Mayor Ted Wheeler’s office is not known for its transparency.
Granted, mayors’ offices are never as transparent as the public (and the press) would like them to be, but since day one, Wheeler’s team has remained remarkably closed-off to outsiders—including city hall employees working just a floor below. Meanwhile, the limited info that does trickle out of Wheeler’s office drops at seemingly random times, and often contradicts other statements coming from his staff.
In the words of Marshall Runkel, chief of staff to Commissioner Chloe Eudaly: “Disagreement and debate is inevitable and healthy... but [our offices] could work together more effectively if the mayor’s office spoke with one voice.”
There’s no easy explanation as to why Wheeler’s seemingly cloak-and-dagger office functions the way it does. But, as with most workplace problems, it’s easy to point fingers at whoever’s in charge. Up until Friday, that person was Wheeler’s enigmatic chief of staff, Maurice Henderson.
Next week, Henderson, who held the chief of staff position since Wheeler entered the mayor’s office in 2016, will start a new job as TriMet’s Chief Operating Officer. He’s since been replaced by Wheeler’s communications director, Michael Cox.
While Cox’s promotion might not fix all of the puzzling problems coming from Wheeler’s office, it’s as good of an excuse as any to examine the role a chief of staff plays—or should play—in the mayor’s office.
“The mayor’s chief of staff sets the tone for the entire mayor’s office,” says Tim Crail, chief of staff for Commissioner Amanda Fritz.
According to Sonia Schmanski, chief of staff for Commissioner Nick Fish, the ideal chief of staff in the mayor’s office is “someone who wakes up every morning thinking about the best way to help all of council reach the right outcome.” That person should also treat the other commissioners’ chiefs of staff as their primary colleagues, not distant coworkers. I’ll let Schmanski’s wonderfully macabre analogy explain this better: “We’re all flies on the same spiderweb,” she says. “Every move one of us makes affects all of us.” (Note: Schmanski doesn’t think this is a great analogy. “Who’s the spider?” she asks—a question that only improves this analogy.)
Schmanski adds that it can also be useful when the chief of staff is actually present.
Famously, Henderson didn’t check that box. According to multiple city hall staffers who asked to remain anonymous, Henderson was one of the most absent chiefs of staff for a Portland mayor.
“[Henderson] functioned as an ambassador for the mayor’s office... both within Portland and around the world,” says one. “He was not as visible within city hall as I expect Michael [Cox] will be.”
Unlike Henderson, Cox has a background in communications, something that city staff say could detangle the clarity issues that have plagued Wheeler’s office. (That said, ask any Portland journalist about the matter, and they’ll say Wheeler’s current communications team—run by Cox—could use some refining, too.)
Cox also has a history with the mayor that Henderson lacked—he ran Wheeler’s communications team both when Wheeler was state treasurer and when he ran for mayor.
Time will tell if that will make Cox a savvy manager or another yes man. Regardless, the changing of the guard should allow for some intentional tweaks to the office’s current status quo. It’s an opportunity for Wheeler to start fresh with Portlanders, his fellow commissioners, and the press. (Hi!) Because in Portland, every move Wheeler’s office makes affects us all.