Bankrupt ex-billionaire Sean Quinn, whose son and nephew have been jailed for contempt of court.

Bankrupt ex-billionaire Sean Quinn was facing the battle of his life last night to free his son who has been jailed over an asset stripping plot.

Sean junior and his cousin Peter Darragh Quinn, who has a warrant out for his arrest after failing to turn up at the High Court in Dublin for the hearing, were sentenced to three months in prison for trying to hide a €500m property empire from the former Anglo Irish Bank.

Quinn senior, once Ireland’s richest man, was also found guilty of the offence by the High Court in Dublin three weeks ago but the 65-year-old was spared punishment for now to give him time to comply with court orders and unravel the moves that carved up the family’s international property empire.

He clutched a handkerchief and bowed his head as the High Court in Dublin ordered his son be locked up.

The arrest of his nephew, the son of Peter Quinn, a former president of the Gaelic Athletic Association (GAA), was ordered after he failed to turn up for the hearing, leaving a message that he was sick.

Quinn senior refused to comment on the jail terms as he left the Four Courts in Dublin and only told reporters: “Have a good weekend.”

The one-time industry, insurance and property tycoon’s doomed gambles on Anglo have lumbered the family with a €2.8bn debt and a jailed son.

Judge Elizabeth Dunne told the men their contempt of court had been outrageous and that she was unhappy with their lack of cooperation.

During arguments against jailing the men, Brian O’Moore, senior counsel for Quinn senior, said it was wrong to lock up one member of the family in the hope another would act.

“This almost medieval approach of holding the son to see what the chieftain father will do in terms of freeing the son’s liberty is wholly inadequate,” he said.

Judge Dunne said it was far from medieval, but a practical way of trying to encourage compliance with orders.

She refused to accept they had no control over assets, when eight members of the family received €2.8m in pay and income from their firms since April 2011.

And she hit out at the movement of €1m to lawyers in Russia.

The bust business tycoon owes Anglo, rebranded as the Irish Bank Resolution Corporation (IBRC), €2.8bn after running up unprecedented losses through secret stock investments in the bank as its share price collapsed.

The Quinns admit that they owe €455m, but have refused the claims on the rest.

The contempt centres on a High Court order made in June 2011 which told the three Quinns not to act to put assets beyond the reach of the former Anglo.

Last month the court found the three Quinns consciously defied and misled the courts as they shifted family assets as far afield as Ukraine, Russia and Belize.

She accused the men of engaging in complex and costly steps to put the assets of Quinn’s international property group beyond Anglo in a blatant, dishonest and deceitful manner.