Growing up in southern Louisiana, living on the east bank of the Red River in a predominantly African American neighbourhood, Jimmy Donaldson always had a chip on his shoulder towards the people who lived on the west bank. “Growing up, you kind of get pigeonholed into a little box,” he says. “But I would rather be the guy on the block arguing with the guy on the block than the guy sitting on the fence with his head in his hands.” Donaldson was brought up being told that if he wanted something, he had to earn it. As a child, he struggled to make his way in a less affluent area and ended up taking out large loans to further his education. In 2009, he dropped out of high school and went to work for his uncle’s car body shop. From there he started working on racehorses, such as Bubba’s and Slide’s Nascar team. For three years, he worked as the team manager and during that time met Chris Sims, the owner of CHR Racing and a neighbour of his in the garage. Chris, despite having little money, bought himself and his racetrack, Marlin Mills Raceway, a renovated two-mile dirt track in Hammond, Louisiana. Jimmy and Chris were soon inseparable. For two years they owned and raced Bubba and Slide’s Nascar teams together. And that is where the almost 30-year age gap began to hurt. The emotional driving force for a young driver is the age gap, they say. If a car is three decades old, it is the same as it ever was. However, for a new driver, the lack of experience still worries him.
“He also likes to hurt people. When he watches hockey, he brings the sticks to the arena with him. He likes to turn every traffic light red and yellow, because that’s when he thinks of elaborate stunts to get people to hit the car he’s driving like hell.” Sam Brown, his childhood friend, told Cheddar News, “I think people need to realize that he’s not a bad guy. I like him. He’s very funny. He’s just a little prick.” Throughout young adulthood, Donaldson initially struggled to find work, mainly due to his achilles heel: his YouTube videos. In 2016, he partnered with the site Content Creators Unite to put together a coaching program for other creators. “The point is, don’t give up,” he told Curbed at the time. As his career took off and more money rolled in, he contemplated starting a YouTube channel of his own. In 2017, he started The Donaldson Collection, a trailblazing apparel line inspired by The Donaldson Express that champions the motto: “Build it and they will come.” The first store, an online-only spin on the legendary luxury chain’s signature Longford overcoats, was only a imagined dream two years later; the idea was born out of a wake-up moment. One night in 2018, Sam Brown, his childhood pal, came over to his house in Orange County, California, to spend Thanksgiving with his parents — Donaldson had invited them for dinner.
In an effort to tame his channel, Donaldson began posting ad videos to entice viewers. Alongside his trademark morbid sense of humor, his formula generally included enticing, exaggerated knots in his shoelaces; dancing to Slim Shady’s “Lose Yourself” over and over again; or demonstrating how to clean windows using nothing but a broomstick. Throughout peak Donaldson years, his videos accumulated 9.5 million subscribers. Donaldson likely owes thousands of dollars released by YouTube, as well as a share of participating sponsorships, according to a September 2018 Bloomberg Businessweek article. Nonetheless, the reliance on the platform damaged Jimmy Donaldson’s relationship with the real world. As reported by the CBC, a miscarriage and subsequent stillbirth, and the divide he created between himself and his family contributed to his breakup with his second wife. If there ever were a moment to remind us to approach any online activity with extra care and scrutiny, this is it. Soon after his breakup, he moved back to his hometown to pursue a master’s degree in sports journalism. Still, his online persona remained a dark cloud over his already torn-up life.