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He played on the left wing and was the son of Stuart Naysmith. He joined Harchester United after being released from Birmingham City due to committing arson. He was offered a trial and impressed manager Patrick Doyle. In his first season at the club, he had several off the field troubles such as a police investigation into a hit and run, and was injured in a fight by Marcel Sabatier that meant he missed the rest of the season.
Ryan started the 2003-04 season with a bang, playing well supplying Luke Davenport up front and gaining a call to the England squad. Ryan, though had accidentally killed a ticket tout during a fight, and the guilt consumed him, and when a bid come in from Liverpool for £11 million, he took the move, and when Luke Davenport blocked it, Ryan punched him, causing serious eye trauma (blind in one eye). Afterwards, Ryan checked into a clinic for depression. He returned in the February when the club was wound up, and the players played without any money and played well for the rest of the season, it turned out though in the penultimate game of the season against Wolves, he had been taking Nandrolone after drugs testers turned up and asked to be taken off at half time. To make matters worse, his father Stuart entered the witness protection scheme after giving evidence in the case of Sabatier's steroid abuse-related death. Ryan managed to gain a call up for England's Euro 2004 campaign, but broke his leg in training.
Ryan missed most of the 2004-05 season with injury, and with nothing to do, found himself to be having an affair with Chelsea Wright, wife of goalkeeper, Vivian 'Jaws' Wright. When she left town, Viv found out she had left, he went looking for the culprit and when he turned up on Ryan's doorstep with a shotgun, Ryan blamed Clyde who had committed suicide, making up a story to save himself. Ryan returned to the team in the March, and helped lead the team into the Championship promotion play-offs. On the eve of the play-off final, Viv read a letter penned by Barker revealing the truth about Chelsea's affair. When Viv went to confront Ryan in the Millennium Stadium car park before the game, Ryan escaped in Barker's car. Viv called Ryan as he wanted him to play in the match, Ryan agreed, but on his way back to the ground was arrested for reckless driving and the police found Fletch's body in the boot and arrested him. This proved lucky for Ryan as he was not on the coach when Barker crashed his car into it, killing everyone on board, including Viv in the resulting explosion.
The following season, Ryan struggled to come to terms with the loss of all his mates, and was dubbed 'Lucky' by Casper Rose. It took a while to regain his form and confidence, but it soon returned, and on the night of the Christmas party, he slept with Cindi Marshall, not knowing she was Gavin Moody's girlfriend. On Gavin's stag trip, Ryan confesses to Gavin, but Gavin is upset and shoots dead Ryan's beloved pet dog, Jaws, sparking a feud between the two players which spills out onto the pitch in the FA Cup quarter final game, getting both players sent off. Ryan is banned for the replay, and at his lowest point goes up to the top of the stadium where Clyde killed himself and thinks about jumping before getting stopped. He left the club for Villarreal CF after punching Gavin as part of a match fixing scandal. He later reappeared on the final day of the season 2006-07 as a TV pundit, where Harchester won the Premier League after beating Chelsea 2-1, but the fate of the team, stadium, fans and Ryan himself was left ambiguous as a stand was set on fire after a cigarette was dropped into petrol left from Ex-Captain Danny Sullivan's planned revenge on the club.