage. The public plaza has since continued to deteriorate. It’s increasingly incongruous as more than a billion dollars in new development rises nearby, including the $600 million, 35-story Ritz-Carlton tower under construction diagonally across Washington Street, and the 25-story Eleven West building two blocks west.

Downtown business interests are eager to see the city move forward after years of inter-bureau wrangling and inaction.

鈥淥bviously, O’Bryant Square itself, it’s very important that gets reopened,鈥� said Matthew Goodman, vice president of Downtown Development Group, the developer of Eleven West. 鈥淚t’s been far too long.鈥�

Walt Bowen, CEO of BPM Real Estate, the developer of the Ritz-Carlton tower on Block 216, declined to answer questions. A spokesman, Pat Walsh, stated in an email: 鈥淎 new park will greatly benefit the Green Loop.鈥�

Development of O’Bryant Square would leave residual floor-area-ratio development rights that could be sold to a private developer, according to the city’s application. The city would dedicate any revenue from the sale of FAR to the project’s matching funds. The city estimates the project would create 205 jobs and help retain 84 jobs.

The grant process is competitive, an EDA spokesman said. Portland’s application will be evaluated by an investment review committee, and if successful, will advance to the agency’s assistant secretary for final approval.

Portland’s Hennebery Eddy Architects has done pro-bono design work to show what O’Bryant Square could become. The firm’s office in the Pittock Block overlooks the plaza.

鈥淗ennebery Eddy is strongly in favor of moving the demolition and redesign of O’Bryant Square forward as soon as humanly possible,鈥� Tim Eddy, president of the firm, stated in an email. 鈥淭he square has been in a steady state of decline for more than three decades and is in a critical location in downtown relative to surrounding historic buildings, new development and the Green Loop.鈥�

Design and development would begin this year, with construction scheduled to wrap up in July 2027, according to the grant proposal.

Some observers said they were frustrated by the lengthy delays.

鈥淏y the time O’Bryant Square is completely redeveloped, it will have probably been close to a decade at that point,鈥� said Iain MacKenzie, who runs the Next Portland architecture and development blog. 鈥淣onetheless, I think there’s a great vision there.鈥�

Mark Ross, spokesman for Portland Parks and Recreation, stated that the lack of funding for garage demolition has held up the project.

鈥淭he proposed schedule reflects the complexity of the project and the remaining due diligence, design, resource development, engineering and engagement work required to support construction,鈥� Ross stated. 鈥淥nce funded, PP&R will work with city partners to expedite project delivery.鈥�

Commissioner Carmen Rubio has allocated $3 million in parks system development charges to expand capacity at O’Bryant Square.

Portland should carefully consider engaging a landscape architect to turn the temporary improvements at Pride Plaza into a lasting public space, MacKenzie said.

鈥淲e very rarely do very high-quality public realm projects in Portland,鈥� he said. 鈥淚’d love to see something that really did redevelop Harvey Milk and make those two, potentially three, blocks really a pedestrian-focused and inviting public realm that people would specifically go to, to visit.鈥�

Food-cart advocate Keith Jones has been working to relocate carts to the area between O’Bryant Square and East Burnside Street. He sees the Green Loop improvements as part of the Cart Blocks concept, formerly known as the Culinary Corridor, connecting the Ankeny West pod to O’Bryant Square. The concept originated when more than 50 food carts were evicted from Block 216 to make way for the tower.

Jones is looking to possibly install shipping containers on Ankeny Street between Southeast Eighth and Park avenues that would host retail businesses. Another idea he’s floated is to station a double-decker bus at Burnside Street with service of coffee in the morning and alcohol at night.

鈥淚’m looking at it as an opportunity to continue to extend resilient outdoor businesses toward O’Bryant Square and connecting it to Ankeny West,鈥� he said.

The block has some flaws. Architects who have studied O’Bryant Square point to dead zones to the north and east: the blank walls of the Union Bank Building and a CenturyLink telecommunications building, and a small parking lot.

鈥淚f the grant’s successful, it’s an opportunity to start over with an urban park that has had a difficult, troubled history, and it’s an opportunity to enliven a part of downtown that is extremely challenging,鈥� said Randy Gragg, executive director of the Portland Parks Foundation.