Pick and roll with Jelly Roll: star plays hoops, encourages inmates at Manitoba Youth Centre
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Hey there, time traveller!
This article was published 19/03/2025 (202 days ago), so information in it may no longer be current.
American rapper and singer Jelly Roll took a break from performing to shoot hoops and speak with incarcerated teens at the Manitoba Youth Centre before his sold-out show in Winnipeg.
A spokesperson for the Manitoba Government and General Employees’ Union, which represents corrections officers at the youth centre, confirmed the Grammy-nominated artist played basketball with each unit at the centre and was “really generous with his time (and) super encouraging.”
The 40-year-old, whose real name is Jason DeFord, took time out during his North American tour and spent three hours signing autographs on clothing and various items youth had on hand and shooting hoops in the courtyard.
DWAYNE LARSON / FREE PRESS American rapper/singer Jelly Roll brought his Beautifully Broken tour to Canada Life Centre Monday evening in WInnipeg to an estimated crowd of 13,500 concert goers.
The country-rap star also commiserated with inmates about making mistakes, but maintained there is always time to turn one’s life around.
“(It was) everything you want to hear from a leader like that,” the spokesperson said Wednesday.
Jelly Roll brought his guitar but did not end up playing any music, the spokesperson said.
He later played a show to about 13,500 fans at the Canada Life Centre in support of his latest studio album, Beautifully Broken.
A mother of an incarcerated youth at the centre said her son got to play ball with the musician and shake his hand.
“(It was) everything you want to hear from a leader like that.”
She was visiting for her son’s court date when she looked out the window and saw Jelly Roll with his entourage.
The star’s management team did not respond to requests for comment before press time.
A Manitoba government spokesperson confirmed it received a request from the artist to visit the youth centre, and “as part of (the province’s) work that helps encourage youth to see positive role models, it was approved.”
Jelly Roll has been making stops at institutions across North America during the tour. The Nashville-born musician has been posting videos to social media of his visits to youth centers and jails, as well as pickup games with community basketball teams.
It began in September 2024 when he posted about a visit to a Salem, Ore. prison on Instagram, showing him singing a cover of Johnny Cash’s Folsom Prison Blues and signing autographs for inmates.
“I am a firm believer that if we commit crimes we should do our time and be held accountable for our actions, but I also believe that every human deserves love no matter how bad of a decision they have made,” Jelly Roll wrote on Instagram.
The artist, who was incarcerated in his youth, has said he wrote his first song while behind bars.
SUPPLIED Briana Knott (left) and Deandra Courchene on their way to the Jelly Roll concert.
Jelly Roll’s generosity continued during his 90-minute set Monday night when he agreed to cover the loans of two University of Manitoba students.
Classmates Briana Knott and Deandra Courchene, who are both studying social work, carried fluorescent signs in the audience with a note asking the star for help.
Jelly Roll announced to the crowd he would agree to pay them if the pair finished their studies.
Before the release of Beautifully Broken, Jelly Roll said he would donate 100 per cent of the profits from his CD and vinyl pre-orders to mental health and addictions charities, including National Alliance on Mental Illness, Shatterproof, Folds of Honor and Wounded Warriors Project.
He began his career as a rapper before becoming an acclaimed country artist. In 2023, he won New Artist of the Year at the Country Music Association Awards.
— with files from The Associated Press
nicole.buffie@freepress.mb.ca

Nicole Buffie
Multimedia producer
Nicole Buffie is a reporter for the Free Press city desk. Born and bred in Winnipeg, Nicole graduated from Red River College’s Creative Communications program in 2020 and worked as a reporter throughout Manitoba before joining the Free Press newsroom as a multimedia producer in 2023. Read more about Nicole.
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