A "thug" and "bully" who police said preyed on vulnerable people for fun is starting a five and a half year jail sentence.
John Damon Gizzi, a millionaire builder from St Asaph, was caught for one attack after a listening device was installed in his Bentley.
Gizzi, 34, previously admitted two charges of grievous bodily harm and one of actual bodily harm.
He beat up two homeless men with wooden staves, Chester Crown Court heard.
He also admitted conspiracy to sell contraband cigarettes and customs and excise tax evasion worth up to £750,000.
Twenty two offences of mortgage fraud totalling £1.4m were also taken into consideration.
Appearing at Chester Crown Court last week, co-accused Dennis Fontenot, 32, from Liverpool, also pleaded guilty to causing grevious bodily harm with intent and conspiracy to sell counterfeit cigarettes.
On Friday, he was sentenced to 18 months.
Simon Medland, prosecuting, told of an assault on a homeless man, at a boarded up cafe, owned by Gizzi, in Rhyl.
He said: "It was fairly well known that people from the streets would use the shelter for warmth."
On 23 March last year, Leslie Owen, was sleeping in the café when he was woken by Gizzi.
"He recalls being woken up by what he describes as a blow to his head," said Mr Medland.
"He could see that Mr Gizzi had a weapon. Mr Gizzi was under no conceivable threat from Mr Owen. The assault went on for quite a while."
Police during their investigation found the blood of another homeless man, who they discovered had been attacked by Gizzi two years before.
Gizzi and Fontenot also admitted assaulting a third man in November 2004, who claimed he had been attacked with a baseball bat.
This case was discovered after police listened into telephone conversations Gizzi made in his Bentley.
The court heard a listening device had been fitted during a surveillance operation.
Judge Elgan Edwards, recorder of Chester, took into account their guilty pleas, but said: "This kind of conduct, in your case Gizzi using violence towards people who may be a nuisance, is quite unacceptable.
"You should be making your livelihood not from crime, you have the intelligence to do it".
Lawyers representing the two men said their guilty pleas had saved a great deal of public money and they raised concern about the attention the case was attracting.
But Judge Edwards said: "I want to make it abundantly clear that Mr Gizzi and Mr Fontenot will be sentenced on the basis of what they pleaded guilty to and not tittle tattle and rumour".
Gizzi's barrister Duncan Bould said his parents and fiancee were standing by him.
Fontenot's barrister Gerry Baxter said his client was "very much the junior player, hired hand and acted as a courier".
Detective Superintendent Chris Corcoran after the case said: "[He's] Gizzi's lieutenant, another bully, a thug".
Gizzi lived in a £1.75m mansion in St Asaph and drove a £100,000 Bentley car.
He was brought to justice after police mounted a surveillance operation around nine months ago.
Supt Barry Jones, said: "Both Gizzi and Fontenot were regarded as bullies, who felt they were above the law and almost untouchable.
"As they serve their prison sentences the clear message is no-one is untouchable, especially in north Wales.
He added: "This has been a very, very important conviction."