''Like many an expectant heir before him, he has not made the most of his opportunities, imprudently assuming that he and his brother would inherit their grandfather's estate,'' he said.

Robert had been given a ''better start than most young men could have expected'' and his tuition and boarding at The King's School had been paid by his grandfather.

The court heard Robert had been self-employed since about 2001 and was living in shared accommodation at Darling Point. At a hearing in 2012 he said he was living in a garage, sleeping in a swag and had virtually no assets.

Justice Pembroke said that ''no one is responsible for the position in which Robert Wilcox now finds himself, except himself'' and he doubted he was ''sufficiently motivated to find work''.

The grandfather left his estate to his only daughter in the expectation that her sons would inherit it when she died. “Unfortunately, instead of waiting for events to run their natural course, the sons sued their mother ... resulting in unquantifiable family discord, substantial cost and considerable hardship,” Justice Pembroke said.