Anthony Constantino is not the candidate local Republican Party officials would have picked in New York’s far-upstate 21st District. The owner of the merch-production company Sticker Mule loves Donald Trump — a prerequisite for the House GOP today — but is untested on the campaign trail. Four years ago, Constantino made his pro debut as a welterweight boxer in Mexico City, winning his first fight after entering the sport at the age of 40. “There’s a criticism of people successful in the business world that they get lucky, and there’s more admiration for boxers,” he tells me. “So I was like, Well, if I can be good at this too, maybe it’s not luck.” He’s not as polished as most elder millennials running for Congress, speaking hurriedly and favoring tight ripped jeans in many of his campaign videos. He says that when Roger Stone, an early and unofficial adviser, first saw them, he asked, “Are you trying to fucking lose?”

“It’s the biggest ongoing fight that we have,” Stone tells me. “I just want him to dress like a congressman.”

Another indicator of Constantino’s outsider status is the unusual company he keeps. Two weeks before the primary, I spoke with Constantino at a golf-course country club he rented out about ten miles south of Lake George. We peeled away from the small crowd to talk in an empty ballroom — followed by a campaign volunteer wearing black Asics with striped black socks, camo shorts, a black sleeveless compression shirt, and a brown-and-beige fedora who caught the interview on-camera. That day, I also ran into Sticker Mule’s marketing guru, a man who goes by Greatness. He is easy to find. Greatness usually wears a Sticker Mule gold chain and has two tattoos on his face that say “Greatness.”

Over the past few months, Greatness has been promoting Sticker Mule with a viral campaign in which he goes to cities across the country, rubs baby oil all over a watermelon, and then throws it in the air for a contestant to catch. If they don’t drop it, they get a few hundred dollars. “I’m in the hood near you throwing watermelons!” he raps in a song about the challenge. Greatness, who is from Tampa, has been promoting the Constantino campaign in videos online. But he says he is in upstate New York in an unofficial capacity to give him “positive encouragement as a friend.”

Constantino and Greatness met on Instagram and first linked last year to record a rap album in Florida called Thank You President Trump. It was recorded when Zohran Mamdani was running for New York City mayor, and they saw an opportunity for a topical diss track. “Mamdani is running in an urban community where people listen to rap,” Constantino says, hoping that he could educate “people about those topics.” Throughout the song, which made it onto WorldstarHipHop, he accuses the city’s first Muslim mayor of being a terrorist: “Terrorists aren’t flying planes into buildings anymore, they’re coming at us different.”

The local GOP might not love these extracurriculars from a candidate running in the district to replace Elise Stefanik, the third-ranking House Republican from 2021 until 2025, who announced she would not seek reelection in the 24 red seat. But they aren’t making the election-defining endorsements in the party today. President Donald Trump is. So far this year, every one of his 155 House endorsements have won their primary. And thanks to Constantino’s loud support of the president, he won Trump’s co-sign in April.

Constantino wasn’t all that focused on politics until the president was shot in the ear on July 13,........

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