Portland Mayor Ted Wheeler reacts after being exposed to tear gas fired by federal officers while attending a protest against police brutality and racial injustice in front of the Mark O. Hatfield U.S. Courthouse on July 22, 2020 in Portland, Oregon.
CNN  — 

For the last 90 days, the city of Portland, Oregon, has been home to protests – some peaceful, others violent – on its streets. The protests began after the death of George Floyd in Minnesota and have continued nightly since then.

At the center of it all is Ted Wheeler, the Democratic mayor of Portland. Of late, Wheeler has become a favorite punching bag for President Donald Trump, who blasted him Sunday as a “fool.” Wheeler shot back that Trump had “created the hate and the division” in the country.

In search of more about Wheeler, his fight with Trump and the Portland protests, I reached out to Jeff Mapes, a longtime political reporter at the Oregonian and now a senior political reporter at Oregon Public Broadcasting.

Our conversation, conducted via email and lightly edited for flow, is below.

Cillizza: Let’s talk about Ted Wheeler *before* these protests began 90 or so days ago in Portland. What was the general impression of him? Where did he come from?

Mapes: Wheeler, who comes from a wealthy timber family and was once state treasurer with statewide ambitions, has had his struggles since he was elected mayor in 2016. Partly, this is because it’s one of the toughest jobs in Oregon politics. His last three predecessors quit after just one term in office. (Portland has a very unusual form of local government.)

OK, enough political science. Local politics took a decided turn to the left during Wheeler’s stewardship and he’s struggled to respond to it. City Council meetings have frequently devolved into shouting matches, with demonstrators packing the chambers to argue about police shootings, homeless policies and more.

At one point he was heard publicly grumbling that he couldn’t wait for his term to be over. He is running for re-election this year and he came very close in the May primary to getting the majority vote he needed to avoid a runoff. His opponent is Sarah Iannarone, a local activist who is running to the left of Wheeler and has been a frequent participant in the protests. (Teressa Raiford, a Black protest leader, is also running a write-in campaign for the job).

Cillizza: Now, since the protests began: What’s been the perception of how Wheeler has handed all of this?

Mapes: Many activists deride him for not supporting bigger cuts in the police budget – defunding, if you will – and for allowing the Portland Police Bureau (which he directly oversees) to routinely use tear gas in the first weeks of the protests. They called him “Tear Gas Teddy.”

At the same time, conservatives and many in the business community complain he hasn’t done enough to stop the non-peaceful side of the protests: the vandalism, arson and violence against police (such as the throwing of projectiles and shining of laser lights in their eyes). Wheeler did support some cuts in the police budget and worked with Commissioner Jo Ann Hardesty, the lone Black member of the council and a longtime police critic, to place a measure on the ballot setting up an independent police review system.

Cillizza: Prior to Trump wading in, was Wheeler taking heat from either other city pols or statewide pols? If so – who and why?

Mapes: He and Hardesty have warred at times, and she’s repeatedly urged him to give her control of the police bureau.

Also, remember, we’re now in Round 2 of Wheeler’s cage match with Trump. The first was in mid-July, when the administration moved Department of Homeland Security police units into Portland, ostensibly to protect the federal courthouse and other US government facilities. That’s when you started hearing reports of federal cops pulling demonstrators off the street and shoving them into unmarked vans. The feds also stepped up gas attacks on demonstrators to a level never seen in an American city.

The federal intervention – and Trump’s predictable inflammatory statements – gave the demonstrations new life and swelled the crowds. Wheeler gained national publicity when he showed up outside the federal courthouse one night to withstand the gas attacks. He was derided by many protesters, but it’s fair to say it was useful to him politically. And it did seem to affect him – he came away saying that he realized how ineffective the ubiquitous tear gas attacks were in deterring demonstrators.

In the end, though, Wheeler wasn’t the one who found a way to get the federal forces off the front line. That was Democratic Gov. Kate Brown (who ironically first won her job by replacing a resigning governor, ending Wheeler’s own hopes to run for the job). Brown brokered a deal to replace federal forces on the front line with Oregon State Police troopers, and that did seem to quell tensions for a while.

Cillizza: Trump attacking the mayor of Portland would seem, on its face, to be good for Wheeler’s politics. True or untrue?

Mapes: One local pollster, John Horvick, that I talked with quipped that Trump’s attacks on Wheeler should be listed as an in-kind contribution to the mayor’s re-election campaign. And in his press conference Sunday, Wheeler was happy to repeatedly fire back at the President and urge him to drop his divisive rhetoric. But he was light on what he was going to do moving forward. And, once again, Brown was the one with a concrete plan. She announced “a unified law enforcement plan to protect free speech and bring violence and arson to an end in Portland.” It includes bolstering the Portland police with forces from other local police agencies and the Oregon State Police, with further help from the FBI and the US Attorney’s office.

Cillizza: Finish this sentence: “The Portland protests going national is a _________ thing for Ted Wheeler.” Now, explain.

Mapes: I’m sorry, I got out of the political prediction business following the 2016 election. As you thought, standing up to Trump is always good politics in Portland. But the loss of life (not just on Saturday, but in the rising number of shootings around the city recently) leaves the sense of a city spiraling out of control. That is not good for him. He’s probably still the favorite for re-election, but Portland voters are known for dishing out electoral surprises. One thing seems pretty clear: he can forget statewide political office. Darn it, there I go again, making predictions.