Transportation
For his part in the Fenian conspiracy, O'Reilly was sentenced to twenty years' penal servitude. It appears he was originally sentenced to death but his sentence was commuted to 20 years. He served nearly two years in English prisons before being put aboard the convict ship Hougoumont for transportation to the British colony of Western Australia. The Hougoumont's passage was the last convict ship transport to Western Australia. After arriving in Fremantle on 9 January 1868, O'Reilly was admitted to the Convict Establishment (now Fremantle Prison), but after a month he was transferred to Bunbury. He was assigned to a party of convicts tasked with building the Bunbury–Vasse road.
At Bunbury, O'Reilly quickly developed a good relationship with his warder Henry Woodman, and was appointed probationary convict constable. As assistant to the warder, he did record and account keeping, ordering of stores, and other minor administrative duties. He was frequently used as a messenger, which required him to travel regularly between the work camp and the district convict prison in Bunbury. The warder apparently used O'Reilly to maintain contact with his family, for the prisoner became a regular visitor to the Woodman family home, and at some point began a romantic liaison with Woodman's daughter Jessie. This ended badly, at least for O'Reilly; he wrote poetry expressing his agony of mind, and hints at romantic causes. On 27 December 1868, O'Reilly attempted suicide by cutting the veins of his left arm. After falling into a faint from loss of blood, he was discovered by another convict, and his life was saved.
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