Premier League soccer boss Tony Pulis has lost a £3.7 million High Court fight with former club Crystal Palace.
Pulis, who now manages West Bromwich Albion, had earlier this year been ordered to pay the amount in damages by a Premier League Managers' Arbitration Tribunal.
He had claimed that the decision was unfair and mounted a challenge in the High Court in London but judge Michael Burton has ruled against him.
Burton said the tribunal had analysed evidence after Palace bosses complained about the way Pulis had left the club at the start of the 2014-15 season.
He said Pulis had a contract which would see him get a £2 million bonus if he kept Palace in the Premier League in 2013-14 and stayed in the manager's job until 31 August 2014.
Pulis had kept Palace in the top flight but had not stayed until 31 August 2014.
Palace bosses had complained that Pulis had deceived them into paying the bonus early by saying he was "committed" to the club and "urgently needed the money early" so that he could buy some land for his children.
Burton said Palace bosses had agreed to Pulis's request for early payment and handed over the £2 million on 12 August 2014.
He said that on 13 August, Pulis told bosses he wanted to leave, and on 14 August he left.
Pulis had denied "fraud" and insisted he only wanted to leave if it was "mutually agreeable for him to leave on the eve of the new season", and that it had been "mutually agreeable".
Arbitrators had concluded that Pulis made "false representations", decided he had not been "committed to the club", had not intended to stay until 31 August and "there was no such land transaction".
They also concluded that he had not told the truth and "deliberately misled" Palace chairman Steve Parish "concerning his intentions".
"Mr Pulis secured early payment of his bonus from the club by deceit in August 2014," arbitrators concluded.
"The day after he had secured payment of £2 million ... he dropped the bombshell on the club that he intended to leave, leaving it, as must have been his intention, in the lurch on the eve of the new season."
Arbitrators added: "By any standards his conduct (prior to and during the litigation) has been shown to be disgraceful."
Burton said the arbitration tribunal was made up of three senior barristers, which heard evidence behind closed doors.
The judge said he had analysed Pulis's complaints about the arbitrators' decisions and concluded that his challenge should be dismissed and that he would enforce the damages awarded by the arbitrators.
Burton said he had also analysed Pulis's challenge at a private hearing - in line with judges' normal policy. But Burton said he thought it appropriate that his ruling should be made public.
