Though O'Reilly has strong ties to Boston, he was born June 28 1844 in Drogheda, Ireland where his father, William O'Reilly worked at the local school, and his mother, Elizabeth O'Reilly helped manage an orphanage. Both William and Elizabeth O'Reilly had a strong passion for writing and literature. Their appreciation for literature was instilled during O'Reilly's adolescence. His first job was an apprenticeship under the employment of the Irish printing company Drogheda Argus. His job required him to hand out literature and pamphlets protesting the British occupation and rule, in Ireland. At the age of 15, O'Reilly was forced to look for a new career after Drogheda Argus closed down. O'Reilly left for England where he continued his journalistic career at another printing company, Preston Guardian, where he soon became a reporter.
O'Reilly returned to Ireland at his father's request at the age of 19. He soon became involved with the Fenian Brotherhood, an organization that assembled to protest against the British rule in Ireland and advocated for Irish freedom. O'Reilly enlisted in the army, but only to recruit men to betray the British and fight on behalf of the Irish. He successfully recruited men, but his work was halted after the British raided the office of The Irish People, a newspaper founded by a member of the Fenian Brotherhood. During their raid the British found files with names of members involved with the Fenian Brotherhood, including John O'Reilly. Due to this, O'Reilly was captured by the British for acts of treason.
O'Reilly's trial began a day before his 22nd birthday. He was tried for mutiny. He was charged with treason and sentenced to death. Due to his young age, his sentence was lessened to 20 years of penal servitude. O'Reilly bounced around to different prisons in both London and England. He once escaped prison but was soon recaptured and sent to Australia's penal colonies to finish his sentence. While in Australia, O'Reilly used his love for literature and writing to his advantage and befriended Father Lynch, an Irish priest. This friendship was short lived for O'Reilly was then transferred to another convict camp in the Koagulup swamp. Before his transfer, Father Lynch told O’Reilly that Father McCabe would look out for him during his time at his new place of work. Father Mac followed through with this and helped O’Reilly escape to America. At this point in time, Americans had a strong anti-British attitude. Father McCabe was able to convince two captains to help O’Reilly with his escape. O’Reilly soon boarded the Gazelle and was on his way to America, and arrived in Philadelphia in November of 1869 where he was welcomed warmly by many members of Fenian groups.
O’Reilly received a job at the Inman Steamship Company, but was fired after the English owners soon discovered his identity. He then moved to Boston. Soon after his arrival, he found work in a field more attuned to his interests and became a reporter for the Boston Pilot, a newspaper recognized for giving a voice to the Irish. During O’Reilly’s reporting career, his political values changed as he became more interested in Fenian involvement. He soon became co-owner of the Pilot along Archbishop Williams of Boston. O’Reilly used this platform to once again advocate for the rights of marginalized communities including Jews, American Indians and Blacks.
O’Reilly also was a poet and published many works recounting his experiences through the medium of poetry and literature. One of his most well known pieces was the novel, “Moondyne” which retells his experiences in Australia. Moondyne was published in the year of 1879.
On August 10,1890 John Boyle O'Reilly passed away. He was found by his wife at their residence in Hull. His death was due to an overdose of the drug chloral which he often took as a remedy for insomnia. His grave can be visited at the Holyhood cemetery in Brookline.