John Smith was born in Manchester in 1787.
The details of his early life are unknown, however at age 20 he was no more than a petty criminal similar to thousands of others transported to Australia to serve out their sentences.
That his success began with subterfuge and good luck is undeniable however he must also have possessed qualities that allowed him to stand out from his fellow prisoners, especially at the bleak little penal settlement at Newcastle where he progressed from the status of a thrice convicted criminal to become chief constable, entrepeneur, innkeeper, land owner and ship owner.
He was an extraordinary man who made an unparalleled contribution to the early settlement and growth of Newcastle and Maitland over the next fifty years.
His story would be unbelievable but for the paper trail he left in the Colonial Secretary's Correspondence and elsewhere as can be seen in some of the document below.
John Smith's history relative to Australia began in 1809 when at the Salford, Lancaster Quarter Sessions on 11 October he was sentenced under the name of James Sidebottom to seven years transportation.
James Sidebottom was sent to the prison hulks at Portsmouth where he was admitted on 18 December 1809, from which he was sent on board the Indian for transportation to New South Wales. 
The Indian arrived in Port Jackson 16 December 1810. On 16 December 1811 James Sidebottom was reported as having absconded from Eber Bunker at George's River.  He was still absent in January 1812 .
John Smith at Leicestershire in 1813
It hasn't been traced how he escaped from the colony, however by his own admission, in January 1813 under the name of John Smith at Leicester Borough Quarter Sessions he was convicted of stealing a quantity of stockings and sentenced to 7 years transportation.  No mention was made in the newspapers that he had returned from transportation.
He was sent to the Retribution Hulk on 28 May 1813 and sent to the General Hewitt for transportation on 6 August 1813.  The General Hewitt arrived in Sydney on 7 February 1814.
Marriage at Parramatta 1814
At St John's Parramatta on 11th July 1814, John Smith married Mary Furber. Mary was the widow of William Furber and had a young son George Furber.
Sent to Newcastle 1815
The Sydney Gazette on 24 June 1815 records the trial of John Smith in Sydney that would see him sent to Newcastle penal settlement. The trial was the first at the Court assembled for the first time at the apartment fitted up in the new General Hospital. For burglary in the warehouse, making part of the premises of Captain Brooks, and stealing tobacco to the value of 20 pounds and upwards, he was acquitted, however was found guilty of the lesser charge of stealing from the warehouse. 
He was sent to Newcastle on the Lady Nelson on 8 July 1815. Lieutenant Thomas Thompson was commandant of the settlement at this time.
The document below is so interesting in the history of Newcastle for as well as John Smith on the Lady Nelson that day were also well known artist Joseph Lycett and Henry Dale who became one of the first gaolers at the Newcastle gaol.
Captain James Wallis took over the Newcastle settlment as Commandant in June 1816 and it was in these years that John Smith began to shine. Many of the convicts in these years were sent to labour in the government coal mine, the lime burners or town gangs where conditions were harsh and punishment severe. John Smith may have been assigned to government in this way, however if so it wasn't for long.
Chief Constable at Newcastle 1817
Correspondence below dated 1823 reveals that John Smith was appointed Chief Constable at Newcastle in 1817.
When Major Morisset became Commandant at Newcastle in 1818 he requested the full details of John Smith's former offences as well as the ships he arrived on. The following correspondence was sent in reply:
This explanation of his previous sentences must have met with Major Morisset's approval as John Smith continued in his position as Chief Constable.
...Newcastle in 1818
Land Grant near Maitland
After Governor Macquarie visited Newcastle in 1818, John Smith was also granted land near Maitland. The location of his land near Maitland can be seen in the lower right corner adjoining Eales' land on the map below. It may have been land that in 1836 was advertised for sale as a 460 acre dairy farm. 
How he came by his Maitland land is revealed in his correspondence to the Maitland Mercury regarding the proposal for a court house at Maitland.......
GENTLEMEN- It appears, from the Mercury of to-day, that there is a great contention betwixt the East and West Maitland folks, as to where the court house shall ultimately be established : permit me, as the oldest settler on the Hunter River, to make some few remarks on this important subject.
The Maitland district was established in October, 1818, by Governor Macquarie. Two others, with myself, were permitted to select each a farm in any part of Maitland where we thought proper, and he gave me a written order that I should have the first choice. This indulgence was given for the services rendered on the occasion. All three of us fixed on land in East Maitland, considering it was the best place for a township. Many of the West Maitland folks will think the same should they happen to be visited by such a flood as there was in 1819 ; and this may happen again. I was one of those who, on that occasion, went to West Maitland to take some of the settlers from the tops of their houses, in a large boat, and landed them on the hill behind the old court house 
In March 1819 John Smith requested that he be granted leave of absence from Newcastle to attend to urgent matters which request, although it caused great inconvenience, was granted by commandant Major Morisset.
Conditional Pardon and Town Lease at Newcastle
In September 1819 in correspondence from the colonial secretary's office it was confirmed that John Smith was approved to receive a town lease at Newcastle and a conditional pardon. 
