KIRK: I got the idea when I read about something a man was doing in Portland.
LORELAI: What was he doing?
KIRK: He was printing daily T-shirts featuring a humorous topical headline of something he witnessed around town.
Portland, a port city and the largest city in Oregon, in the Pacific North West of the US. It has a population of around 600 000. Named after Portland in Maine, the settlement began to be populated in the 1840s, as it was near the end of the Oregon Trail which led wagon trains to the west. Beginning in the 1960s, Portland became noted for its growing liberal and progressive political values, earning it a reputation as a hip bastion of counterculture.
I have been unable to discover if the man in Portland with the tee shirt business was real, or fictional. I have found no trace of him, and suspect he may be the writer’s idea of something quirky that people in Portland might do.
The Annotated Gilmore Girls 