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, also known as John Donohoe, was born in Dublin, Ireland around 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 from the Quakers Hill farm to the bush with two men named Kilroy and Smith. They formed an outlaw gang known as "The Strippers," as they stripped wealthy land owners of their clothes, money and food. Servants on the farms helped the bushrangers by providing 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 he 'boiled the billy' with Donahue, as a fifteen-year-old, when 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 was arrested with his gang for robbing bullock-drays on the Sydney to Windsor Road. On 1 March 1828 they were sentenced to death in the Supreme Court of Sydney by Judge John Stephen. Kilroy and Smith were hanged but Donohoe escaped custody. In 1829, notices distributed with a reward of £20 for Donohoe's capture, described 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 and for the next couple of years roamed the bush, bailing up settlers and plundering property from Bathurst to Yass and the Hunter region to the Illawarra.
As part of a group of 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 the soldier John Muckleston following a shootout between bushrangers and troops at Bringelly, New South Wales.
The Sydney Gazette on behalf of all respectable citizens rejoiced at John Donohoe's death. Smoking pipes made in the shape of Donohoe's head included holes representing the bullet-holes in his forehead. These pipes 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' and later published in 1853 as 'The Bushrangers'. Charles Harpur was inspired to write this play after the April 1829 shooting of a settler on the Hunter River by two bushrangers. Harpur was sixteen at the time and believed that one of the bushrangers was John Donohoe. 
Donohoe was also immortalised in the ballad 'The Wild Colonial Boy'. Authorities tried to ban the song, however were unsuccessful. Instead it became a ballad of defiance, being sung by generations of Australians and becoming part of Australian folklore. With time, the lyrics changed with the name of John Donohoe becoming Jack Doolan, Jack Dowling, Jack Doogan and even Jim Doolan. However, the ethos line that struck a chord with many Australians was "'I'll fight but not surrender till I die', cried the Wild Colonial Boy."
The Bob Dylan 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)
- Obituaries Australia entry
- Australian Dictionary of Biography entry
- Maitland Mercury and Hunter River General Advertiser, 31 August 1850
- Sydney Gazette and New South Wales Advertiser, 4 September 1830
- Index to Convict Arrivals 1788–1842