Theo Jones is the brother of Simon Jones (who changed his name to Milo Entwistle after a fatal car accident in February 2004). Theo paid Milo a visit in April 2018, demanding that Milo gave him £200 or else he would reveal to the Cunningham family that Milo was the driver of the van that crashed into Helen and Gordon Cunningham's car and killed them. Theo later met Cindy Cunningham at Esther's Magic Bean and flirted with her, later sleeping with her despite Milo paying Theo the blackmail money.
Theo began playing with fire by telling Cindy that Milo was his brother and changed his name from 'Simon' to Milo. Milo crashed Cindy and Theo's date at The Hutch and sabotaged the date by claiming that Theo caught an STD during an affair, causing her to quickly leave. A furious Theo told Milo that if he did not receive regular payments, he would return and reveal all about the crash to Cindy.
A few weeks later, Theo turned up at 65 Christleton Terrace to blackmail Milo again. Cindy and her daughter Holly Cunningham were both left smitten, with Theo telling Cindy that what Milo said about the affair was untrue. Theo taunted Milo, blaming him for their family troubles: their mother dying of cancer a few years after Milo's imprisonment and their father developing liver cirrhosis due to alcoholism. Milo gave Theo all of the money he had in his wallet but Cindy convinced him to remain in Chester.
Realising that he could not evict Theo from the village, Milo set up a paint can trap to kill Theo, but Dirk Savage accidentally set it off. Milo ended up telling Dirk the truth about Gordon and Helen's deaths and the blackmail. Dirk grabbed Theo, revealing that he knew about the crash, threatening to kill Theo if he ever saw him again.