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Early one morning in May 1860, Joseph and another man called Henry Howden, were in a cart, near Boston cemetery when they were stopped by Police Constable Bates of the county constabulary. The cart contained something bulky. Bates found some sacks of wheat in the cart and, as neither men could give an expanation for them, he attempted to take both men into custody. There then followed a violent struggle and Joseph got away. The following morning he was seen by two policemen near Mount Pleasant bridge at Frithville. A lengthy chase followed and once again Joseph escaped, this time by swimming across a drain. However his luck was running out, and he was later apprehended just as he was entering Boston.
At the Quarter Sessions held at Spilsby on the 10th July 1860, Joseph Carey and Henry Howden were found guilty of stealing forty seven stones of wheat, the property of John Thompson of Frithville. Joseph was sentenced to three years penal servitude and Henry Howden was given nine months hard labour at Louth. Joseph served his sentence at Portland Prison, in Dorset.
This was not the end of Joseph`s criminal deeds. On the 25th October 1864 he was convicted again, for stealing eight stone of wool locks, the property of Joseph Caudwell of Frithville. This time he was sentenced to seven years penal servitude. He was first sent to the prison at Lincoln, then on the 19th December 1864 he was sent to Wakefield Prison. He was transferred to Chatham Prison on the 10th October 1865, were he staid until the 27th March, 1867. He was then sent by rail to Sheerness where he boarded the Norwood, which set sail for Portsmouth and Portland on the 28th March 1867. Picking up more convicts on the way.
On the 18th April 1867, the Norwood left Portland, for Western Australia. They arrived of the Fremantle on the the 13th July 1867. Around 5 p.m. the pilot, a man called Jacklin came aboard and the ship dropped anchor at 6.30 p.m. At 9.45 a.m. on the 14th July, guards from Fremantle Prison came aboard. At 1.00 p.m. all the prisoners were disembarked.
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