He wishes to invade Portland because he figures the drugs are coming in through all the ports
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Portland Oregon was named after Portland Maine (by a guy from there). Portland Maine was indeed named because of the nice port there, when they wanted to focus on shipping.
My sister-in-law lives in Beaverton—a suburb of Portland (the Oregon one). It cracks me up when I visit and see the signs. The Beaverton is a satirical publication in Canada. Basically a Canadian version of The Onion.
That would make me want to steal a sign so badly, and I haven’t stolen anything since a pack of gum when I was ten.