John Sleigh, a Trial Bay Gaol prisoner, used nautical skills acquired aboard a training ship for juvenile offenders to gain his freedom in a daring rescue in August 1899.
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However his troubled life was to end on the gallows at Goulburn Gaol the following year.
John Sleigh was born around 1859 but as he used other aliases, such as Frank Ward and Frank Quinlan, during his life this cannot be verified.
The former merchant ship Vernon, purchased in 1867, was set up as a training ship to rehabilitate and train juvenile offenders, and it was here Sleigh was sent at the age of nine for theft.
The boys were given moral training, nautical and industrial training and instruction, and elementary schooling.
From there, John was said to have been hired out to a farmer in the Richmond River District. His first brush with the law came on March 3 1874 when he was sentenced to two months hard labour for larceny.
He served further gaol terms over the next few years for shooting with intent, horse stealing, larceny in a dwelling and assault with intent to rob.
For the latter crime, he was sentenced to fifteen years in prison and whilst serving his term in Penrith Gaol, John Sleigh made a savage attack on a prison guard.
The guard was later to die from his injuries and Sleigh was sentenced to death, although this was later commuted to life imprisonment.
For one reason or another, John Sleigh was transferred to Trial Bay Gaol.
On a stormy night in August 1899, Sleigh was among a crew of prisoners who launched the prison whaleboat to rescue people aboard the steam launch Daisy which was in danger of sinking in Trial Bay.
For his part in this, Sleigh received his ticket-of-leave.
He did not stay in Kempsey long however, and made his way to Back Creek, near Bombala, where he moved in with his aunt, Mrs Michael Woolfe.
Michael Woolfe left the family to go to Bombala one day and gave his son Henry and Sleigh a shotgun and a rifle and suggested they go out and shoot some game.
Instead of shooting game however, Sleigh went to a distant paddock where Michael Woolfe's stepbrother, Francis Curran, was working and shot him with the rifle, mortally wounding him.
Curran was supposed to have remarked: "I knew that rifle would go off sometime and shoot somebody!"
Sleigh was arrested the following day after a violent struggle with the police and put on trial for Curran's murder.
He had no motive for Curran's murder and was known to suffer epileptic seizures.
Two doctors were called in to assess Sleigh's mental condition however they found he was sane when he committed the offence.
In October 1890 Sleigh was found guilty of the wilful murder of Francis Curran and sentenced to death by hanging.
In his cell, Sleigh would sing endlessly in his fine baritone voice popular songs of the day such as Annie Rooney, Dreaming of Home and Mother and other favourites.
This time there would be no reprieve however and on Wednesday morning, December 5 1900, John Sleigh was hanged in Goulburn Gaol.
