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I first heard of Martin Cash while visiting the Officers Quarters Museum at Eaglehawk Neck. According to the audio-visual display, a group of runaway convicts including Cash actually managed to get past the Dogline!
Born in Ireland, Cash started off as a farm boy. In 1827 he was charged with housebreaking. According to Cash himself, he had shot at a man caught embracing his (Cash's ) mistress. He even included the detail that he had injured the victim in the buttocks!
For his crime, Cash was transported to Sydney for seven years. In 1837, he went to Tasmania. A few years later, he got himself in trouble again when he was charged with larceny. He got another seven year sentence for that.
During the next three years, he escaped three times. On one occasion he managed to stay free for two years. Eventually though he was re-captured and returned to Port Arthur with an additional four years added to his sentence.
Before long he had escaped again with a couple of experienced bushmen, Kavenagh and Jones. The three men became known as "gentlemen bushrangers". Apparently, even though they committed acts of robbery, they tried to avoid any violence if they could help it.
In time, Cash was captured again. This time he was sentenced to death for killing one of this pursuers. Luckily for Cash, at the last minute, the decision was overturned. Cash was sent to Norfolk Island for ten years. He seemed to have mellowed by this time. He was put in charge of the boys' dormitory and busied himself as a hat-maker.
In 1854 he obtained permission to mary Mary Bennett, a female convict, also from Ireland. Several months later, they were back in Tasmania. He took up respectable positions such as constable for the Cascades Agricultural Settlement and overseer at the gardens in the government Domain, Hobart.
On receiving a pardon in 1856, he went to New Zealand and lived there for four years. On his return to Tasmania, he bought a property which he farmed until his death in 1877.
It's clear to me that Cash managed to get past much more than just the Dogline. He could have been sentenced to death or transportation for life. Instead he was able to enjoy some comfortable positions, including owning his own property.
Apparently Martin Cash had great charm plus a reputation for chivalry even as a criminal. Under the circumstances, he certainly managed to do well for himself. I'm sure many other convicts would have liked to possess his talents!