Here’s a test. You are a developer looking to do a big project in Portland. Who do you talk to?
The city manager? He’s important, but he is an administrator, not a policy maker.
The mayor? You should probably give him a call, but realize that he has another full-time job and won’t be able to put much energy into your proposal. Plus, take a good look at the calendar because the mayor’s term starts in January and effectively runs out of steam around Election Day.