Roy Shaw (left) counts Great Train Robber Ronnie Biggs among his friends
Champion bare-knuckle fighter and underworld figure Roy 'Pretty Boy' Shaw has been awarded almost £1m after a court battle with a former friend.
Linda Finnimore, 43, claimed the former villain, 73, had paid her £643,000 for her part in a £2.6m land sale at a time when she was managing his affairs.
But Mr Shaw, a friend of the notorious Kray twins, said she had taken him "for a right mug" in transferring the cash.
High Court judge Sir John Lindsay said she had been "untruthful" in evidence.
He said both characters were part of a "criminal milieu... of villains and gangsters" who had become close after meeting in Spain.
The judge acknowledged Mr Shaw's history of criminal violence and dishonesty, pointing out that by 1974 he had spent around 18 years in prison.
Mr Shaw then enjoyed a successful career from unlicensed bare-knuckle boxing and lived an extravagant lifestyle.
He was still well-known in the "raffish" worlds of villains to the extent gangster Ronnie Kray's widow Kate had published his biography, said Judge Lindsay.
Of Miss Finnimore, the judge said: "She, for whom the word 'feisty' could have been minted, is more educated than he and far more intelligent.
"Unfortunately, her considerable skills have not always been applied to acceptable purposes."
At one time Miss Finnimore called herself Linda Kray, claiming to be a daughter of Reggie Kray.
Mr Shaw liked to "show her off as a girlfriend" and trusted her with his business affairs, the judge said.
However, he dismissed Miss Finnimore's claims that Mr Shaw had promised a share of the proceeds from the sale of land at Chadwell Heath, north-east London.
The judge ruled there was no such verbal contract and ordered Miss Finnimore to repay the money, together with sums of £208,450, £20,000 and £57,000, plus interest.
He said that when it was put to Mr Shaw in court that he intended to transfer £643,000 to her, he replied: "Don't talk so silly - she took me for a right mug."