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After the sacking of Andy King, former England international "Razor" was brought to the club in August 2001 as a player/coach with new boss Roy Evans - his first venture into a coaching role after gaining an FA coaching badge.
Originally a great crowd favourite, Ruddock made his debut for the club on 1st September, after a bizarre episode with the club's kit manufacturers, who for a time seemed unable to produce a pair of shorts big enough for Ruddock's ample frame. It was worth the wait - Ruddock scoring a thunderous free-kick to give the Town a 1-0 win over Colchester.
During his playing career at Swindon, Ruddock brought great character and experience to the team, though very little pace. This playing career was short-lived, however - as things started to go wrong between Ruddock and the club when the chairman who brought him to the County Ground, Danny Donegan, was ousted, and Roy Evans followed him out of the exit door.
Between Evans leaving and Andy King's reinstatement, on 21st December, Ruddock was sent-off in a 3-1 defeat at Notts County. It proved to be his last game for the club, injury keeping him out for the rest of the season. It was during this time that the new board of directors began to question the validity of Ruddock's contract - believed to be around £5,000 per week.
With the club in real financial difficulties, the board began High Court proceedings to retrieve the money from the previous administration, arguing that the deal was not in the best interests of the club. When the argument went on into the following season, the situation became worse when Ruddock was advised to quit the game by a specialist (which he refused to do), and Ruddock had his coaching duties taken away when Steve Coppell joined the club as a temporary assistant manager. The whole affair became very messy - with both the club and Ruddock choosing to argue their points through the media. When the anniversary of Ruddock's arrival came, it triggered a "loyalty bonus" of £57,000, and the board decided to stop paying Ruddock's wages in an attempt to force him out of the club.
Whilst the club made repeated offers to Ruddock for him to leave, it appeared as though he was unwilling to compromise, especially as he still had two years remaining on his contract. Predictably, Ruddock took the club to an industrial tribunal to recover his unpaid salary, before an 12th hour deal was struck, which saw Ruddock's contract terminated as of 31st December 2002, in return for a payment believed to be in the region of £200,000.
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