After 19 years behind bars, Jesse Crosson opens up about what life is like in prison.
In 2002, Crosson was originally sentenced to 32 years in prison, just as he turned 18, after committing two separate and unrelated crimes: being caught in the act of robbery and a shooting.
Now a free man, 38-year-old Crosson shares his prison stories to his 1.2 million TikTok followers who reveal the fascinating facts about what life is really like in prison – and what it was like adjusting to life outside when he was released.
In a recent clip, the former inmate said the moment he was released from prison “felt like a dream.”
After 19 years behind bars, Jesse Crosson (pictured) shares insight into what life in prison is like via TikTok
In 2002, Crosson was originally sentenced to 32 years in prison, just as he turned 18, after committing two separate and unrelated crimes; getting caught in a robbery and shooting
He recalled walking outside for the first time and it felt “awkward and weird” to get into a car — and he even had a “breakdown” in Costco after shopping with his newfound freedom.
“I started to feel two things,” he recalled. “One was a feeling of sadness for everything I lost and I began to realize that all those years had passed, and the other was a feeling of joy.”
Crosson, who lives in Charlottesville, Virginia, recalled changing his mindset from living as a free man, “like a dream,” to “waking up” from a bad dream.
“It was back to reality for the first time,” said the ex-prisoner explained. “And it was where I belonged.”
The motivational speaker, who founded the Second Chancer Foundation in 2022 to provide direct services to prisoners, admitted that he suffered from a breakdown and PTSD, and struggled in different environments and relationships.
Crosson also remembers the moment he found out he was being released from prison – he said it had been a “surprise” – and waking up that day to think he still had 10 years left in prison.
However, he was called to the counselor's office, who told him the good news: he was a free man.
After being given “ridiculous” release clothes – oversized khaki pants and a large khaki shirt – he left the prison and was picked up by his mother, whom he was finally able to hug after spending 15 minutes filling out the final paperwork .
Crosson admitted that he had an aversion to clothes after he got out of prison because he was arrested in them
In one video, Crosson also recalls the moment he found out he was being released from prison, saying it was a “surprise”
Crosson, pictured in an undisclosed year's jail, was sentenced to double the recommended sentence
“I picked her up and started swinging her around,” he remembers.
In a TikTok posted in June, Crosson explained that he was arrested after he and his co-defendants ran out of money and tried to find a solution: He made the decision to rob the home of a restaurant owner someone had worked for.
Although they justified the crime by convincing themselves, the restaurant owners were not good people.
However, someone came home and it turned into a home invasion, leaving Crosson paranoid and worried that they were after him.
Wanting to defend himself, Crosson bought a gun from a friend – which turned out to be stolen – and was involved in a fight that ended in a chase during which he fired his gun.
He was arrested and sentenced to 32 years, double the recommended sentence.
“When I was arrested, I looked completely insane,” the ex-criminal recalled, saying he dressed like a gangster, inspired by his friend's uncle, who rightly was one.
'I had these walking shoes on, but I had dress socks, I didn't have boxers on because we are so tense, we can never organize ourselves to do laundry, but I wore dress clothes, (I) wanted to be just like him ', he said.
'I also had a long overcoat that my stepfather had given me and besides it making me look like a gangster, we had a strap on the AK so I could put it over my shoulder with a regular clip in it, that wasn't possible. even that it was under the jacket,” he added.
Crosson founded the Second Chancer Foundation last year to provide direct services to inmates
The ex-con was sentenced to 32 years in prison in 2002, but was released after 19 years
The free man said he was arrested in that outfit and had to wear it again when he was transferred from prison to the halfway house before beginning his sentence.
While he was being processed, he was given the choice to send the garments home or leave them there. Instead, he chose to throw the clothes away.
“With the limited money on the books, there was no way I was going to pay the shipping costs (when) I could buy food and hygiene instead,” he explained.
'Maybe that's why I was so reluctant to wear formal clothes again, because for about a year and a half to almost two years I only wore T-shirts and jeans. I thought, no, I don't need that fancy stuff,” he added thoughtfully.
In other videos, Crosson revealed more information about his time in prison, including his unusual mentor, who turned out to be a serial killer.
“I was surprised because I said you know I really like this guy,” he recalled in a clip on TikTok. 'I get along well with him, he teaches me something every day, he has helped me a lot to see the world in a different way.'
Although Crosson appears to regret his actions, he does not regret his arrest.
“I had to be arrested,” he said in a video explaining why he was put behind bars. “I was an active threat to other people.”
“In many ways, my arrest, being taken out of the crazy lifestyle, turning the tail I was in, saved my life,” he added sincerely.
Crosson also said that with “great love and support” he was able to get his life back on track in prison.
“I mentored other men, earned a bachelor's degree, became an electrician, wrote articles for publication and found a path forward,” he said.