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The politics are different, but both are liberal cities.
Different in racial diversity.
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Sadly, those two items are tied directly together.
It is no coincidence that Portland's big divergence from the typical US city started in the late 1960s -- the era when many cities were in race relations crisis. Portland's overwhelmingly white population, and in particular very small African-American community had practical political consequences. The pressure for 'white flight' was much lower, so the speed at which the city emptied out into the suburbs was lower, and the 'flight' was often not very far (e.g., for my grandparents it was 2 miles, 12th and Fremont to about 55th ave). The political system was not overwhelmed with racial issues, nor was a big split in the liberal-activist community over what to prioritize. There was space for metro area politics to focus on land use planning and transportation rather than busing and housing fairness and crime. I imagine improving pedestrian safety took a back seat in Boston City Hall when they were dealing with riots over busing.
Had Portland's AA community been somewhat larger, and become more visible in pushing for fair treatment, you would seen the balance on the City Council tipped towards conservative law-and-order candidates. Frank Ivancie would have won in '72, not Goldschmidt. Add in the additional white flight and you get a Portland with more freeways and more suburbs.
If Portland had a lot more minorities, there might well have been a Black Mayor, or at least City Council and School Board members as early as 1970. Evidence from other metro areas shows that when that happened, white flight skyrocketed -- people felt they had to move entirely outside the city limits, not just to a neighborhood where no minorities lived. Regional cooperation between cities becomes impossible and there is little willingness of the suburban areas to invest in the central core. Portland vs St. Louis is a useful comparison here.
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