John was born in Ireland in about 1806. He was transported under a life sentence of ‘Intent to commit a felony’, and arrived in Sydney on 2 January 1828, aboard the ship ‘Ann & Amelia’
He was first assigned to John Pagan at Parramatta, and then following a short stint on a chain-gang for misbehaving, was sent to Major West, who had an estate near Quakes Hill. It was not long before he took off with two men named Smith and Kilroy, and after robbing several bullock drays on the Sydney to Windsor road were captured and sentenced to death. While being escorted from the court to Sussex Street Gaol, Donohue escaped but not so his companions who were hanged.
John teamed up with several others including, William Underwood and together they plundered near and far. From the Hunter River Valley to Liverpool, and out through Bathurst, Yass, Burrungong, Campbelltown, and Liberty Plains. During this period he was nicknamed "The Stripper", either because he made people take their clothes off, or because he stripped them of everything they possessed. The folklore of ‘Bold Jack Donohue’ is more like that of Robin Hood. A bold, handsome man who was the hero of the oppressed convict gangs. The truth was that he was about five feet four inches in height, had a brown freckled complexion, flaxen hair and blue eyes, and was described as an undersized specimen with weak eyes. Some reports stated that he tormented his victims and may have burnt one squatter alive. Initially a reward of £20 was offered for his capture, but this was extended to an offer of ‘An Absolute Pardon and Free Passage to England, or a grant of land’, and still no arrest followed.
Eventually however, the police finally caught up with Donohue near Campbelltown on the 1st of September 1830, when he and the gang were surrounded by a detachment of soldiers. During the shoot-out Donohue taunted the soldiers with ‘the most insulting and indecent epithets’. But Private Muggleston fixed that by shooting him through the head. But the legend of ‘Bold Jack Donohue’ lived on in a song until it was banned by the authorities. Not to be beaten, however, it continue on with the named changed to ‘Jack Doolan’ and finally ‘The Wild Colonial Boy’.