There is a lot to unpack when it comes to Curtis Sliwa, the Republican who has run for mayor of New York City two times. You'll always be able to spot Sliwa in a crowd due to his signature red beret.

Boy, those were the days.” That’s how Curtis Sliwa, former New York City mayoral candidate and Portland mayoral hopeful, greeted me outside his apartment for a day of Rose City sightseeing. Sliwa, 71, ...