most left wing major city in America

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I would say San Francisco, without a doubt. The other cities mentioned are quite Democratic, but they do not have a political culture nearly as liberal as San Francisco. Politically, San Francisco would be a moderately liberal European city.

No, No, No, No!
San Fransisco would be THE most liberal city in Europe, except perhaps for Amsterdam. SF would easily be contender for the most socially liberal city in the world. I don't know why people think Europe is that liberal. It isn't.
Even London doesn't have the whole huge hippy/gay/counter cultural element prevelent in some US/Canadian cities. Places like Toronto, SF and Seattle are easily more socially liberal than London, and probably fiscally too.

Basically this. And Toronto isn't as leftist as San Francisco. After all, Toronto has a functional Liberal Party.

Though I argue Marin County may be more liberal than or equal to San Francisco. San Francisco has a large immigrant community that is very Democrat, but not in sync with the whole hippy/gay/countercultural element. Hell, several precincts of San Francisco actually voted FOR Prop 8. About 25% of the city actually. The same margin as in Marin County.

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Portland might not be the most Democratic city but it's arguably the most leftist city (yes, even on economics). It's not upscale outside of a few hilly neighborhoods on the westside and has a disproportional large lower middle class alt community that I'd argue is lacking in SF and Seattle. If we had a significant left-wing third party candidate ala Nader in 2000, Portland would probably give him/her the largest percentage of the vote at this point. Portland keeps attracting more and more young adults without gentrifying rapidly.

Also, Portland is really really really really white. Which might make it less Democratic but makes it more liberal, since cities like SF and Seattle still have large minority populations who are largely more moderate-leaning.

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anyone who thinks NYC is the most liberal city in America has never been to 75% of the neighborhoods in the city.

not to mention the Mayor is one of the top 2-3 financial magnates in the country with a $22b net worth.

Yeah. NYC elected Giuliani and Bloomberg. Yes, they are very moderate Republicans. But how many cities in America would ever elect a Republican under any circumstances? Would San Francisco, Portland, or Madison ever do so?

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I'm surprised no one has mentioned Oakland. And does Berkeley count? In that case it it is the most left-wing city in America.

Isn't Richmond slightly more liberal than Berkeley?

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San Francisco is not the most liberal city. You see, Matt Gonzalez actually lost. A large hispanic/asian population in SF makes it more Democratic than liberal, because there most moderate hispanics/asians vote Democrat.

On the other hand, nearby Richmond actually did vote in a Green. And Berkeley is only slightly less liberal than Richmond.