Ted Wheeler celebrates his victory in the race to become Portland mayor at Blitz Ladd, a sports pub in Southeast Portland, on May 17, 2016.
Bradley W. Parks / OPB
Ted Wheeler held his election night party at the Blitz Ladd sports bar in Southeast Portland. Early on in the night, Wheeler's supporters watched basketball superstar LeBron James lead his Cleveland Cavaliers to a 30-point blowout playoff win as they waited for the balloting to close.
Yet, Wheeler ended up outperforming even King James — winning the Portland mayoral race by almost 40 percentage points.
Wheeler was the best-funded and best-known candidate in the race by a wide margin. Shortly after he entered the race in October, Mayor Charlie Hales, the first-term incumbent, decided not to seek reelection.
In a year in which the political conversation has been dominated by the presidential primaries, none of Wheeler’s competitors found a way to stand out in the crowded field.
Wheeler's campaign fared better in generating news coverage. In February, after the Oregonian/OregonLive.com cancelled a planned debate between just Wheeler and Bailey amid threats of a protest, he led the effort to pull together a replacement forum featuring most of the candidates. The campaign also set up unique meet-and-greets with constituents in the community, including several in East Portland.
Jules Bailey gave up a chance to seek reelection to the Multnomah County Board of Commissioners in order to run for mayor. Although Bailey succeeded in winning several major endorsements, including from the Portland Police Association, the Portland Association of Teachers and the Oregon League of Conservation Voters, he never succeeded in establishing himself as the clear progressive alternative to Wheeler, who earned every major newspaper endorsement and the backing of the Portland Business Alliance.
Related: Ted Wheeler Says Housing Will Be His Priority If Elected Portland Mayor
By election night, the Bailey camp was privately lowering expectations of his performance, and key adviser Stacey Dycus didn't attend his campaign party.
"Ted Wheeler, I’ve said from the very beginning, is a great man," Bailey told his supporters. "I believe he is fully ready to be mayor of Portland. And that he understands the issues that Portlanders are facing."
The campaign focused on homelessness, Portland’s ongoing housing crisis, infill, various attitudes toward police reform and poverty.
The remaining field was dominated by political newcomers and serial candidates.
Jules Bailey delivers remarks to supporters and the media after losing his bid for Portland mayor.
Aaron Scott / OPB
One novice who made a surprising impact was Sarah Iannarone, a café owner and Portland State University employee. She made smarter growth and safer streets the cornerstones of her campaign.