I'll open this up for any sport not just football.
My choice would be celebrity fat c*nt Neil Ruddock
Here's why from a 2002 article in the independent.
Quote:
The wages dispute between Neil Ruddock and Swindon Town took a new twist yesterday after the former Liverpool defender succeeded in freezing the club's share of an FA Cup gate.
Ruddock, who claims he is owed £86,000 by the Second Division club, obtained a High Court order to block their £140,000 share of last Sunday's second round-tie at Oxford United. Swindon insist they have no money to pay Ruddock, and the two parties will meet at an industrial tribunal today.
Since signing for Swindon as player-coach in August 2001, the veteran centre-half has played 17 games, his last appearance being last December. His contract, which still has another 18 months to run, is believed to be worth £5,000 per-week, and accounts for 25 per-cent of Swindon's total wage bill.
The club's majority shareholder had agreed to fund a pay-off for Ruddock, who turned down the amount on offer. The 18-month remainder of his contract, plus the amount he claims he is owed, would total around £426,000.
A knee injury has prevented Ruddock from playing and affected his struggle for fitness. Last season, Swindon had to commission their Far Eastern kit manufacturer to make specially large shorts for Ruddock, who tried on 86 pairs at the club and was unable to find a pair that fit him.
Swindon's chief executive Mark Devlin said: "We cannot pay him because the money does not exist within the club. We have said all along that any settlement with Neil Ruddock was going to have to be met by a third party and that has always been the case."
Ruddock's solicitor Stephen Welfare claimed money owed to the player could be paid out of what had been frozen. Welfare said: "The club has always said that the basic wages of its players are budgeted for. They also said before the FA cup match that this was an unbudgeted for windfall, which says it all really."
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The club went into administration shortly afterwards.