Well, I never…
Doesn’t answer the question of “Why are these tourists only interested in buying extremely pr-Trump shirts?” In your scenario, there ought to be lots of anti-Trump or pro-Democrat buyers, too. My question still stands, unanswered – why are there so many VERY Pro-Trump shirts or sale, and no other political viewpoint?
Another WAG: outside of college towns and other strongly liberal areas (such as Boston, mentioned in your OP), there probably isn’t as much of a market for shirts with in-your-face liberal messaging on them.
But, about 40% of Americans seem to be really, REALLY in love with Trump (based on the fact that that seems to be the “floor” on his approval ratings), and a substantial number of them seem to be the sort who eagerly advertise their political views on their bumper stickers, on their Facebook pages…and in the shirts and hats they like to wear.
I simply suspect that, in any given tourist area, there’s just a lot more people who will eagerly buy a pro-Trump shirt than an anti-Trump shirt.
No I haven’t seen any pro-Trump T-shirts in Chicago, but I have heard that Streeterville is MAGA Country…
…No, wait…
He’s popular with bikers? After he screwed over Harley-Davidson?
Who buys over-priced garbage in tourist traps? Rubes and suckers.