When Jimmy was just 15, he was sent to Sydney to the only boys' reform school in the state, an industrial training ship called the Vernon moored near Cockatoo Island.
He was sent there after being convicted of 'horse sweating', 'borrowing' someone else's horse and riding it without permission until it was exhausted.
Similar to 'joy riding' in a car today.
It was not strictly 'horse stealing' and only became so if the offender attempted to sell the animal, as if it were his own.
Jimmy was apprehended not long after his father was put in Maitland gaol in September 1890 for stabbing another blackfellow at the camp where he and his son were staying after an argument.
The boy aged around 15 then became homeless and without any means of support.
Jimmy's youngest brother, Roy, was a 'career criminal', spending much of his adult life in gaol.
He was in Goulburn gaol in 1918 and Bathurst gaol in 1923.
Roy's main offences were stealing, breaking and entering and attempted burglary, but he also was out to get Mick O'Brien, whose pregnant wife and toddler son his older brothers, Joe and Jimmy had murdered.
Jimmy was in Darlinghurst gaol for around three months from the end of 1900 to early 1901 before he was hanged.
His brother Joe would have been there too if he had not been shot and killed.