Jack Donahue (1804 – 1 September 1830) was a bushranger in Australia between 1825 and 1830. Known as "Bold Jack Donahue", he became part of the notorious "Wild Colonial Boys".
Early life and transportation
Jack Donahue, sometimes spelled Donohoe, was born in Dublin, Ireland about 1804. An orphan, he began pick-pocketing, and after later involvement in a burglary, was convicted of intent to commit a felony in 1823. He was transported to Australia in 1825. Upon being shown his cell at Carter's barracks, in Sydney, Donahue remarked 'A home for life'. During his early imprisonment, he was twice sentenced to fifty lashes as punishment.
Donahue escaped to the bush from the Quakers Hill farm with two men named Kilroy and Smith. They formed an outlaw gang known as "The Strippers," since they stripped wealthy landowners of their clothing, money and food. Servants on the farms sometimes provided them with information about their masters, and at times even provided them with food and shelter.
"Another time, near the same place ('the junction of the Bringelly and Cowpasture roads'), the notorious Donahue nearly got me. I had dismounted from my horse to remove some shifting rails, being a short cut through the bush to Prospect Hill, the residence of a friend, Mr. Lawson. I remounted my horse double quick, and most unceremoniously left the rails on the ground, and lost no time to be out of sight. He was accompanied by another bushranger."
Toby Ryan later recalled how he had 'boiled the billy' with Donahue, when as a fifteen-year-old, he was out looking for cattle near Llandilo:
"Donahue was the most insignificant looking creature imaginable, and it seemed strange that such as he was able to keep a country in terror for eight years. He was attired in a velveteen coat and vest, cabbage tree hat, moleskin trousers, and a blue nankeen shirt, with a heart worked on the breast in white cotton"."
On 14 December 1827 Donohue and his gang were arrested for robbing bullock-drays on the Sydney to Windsor Road. On 1 March 1828 Judge John Stephen of the Supreme Court of Sydney sentenced them all to death. Kilroy and Smith were hanged, but Donohoe escaped from custody. In 1829, notices were distributed with a reward of £20 for Donohoe's capture, describing him as '22 years of age, 5 feet 4 inches (163 cm) in height, brown freckled complexion, flaxen hair, blue eyes, and has a scar under the left nostril'. One year later the reward increased to £200.
Wild Colonial Boys
Donohoe evaded capture for the several more years, roaming the bush, bailing up settlers and plundering property from Bathurst to Yass and the Hunter region to the Illawarra.
As part of a gang of from ten to twelve men, he became one of the notorious "Wild Colonial Boys". 
On the afternoon of 1 September 1830, John Donohoe was shot dead by John Muckleston, following a shootout between bushrangers and soldiers at Bringelly, New South Wales.
The Sydney Gazette on behalf of "all respectable citizens" rejoiced at John Donohoe's death. Smoking pipes were made in the shape of Donohoe's head, including the bullet-holes in his forehead, and were bought and smoked by the citizens of Sydney. 
In 1833 John Donohoe's life was recounted in Charles Harpur's play 'The Tragedy of Donohoe', later published in 1853 as 'The Bushrangers'. Harpur had been inspired to write his play after the April 1829 shooting of a settler on the Hunter River by two bushrangers. Harpur had been sixteen at the time and believed that Donohoe was one of the bushrangers. 
Donohoe was also immortalised in the ballad 'The Wild Colonial Boy'. Authorities tried to ban the song, but failed. Instead it became a ballad of defiance, continuing to be sung by generations of Australians and becoming part of Australia's folklore. With time, the lyrics changed John Donohoe's name to Jack Doolan, Jack Dowling, Jack Doogan and even Jim Doolan. The ethos line that struck a chord was "'I'll fight but not surrender till I die', cried the Wild Colonial Boy."
Bob Dylan's album "Good as I been to You" mentions Donohoe in the song "Jim Jones":
"And it's by and by I'll slip my chains, into the bush I'll go.
And I'll join the brave Bushrangers there
Jack Donohue and Co."
- "BUSHRANGERS AND BUSHRANGING; ORAN OLD TALE RETOLD.". The Colac Herald (Vic. : 1875 - 1918). Vic.: National Library of Australia. 8 April 1879. p. 1 Supplement: Supplement to the Colar Herald. Retrieved 17 December 2013.
- Russel Ward, 'Donohoe, John (Jack) (1806–1830)', Australian Dictionary of Biography, National Centre of Biography, Australian National University, http://adb.anu.edu.au/biography/donohoe-john-jack-1985/text2413, accessed 30 August 2013.
- "Adventures of Robert Hoddle.". The Queenslander. Brisbane, Qld.: National Library of Australia. 26 August 1937. p. 3. Retrieved 18 December 2013.
- "History of Penrith.". Nepean Times. Penrith, NSW: National Library of Australia. 27 October 1949. p. 3. Retrieved 18 December 2013.
- "John Donohoe". Australian Dictionary of Biography. Retrieved 13 March 2013.
- Inglis, K. S., The Australian Colonists : An exploration of social history 1788–1870, p.169 (Melbourne, 1974)
- "ADVANCE AUSTRALIA Sydney Gazette.". The Sydney Gazette and New South Wales Advertiser (NSW : 1803 – 1842). NSW: National Library of Australia. 7 September 1830. p. 2. Retrieved 13 March 2013.
- Inglis, K. S., The Australian Colonists : An exploration of social history 1788–1870, p.263 (Melbourne, 1974)
- Inglis, K. S., The Australian Colonists : An exploration of social history 1788–1870, p.266 (Melbourne, 1974)
- "Jim Jones by Bob Dylan (arr)". Bob Dylan (Official Site). Sony Music Entertainment. 2015. Retrieved 2015-02-25.
- J. Meredith, The Wild Colonial Boy (Sydney, 1960)
- M. H. Ellis, "The Wild Colonial Boy", Bulletin, (Sydney, 25 Feb 1953)
- Frank Patrick Clune, Wild Colonial Boys (Sydney, 1948)
- Geoff Hocking, Wild Colonial Boys : tall tales & true Australian bushrangers (Victoria, 2012)
- Philip Butterss, Wild Colonial Boys' games: Bold Jack Donahoe to R. J. Hawke. -History of the Australian ballad (Melbourne, 1989)
- Inglis, K. S., The Australian Colonists : An exploration of social history 1788–1870 (Melbourne, 1974)