Crockett, a middle-aged man with a tuft of thick brown hair who speaks slowly due to complications with multiple sclerosis, was desperate. He told the President that despite his illness, he had been turned down four times for Social Security benefits and he asked Obama for help.
"Is there anything you can do?" Crockett pleaded.
Obama promised to look into it. Then, in a moment that would overshadow much of the media coverage of his trip, Obama broke into song, crooning, "The Ballad of Davy Crockett."
"Y'all remember that TV show?" he said.
Most of the stories written about the encounter focused on how the President sang a funny song to a man with a famous name, but Crockett's plight was largely forgotten.
At the time, Crockett was struggling with little hope in sight. His father had recently died. He was unable to work due to the illness and he had lost his family's land and childhood home due to foreclosure, forcing him to live in a horse trailer owned by a family friend.
More than a year later, CNN returned to Bulls Gap, a small, picturesque town surrounded by rolling green hills and farmland in the northeast corner of this deep red Tennessee.
"I didn't think Obama would help me," Crockett, who claims to have ancestral ties with the famous 19th century congressman, said. "He's the President of the United States."
Two weeks after his meeting with Obama, Crockett said, he received a letter from the Social Security Administration. After months of of being turned down for benefits, his requests had finally been approved. Obama had come through.
Crockett, who walks with the help of a cane and continues to fight the increasing symptoms of his disease, has moved out of the horse trailer and into an apartment in nearby Greeneville. He occasionally works with a day program for people with disabilities, which has helped keep him busy since he left his job in a factory building bombs for the military.
For the past year, he has followed the presidential race closely. But politically, Crockett, whose county overwhelmingly supported Mitt Romney over Obama in 2012, is in the minority. He plans to support Democratic nominee Hillary Clinton. As a man with a disability, Crockett took notice last November when Republican nominee Donald Trump appeared to mock a journalist at a rally who suffers from a bone disease the restricts the use of his joints. The video of Trump's theatrical mimicking of the reporter, which a pro-Clinton super PAC used in an ad this year, infuriated Crockett.
"I was mad," Crockett said. "Donald makes fun of people that have the stuff like I have, I said to myself, I said, 'I don't want to vote for this man and I said I hope Hillary gets it.'"
Crockett said that even though he was able to meet one president, he probably won't have another chance in the future. But if he met Trump, he said, the meeting probably wouldn't be as cordial.
"If I got to meet Donald Trump I would say, what makes you think that you should deserve to be president? I'd say, I have MS, and you're going to make fun of people that have a disease and sickness? What in the world is wrong with you?"