Former Portland Mayor Sam Adams is seeking a political comeback. And he’s challenging an incumbent.

Adams filed Wednesday to run for the Portland City Council seat held by Commissioner Chloe Eudaly, who is seeking reelection in the May primary.

Portland Mayor Sam Adams is shown at City Hall in Portland, Ore., Friday, Dec. 16, 2011. 

Portland Mayor Sam Adams is shown at City Hall in Portland, Ore., Friday, Dec. 16, 2011. 

Don Ryan/AP

Adams was a longtime chief of staff to Mayor Vera Katz, and a city commissioner when he was elected the first openly gay mayor of a large U.S. city in 2008, a win many political observers saw as the next step on the path to state or federal office. 

But his administration was marred by scandal: As he was preparing to run for mayor, Adams denied rumors that he’d been involved in a sexual relationship with a 17-year-old former legislative intern, Beau Breedlove.

Soon after his election, as Willamette Week prepared to publish a story, Adams acknowledged he and Breedlove had been in a sexual relationship, though he said it took place after Breedlove turned 18 and reached Oregon’s age of consent.

The Oregon attorney general’s office investigated the relationship, but did not charge Adams with any crimes. Breedlove told investigators, according to their report, that he and Adams kissed at least twice before his 18th birthday, including in a City Hall restroom. State prosecutors said they could not corroborate that account and questioned Breedlove’s credibility.  

Adams opted not to seek reelection in 2012. As a mayor and city commissioner, he was known as a creative and vigorous supporter of the arts and pedestrian — and bike-friendly planning. He showed a willingness to work with the real estate and downtown business communities, which have a sometimes-contentious relationship with City Hall.

After leaving City Hall, Adams served as head of the City Club of Portland for several years and then moved to Washington, D.C., to work for an environmental think tank. He returned to Portland last year and told Willamette Week he’s struggled to find work because of a sexual harassment complaint a former aide filed in 2017.

Rumors of Adams running for city office again have been circulating for several weeks, though conventional wisdom was that he would run for the open seat created by the death of Commissioner Nick Fish earlier this month. Adams’ decision to challenge Eudaly, a champion of tenants’ rights who has angered many in the real estate community with her pushes for renter protections, is a surprise given the uphill climb any candidate faces when trying to unseat an incumbent.

Eudaly has her own experience facing off against the power of incumbency: She won her seat four years ago by defeating another controversial sitting commissioner, Steve Novick.