In April 1967, Gregg was stationed in Burtonwood along with his friend Gary Strauss. He made his way to Weatherfield where he met old flame Dot Greenhalgh who was hysterical to see him again. In May, Dot and Gregg successfully persuaded soldier Steve Tanner and Elsie Tanner to start dating. In September, Gregg served as the best man at Steve and Elsie's wedding.
Gregg returned to Weatherfield in September 1968 and was disappointed to find out that Steve and Elsie's relationship had ended. At the end of the month, Gregg was told that Steve had been pushed down a flight of stairs and had died. Despite his friend's death, Gregg didn't appear bothered about it which surprised Dot. Later on the police saw Gregg about the murder and Gregg told them that he was with a woman called Sally Wells in Altrincham. Dot was shocked when she heard that Gregg had been with another woman and decided to break up with Gregg.
In 1970, Gregg and Gary were sent back to Weatherfield by Major Ryan to hunt down soldier Joe Donelli who had gone AWOL. The pair found out that Joe had no plans to return to the military and it emerged that two years earlier it was he who murdered Steve Tanner following a row over gambling debts. Joe realised that they were onto him and so Joe held Minnie Caldwell and Stan Ogden hostage at 5 Coronation Street. Gregg called the police and eventually they surrounded the house. In the end Joe killed himself, ending the siege. After the siege Gregg and Gary held a farewell party with all the drinks on them and left Weatherfield for good.
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