Derek Milligan was a businessman in debt to loan shark Gary Windass.
In August 2019, Gary enlisted Derek's help in order to help him infiltrate the construction of Underworld - which was being repaired from the roof collapse in March having been sabotaged by Gary, killing local woman Rana Habeeb in the process. Derek met with factory owner Nick Tilsley posing as a contractor and offered to buy the factory site, rebuild the property and then lease the building out to him. Ultimately Nick agreed to Derek's low offer of £10,000 for the land - despite the rebuild being estimated at £100,000 - as he wanted to ensure that his workers move out of the Community Centre and back into a proper workplace. However, Gary's involvement caused Sarah Platt some concern and she attempted to rally the workers against Nick's decision - although, she was outvoted when the workers agreed with Nick. With everything going to plan, Gary ordered Derek to make Nick deal with him in the future - explaining that he had paid off his debts and that Derek was no longer needed on the street. Frustratingly, Nick revealed that he'd prefer to deal with Derek instead of Gary - leaving Derek with a sense of control over the loan shark.
When Sarah and her boyfriend Adam Barlow invited Derek for a drink at the Rovers Return to get acquainted, he accepted - infuriating Gary. Later, Gary attempted to reassert his dominance but Derek was left unmoved having seen how another of Gary's debtors, Ryan Connor, had easily been able to get around him. To this Gary shoved Derek against a wall in the men's toilets, threatening him with violence - but the pair were forced to play down the confrontation when Adam walked in. The following month, Derek took a shine to factory worker Izzy Armstrong - unaware that she was also Gary's ex-girlfriend and mother to his son Jake. At the same time, Nick pushed Derek to sign a rental agreement for the refurbished factory complete with a short-term discount - behind Gary's back.
When Gary returned he was taken aback to discover that Derek had signed the document without his acknowledgement, and was furious to walk in on Derek and Izzy's date at Speed Daal. Believing Derek's actions to be malicious, Gary once again confronted him - but Derek simply pointed out that he still hadn't dealt with Ryan and therefore he wasn't threatened by him. Derek later considered calling off his budding relationship with Izzy, insisting that it wouldn't be fair on Gary - but Izzy reminded him that he was Gary's boss and could therefore do as he pleased. Eventually, Derek and Izzy spent the night together - forcing Gary to take extreme action against Ryan. When Derek learnt that Ryan had been "mugged" he realised that Gary had actually given him a severe beating and, as Gary hinted that the same would happen to him if he didn't follow his orders, Derek called things off with Izzy before fleeing the street in fear.
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