He traveled from rally to rally with his guitar in tow, crooning pro-Donald Trump tunes and hailing the then Republican candidate as the answer to the US heroin epidemic that took his son's life.
Though his songs earned him the moniker "the Trump troubadour," these days Kraig Moss has stopped singing for the president: the US leader's push for a health bill that would have restricted access to opioid addiction treatment for thousands of people left the 58-year-old mired in doubt.
When Moss strums his guitar now, it's to sing sorrowful ballads in memory of his son Rob, who died of a heroin overdose in 2014 at the age of 24.
Trump "is the one that pioneered the idea that we have a heroin epidemic in this country," Moss said. "I feel on that subject very let down -- because that's what drove me in order to want to do everything I did; make all of the sacrifices I did to follow him around."
Moss had stopped making mortgage payments so he could trail the Trump campaign; now he is about to leave his house in the small upstate New York town of Owego for a mobile home.
But he said he has no regrets: "I'm not ashamed of what I did, mostly because I know I've gotten at least one person, one young adult to stand up at a party and probably say, 'You know what? That stuff kills -- I'm out of here."
"I know there's young adults that have that attitude now because of the talks that we have had."
Despite his disappointment in the first two months of Trump's tenure, Moss said he thinks the president "still has potential."
"He's got to come down to real life and... remember the little people who got him into office," Moss said.
But the former construction worker wonders what Trump -- who cast himself as a hardline dealmaker who alone could uplift America -- can really get done from the White House.
"I'm concerned that the same complications that presented itself through health care will present themselves with the immigration and the same complications might arise with his business plans."
The Republican bid to repeal and replace former president Barack Obama's signature health care law ended in crushing defeat, after dissent within Trump's own party stymied his efforts.
It is too early to tell whether Republicans will launch another fight to kill Obamacare.
Meanwhile Moss, who has been separated for years, finds himself alone mourning his child's death. His house is nearly empty -- save for the living room, which is littered with piles of photos and t-shirts bearing the likeness of his son, three years after the young man's death.
After the campaign catapulted him into the public eye, Moss began receiving contributions from people nationwide to pay for a memorial stone -- but he does not yet have the heart to get one.
Moss said following the Trump campaign granted him a way to keep his son alive.
"I did not realize it until these people just offered to pay" for the memorial, he said. "It's like, that is a final closure."
"I don't know if I am ready for that."