The Real Reason Jelly Roll Was Arrested At 13

Jelly Roll may be living a lavish life now, but his success did not come easily. The heavily tattooed crooner has a criminal record almost as long as his music catalog with 40 arrests to his name. "There was a time in my life where I truly thought... this was it," he admitted on "CBS News Sunday Morning" in January 2024, while visiting his old jail cell at the Metro-Davidson County Detention Facility in Nashville. But fortunately, the country star was one of the lucky ones. While Jelly Roll's real life story is tragic, he was able to make a complete transformation from felon into a music superstar. Who would have thought that little Jason Bradley DeFord, first arrested at the tender age of 13, would one day be topping the charts?

Jelly Roll's first arrest marked the beginning of a decade-long string of incarcerations. But how did it all start? What led him down this path in the first place? The singer detailed his first felony in a 2024 appearance on the "On Purpose with Jay Shetty" podcast, confirming that he was arrested for strong-arm robbery, aka a robbery where there isn't a deadly weapon involved. The "Save Me" hitmaker confessed that he had "deep-rooted insecurities" as a kid because of his size, which prompted him to act out. "I'd gotten a fight with a kid and back then they had the chain wallets [...] I grabbed a chain wallet to try to hit him with it," Jelly Roll recounted, noting that he ultimately got "20-something months" for this offense. 

There are many tragic details about Jelly Roll's childhood and while there isn't one clear answer as to what set the country singer on a path of crime, the year he was first handcuffed by police notably coincided with another major life event: His parents' divorce. Jelly Roll wanted to help his mom, who struggled with both mental health problems and substance abuse, so he decided to live with her, which the "All My Life" hitmaker now realizes may not have been the wisest choice. As he informed Billboard in June 2023: "I told my dad before he died [in 2019], 'I wonder, if I'd have moved in with you when you divorced, if I'd have went to Vanderbilt [University] or something.'"

At such a young age, Jelly Roll had to find ways to bring in money to support them both, which led him to sell drugs. Heavy drug use and getting by on side hustles were common in his hometown of Antioch, Tennessee. "I want to be open about it — I thought it was my only choice. I lived in a decently middle-class neighborhood, but I didn't know one person on my street with a career. Everybody did drugs," he told the New York Times in 2024. The singer later added: "The most obvious way to make money was what was happening in the neighborhood.” Although Jelly Roll's first arrest wasn't drug-related, many of his later charges stemmed from dealing and possession.