With a damp shirt draped around his neck and his face shaded against the hot morning sun by the brim of a red “Make America Great Again” cap, Sean MacCaskill hawked his wares to the Trump supporters gathered outside Portland City Hall, while nearby police officers struggled to contain a woman shouting that his would-be clients were racists.
It’s nothing new for MacCaskill. He’s been selling Trump t-shirts and hats since the billionaire real estate mogul accepted the Republican nomination for the presidency in Cleveland, the 24-year-old merchant’s home town. And before that he sold political swag during the 2008 presidential election, crossing the aisle with gear for both Barack Obama and Mitt Romney supporters. He’s also worked at Hillary Clinton and Bernie Sanders events.
For MacCaskill, the success of a political campaign stop is measured in t-shirts sold. On a good day, he, his cousin and the two other guys who work with them will move close to 400 shirts and caps at $20 a piece.
But around 1 pm with most Trump supporters already inside Merrill Auditorium, MacCaskill was ready to call left-leaning Portland a flop.
“It hasn’t been good at all today,” MacCaskill said “We’re probably only going to move like 50 shirts today.”
Plus, as he does at every Trump rally, MacCaskill has to contend with the anti-Trump demonstrators who demand to know why he, as a black man, would support a candidate that they see as racist.
Earlier in the day a woman approached one of MacCaskill’s fellow merchants, also black, and said that what he was doing was akin to supporting Hitler. History would judge, she admonished, before stalking off.
But MacCaskill said that wearing the Trump hat is just a way of promoting his goods. He’s personally undecided as to who to vote for and has learned to let people’s anger slide off him.
“I think this campaign is dividing us for real. You know, black and white, right and wrong,” he said. “But at the end of the day this is supply and demand.”
The divide he sees most is between rich and poor. In Portland, and at most campaign stops, he sells his shirts for $20. But at the Republican National Convention and at other events where he expects a more well-heeled crowd, he’ll raise the price a bit.
He understands the appeal of a rich candidate who is promising greatness to working class people around the country, he said.
“I’m trying to get rich. He’s already rich,” MacCaskill said, and then snapped back into work.
“Shirts all sizes. Shirts all sizes,” he yelled.
Correction: A previous version of this post misstated the name of the venue where Trump spoke. It was Merrill Auditorium.