Two cities, on opposite ends of the country, both having suffered through a summer of civil unrest, are going to re-elect or replace their mayor in November. With a Black population of less than 6 percent, famously progressive Portland, Ore., has been roiled by protests and counter protests sparked by the killing of George Floyd in May.

Three thousand miles away, Richmond, Va., half of its citizens Black, also endured prolonged protests, many aimed at removing monuments to the Lost Cause, erected throughout the one-time capitol of the Confederacy. How the two mayors reacted to recent events in their city will surely affect their political futures.

With an election just days away, polls show that Portland voters are pretty much equally divided over who should be their mayor. Roughly a third of them favor Ted Wheeler, the incumbent. Another third prefer the much more progressive challenger Sarah Iannarone. The rest remain stubbornly undecided or are planning to write in someone else altogether. Wheeler could have prevented a challenge from Iannarone if he had garnered more than 50 percent of the primary votes back in May, as he had done in 2016. His re-election bid marks the first time in two decades that a Portland mayor sought a second term.

Oregon’s largest city has been a fixture of national news for months as nightly protests against racial injustice and police violence dominated news cycles. While Mayor Wheeler fends off attacks from the right, most notably from President Trump, urban planner and educator Iannarone comes at him from the left. She favors cutting $50 million from the $250 million police budget, far more than the $15 million already cut by Wheeler who has resisted calls for further defunding.

The mayor of Portland also serves as police commissioner. Wheeler admits mistakes have been made in law enforcement. Absent an alternative plan, he feels that further cuts to funding are inadvisable. Beside her calls to defund, Iannarone has made police accountability a major focus of her campaign, joining protests against police brutality and for racial justice. Her name has been linked to Antifa, something she does little to discourage. Perhaps in any other city, photos of her wearing a skirt decorated with the faces of Mao, Stalin and Che Guevara would be more of a problem.

If she should win, being mayor will be Sarah Iannarone’s first job in government. Besides reigning in the police, she will bring a passion for public transportation, commuting by bike and free Wi-Fi to the job. In her view, sex work should be legalized and non-citizens allowed to vote.

With more to offer than promises, Wheeler has a record to run on, not all of it favorable. Four years ago, he made ending homelessness a centerpiece of his campaign, pledging that no Portlander would be sleeping outside within two years. His self-imposed deadline has long passed, and the problem remains, in spite of an increase in available beds and services.

The sizable number of undecided voters will eventually have to choose between the two candidates, three if you count racial justice activist Teressa Raiford who is polling in single digits.

Police Chiefs and Statues Fall in Richmond 

Elected in 2016 as Richmond, Va.’s youngest mayor, Levar Stoney currently leads in a five-way race. Stoney ran as the education mayor four years ago and his current campaign is focused on transforming public housing. Critics point to the recent defeat of his multibillion-dollar downtown redevelopment plan as evidence he is willing to make deals with developers at the expense of the more pressing needs of the city. Several Democratic and Independent challengers saw this as an opening to oppose the incumbent.

Spring and summer protests led to clashes with Richmond police who were accused of using excessive force, leading to the resignation of the city’s chief. At one point, there were three chiefs of police in as many weeks, signaling a level of disfunction amid escalating violence. After promising a national search to find someone who would oversee reforms, Stoney deviated from the established vetting process by hand-picking a new chief. Ongoing protests and simmering tensions in the city are cited as reasons for the quick hire.

Richmond Mayor Levar Stoney faces four challengers in his bid for re-election. (Photo courtesy of Stoney Election Campaign)


It was Stoney’s removal of Confederate statues installed around the capitol city that put the mayor in the national spotlight. Initially, he was slow to react to rising popular sentiment against Richmond’s numerous monuments to the Confederacy. But once he made up his mind, all of the offending statues on city property were removed in quick succession, including those along Monument Avenue, a broad boulevard once lined with enormous memorials to Jefferson Davis, Stonewall Jackson and J. E. B. Stuart.

Mayor Stoney narrowly won a three-way race four years ago. Now, with four challengers splitting the rest of the votes, he holds a comfortable lead. A late-September poll put him 20 points ahead of his nearest rival. Nearly a third of the electorate remain undecided as time for them to commit to a candidate is running out. The result might not be known, but the race may be over before election day because Virginians have been voting since Sept. 18.