Jason was first imprisoned in about 2011, just after his then girlfriend had given birth to his child. By 2017, Jason's former girlfriend was in New Zealand with their child and Jason was behind bars again. The years behind bars had changed Jason and he turned into a bully and drug dealer.
In February 2017, Jason was introduced to Aaron Dingle on the first day of his twelve-month sentence for GBH. Jason was impressed that Aaron was a Dingle and asked about Cain Dingle. Jason directed homophobic abuse towards a gay prisoner and was annoyed when Aaron stuck up for him. Jason soon realised Aaron was gay after witnessing Aaron's boyfriend Robert Sugden touch Aaron's knee during a visit. At visiting a few days later, Jason made a comment to Aaron's mother Chas Dingle about her son being gay, so Chas warned him to stay away from her boy. Later that day Aaron and Jason fought. Jason became suspicious when a prisoner named Barry, who had know Aaron from a previous stint behind bars, called Aaron 'Livesy'. Jason put two and two together and worked out Aaron was the son of former inmate, peadophile Gordon Livesy. Jason visited Aaron in his cell and insisted he should be thanking him as he got inside Gordon's head and drove him to suicide. Jason wound Aaron up so Aaron lashed out and punched him. Jason didn't punch him back immediately, but instead returned to Aaron's cell later in the day mob handed and beat Aaron to a pulp. A few days later, Jason threw Aaron in a cell and tortured him by telling him that they were in Gordon's old cell where he hung himself. To cope with the pain of the beatings, Aaron's cellmate Ethan offered him a drug named Spice and Aaron was soon desperate for more. Ethan explained he couldn't get him more and revealed Jason was the only dealer on the wing. Jason handed over some drugs on condition that Aaron did some jobs for him and Aaron agreed. Jason gave Aaron the most risky job, delivering the drugs to fellow prisoners.
In July, Aaron called Ethan to buy spice, but Jason went with him, causing trouble for Aaron. Cain came to Aaron's rescue when Jason threatened Aaron with a knife. In August, Aaron went to his uncle Zak's old gym and ran into Jason, with his friends Adam and Victoria Barton. Jason harassed Aaron and after Adam told him to leave, Adam is beaten up.
Aaron confronted Jason over beating up Adam and Jason challenged Aaron into a match. Robert attempted to pay Jason off but Jason refused to call off the fight. The next day, Aaron and Jason fought in the ring as Aaron stood up to Jason and telling him what he thought of him before walking away. Later, Jason arrived at Aaron's house where Aaron attacked him before throwing him out. A drunk Jason headed back to The Mill and was about to throw a bottle into the window until Cain stepped in to stop him before punching him. The next day, Aaron went on a run where he found Jason beaten up in the graveyard and took him to his house, where he had it out with Jason. A taxi arrives for Jason and they have their last conversation before Jason leaves the village.