William Westwood (also known as Jackey Jackey) was often referred to as a "gentleman bushranger" because of his dress and respect for his victims. He got the nickname 'Jackey Jackey' from the aboriginal people.
William Westwood was the eldest child of James and Ann Westwood and was born on 7 August 1820, in Manuden, Essex, England. He was baptised on 27 August 1820 in the Church of St Mary the Virgin. On 10 March 1835 William and Benjamin Jackson, both aged fourteen, appeared at the Essex Lent Assizes in Chelmsford charged with highway robbery. They were accused of stealing a bundle of clothes from Ann Saunders on the road near Manuden. William was found guilty and sentenced to twelve months imprisonment with hard labour in Chelmsford Gaol. His accomplice, Benjamin Jackson was sentenced to be whipped, and discharged.
Released from gaol in 1836 William soon fell into bad company. On 3 January 1837 William, aged 17, together with James Bird, aged 21, appeared at the Essex Quarter Sessions in Chelmsford. The two were charged with stealing a greatcoat belonging to John Rickett that he had left in a stables in Manuden overnight. Westwood and Bird took the stolen coat to a clothes shop owned by John Warner in Hare Street, Hertfordshire where they sold it for 6 shillings. In need of a replacement coat Rickett called at John Warner's shop the following day where his stolen coat was offered to him. Westwood and Bird were quickly identified as the culprits and arrested by Constable Charles Moss. At their trial Bird was acquitted but William was found guilty and, because this was his second offence, sentenced to transportation for 14 years.
On 2 February 1837 William was delivered to the prison hulk 'Leviathan' in Portsmouth Harbour where he was held before being transferred to the ship Mangles which sailed for NSW on 18 March 1837. He arrived in Sydney on 9 July 1837. He had several tattoos on his arms and a scar on his face.
Upon arrival in Sydney, Westwood was assigned to Phillip Parker King at his property, 'Dunheved' in Rooty Hill (near Penrith in western Sydney). In late December 1837 he was sent to the family property, 'Gidleigh' near Bungendore, NSW. The overseer of this location mistreated Westwood, not providing sufficient food and clothing. He tried to run away from his employer on more than one occasion, but each time was recaptured, beaten, and then put back to work. After stealing wheat, Westwood was sentenced to six months working on the roads in a chain gang on 19 April 1838. Once again escaping and being caught, Westwood publicly received 50 lashes on 4 February 1839.