James Freeman – ‘Hang or be Hanged’. 


Part of the original document pardoning a convict if he acts as executioner

Extract showing a pardon on condition of becoming the public executioner. Dated 1 March 1788, signed by Governor Arthur Phillip.

‘For here was an opportunity of establishing a Jack Ketch who Should, in all future Executions, either Hang or be Hanged’. Dr John White, Chief Medical Officer, First Fleet Journal.

1788 –  Friday 29th February: Shaped as another busy day for the infant colony’s’ criminal court. At 8 am to avoid Sydney’s intense midday sun and drenching humidity, after the long drawn-out dramas of the previous two (2) days it had been decided court would convene earlier than usual. See: From Here To Eternity  See: Blind Man’s Bluff – Hall and Lavell

29th February: Accused the previous day of stealing from government stores, James Freeman and William Shearman, were first to appear in the dock.

Both were found guilty.  Shearman was sentenced to 300 lashes. Freeman was condemned to die.

Next to appear George Whitaker, Daniel Gordon and John Williams were charged with stealing eighteen (18) bottles of wine.

Whitaker was discharged. Gordon and Williams, both Afro -Americans who as Loyalists had fought for Britain in America’s War of Independence (1775-1783), were found guilty and sentenced to hang with Freeman. The executions to take place that afternoon.


‘For maximum effect there had to be maximum ceremony…the wretchedness of the captive[s] were acted out in a procession which every citizen might see’. Richard Byrne, Prisons and Punishments of London, Grafton Harper Collins, London. 

As the previous day with Joseph Hall and Henry Lavell and, at Thomas Barrett’s execution on the 27th,’in case an insurrection should take place the battalion was under arms’ with musket, bayonet, fife and drum. Act 1 – From Here To Eternity

In drenching humidity the bedraggled convicts sat in a circle. Soldiers at the ready sweltered in their heavy scarlet woollen uniforms.

A silent unseen Aboriginal audience watched wondering what new and strange torment they would witness.

In chains Freeman, Gordon and Williams ‘marched to the execution place‘ in what Lieutenant Ralph Clark described as ‘extreme misery’.   At 4 pm the rituals of hanging – prayers, nooses and head-coverings – began.

In a repeat performance of his macabre antics the previous day, at the very last moment, Marine Captain David Collins approached Provost-Marshall Brewer.

Gordon and Williams were granted conditional pardons.  Head- coverings and nooses were removed and they learned their fate. They would join Joseph Hall and Henry Lavell, who the previous day, had cheated death. See: Act 2  Blind Man’s Bluff – Hall and Lavell.

The four (4) men were to be chained indefinitely onto Pinchgut a rocky outcrop in Sydney Harbour.

Court papers note; Phillip, who also served in the American war, later wrote to Lord Sydney; ‘when the season permits I intend  Gordon and Williams [Loyalist Afro-Americans] be exiled from the settlement…to the South Cape’ on the coast of Van Diemens Land, now Tasmania.


Freeman  ‘with the rope about his neck’ heard judge-advocate Captain David Collins confirm his death sentence. Then Collins made James Freeman an offer.

‘But while under the ladder, with the rope about his neck, he [Freeman] was offered a free pardon as condition of performing the duty of the common executioner as long as he remained in this country, which after some little pause, he reluctantly accepted’. John White. ibid.

1788 – 1 March: Governor Arthur Phillip signed Freeman’s ‘Reprieve from Death’.

‘Whereas [James Freeman] tried and convicted of Felony and received sentence of death for the same….In pursuance of the Power and Authority vested in me I [Arthur Phillip] do hereby grant him the said [name erased from document] a pardon for the said Offence, on Condition of his becoming the public Executioner for and during the term for which he was transported to this Country’. White. ibid.

Young James Freeman’s life hung in the balance with every death sentence. The infamous contract ‘either Hang or Be Hanged’ endured; ‘for and during the term for which he was transported’.

1788 –  2 May, Sydney: Freeman took his first life – John Bennett – on the 2nd May 1788. Aged 20 years Bennett was a year younger than his executioner.


1789 – 25 March, Sydney: Perhaps Freeman’s most bizarre moment came when, one by one he hanged six (6) marines ‘the flower of the battalion’. 

Over a number of months, using counterfeit keys, these soldiers had systematically robbed the government storehouse. See:Smallpox Dead Aborigines Don’t Eat

1789 – 2 December, Sydney: Freeman’s worst moment however may have come on the 2nd of December 1789 when he hanged Ann Davis the first white women executed in Australia.

A week later Freeman was found drunk and punished with one hundred (100) lashes. See: Ketch Connection

Verbatim accounts of these proceedings have been preserved and held in the archives of the Supreme Court of New South Wales. Facsimiles published in 1913 are available at the Mitchell Library, Sydney.


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