His correspondence dated January 1823 reveals his early contribution to Newcastle.....
The Memorial of John Smith, humbly shewing that...Memorialist filled the station of Chief Constable of Newcastle with vigilance and credibility to the Settlement of Newcastle for the last six years; and has recently resigned the Office from its materially interfering with his domestic duties.
That Memoriaist obtained permission from the present Commandant of the settlment to build on a spot appointed for the purpose; that memorialist at a considerable expense and a good dwelling house in the line of *George Street as marked out by the Surveyor General consisting of eight rooms with other appurtenances; and has procured a regular registry of the same in the Government Office.
That Memorialist having a numerous and ever increasing family to provide for most humbly entreats His Excellency will be pleased to grant him a town lease; as this circumstance is in a great measure very intimately blended with Memorialists future interest in Life.  *George Street was later re-named Watt Street.
Public House at Newcastle
The above mentioned dwelling house in George (Watt) Street Newcastle became a public house known as the Newcastle Hotel and also known as the Crown Inn. The Store and Public House can be seen on John Armstrong's 1830 map of Newcastle.
Select here to find other convicts assigned to John Smith
Life at Newcastle
In 1828 John and Mary Smith with their seven children resided at Newcastle. Also living with them was 18 year old George Furber, the son of Mary and her first husband.
Newcastle was full of thieves and vagabonds in these early days and anyone who ran a business or owned a vessel had to be ever vigilant or suffer the consequences. Although he had been a convict himself, John Smith was not against having his own assigned servants taken to court and charged with crimes or misdemeanours. Sometimes these men (and women) were severely punished.......
In 1824......William Aibery in the service of Mr. J. Smith. Charged with neglect of work and refusing to obey his masters orders and for theft. Mr. Smith states....that he sent the prisoner up the river in company with Thomas Evans to procure timber. That instead of returning in two days they were absent five and only brought back two days work with them. He further stated that he has ordered them to attend Divine service but they have refused. He also states that a few days since he detected Aibery after he had been milking with a batch of milk in his bosom. William Aibery sentenced to 50 lashes. Thomas Evans sentenced to 25 lashes.
In 1824......Henry Butler per Guildford and Thomas Jones per Grenada both in service of government charged with theft....Chief Constable James Calvert states....On Sunday afternoon the 10th inst., I was sent for by John Smith to take charge of the prisoners who he informed me had been attempting to rob his till. Mr. Smith showed me a bank note and some silver which he said had been taken out of the till and thrown by Butler into a cask in the yard as he attempted to make his escape. I searched the prisoners and found a Spanish Dollar concealed in Jones mouth. They were both intoxicated. Mr. Smith states....The prisoners were at my house and I heard someone in the shop. My wife went out and caught Butler at the till. He endeavoured to make his escape and threw some money away which was afterwards picked up. One of the dollars was picked up by Jones who put it in his mouth from where it was afterwards taken by the Chief Constable. Henry Butler and Thomas Jones both sentenced to 75 lashes and hard labour in the gaol gang until further orders
In 1829 Richard Bannister, charged with disobedience of orders; Mr. John Smith deposed as follows: The prisoner is my assigned servant, stationed at my farm at Wallis Plains. He demanded a pass from my son on the plea of attending the hospital, he having a scalded foot. He was refused the pass but he went away to Newcastle 18 miles distant. Dr. Brooks the colonial surgeon said the man had no just cause to leave the farm for the hospital, as the injuries to his foot were not at all serious. Sentence 75 lashes.
in 1835.... Sarah Barnett per Buffalo assigned servant to Mr. John Smith, charged with disorderly conduct.. Mr. Smith testified....Having heard that the prisoner had destroyed a number of things and was insolent to her mistress, I sent my daughter for her, that I might speak to her. She refused to come. I then sent the man servant to bring her to me. Upon my reproving her for her insolence, she said she did not care, that the Magistrate could not hang her and in other respects her behaviour was dis respectful....Sentenced to 7 days in the cells.
John Smith continued to reside at Newcastle for many years and also owned substantial properties at Maitland including a steam flour mill and The Black Horse Inn at at East Maitland. Despite his success or perhaps because of it, he was not accepted by some of the emigrant settlers as the following extract from an article, favouritism amongst the Hunter River Magistrates published in the Sydney Monitor in February 1833, shows:
Mr. Maurice Townsend went up to the door ofMr. Muir's Inn, flushed with the victory he had achieved over the yielding carcass of the carrier's assistant, and seeing Mr Smith (a respectable Emancipist, who goes by the friendly name of Gentleman Smith,) he took the trouble to inform him, in terms and gestures of wrath, that if he, Mr. T. could find Mr. Fleming, he would shoot him. Mr. Smith replied, he had better not do anything of the kind, but go home. Such free, friendly counsel as this, was not to be endured by Emigrant blood, and therefore, making no more ado, Mr. 'T. clenched his fist, advanced towards Mr. Smith, and after informing him ' he was a d.....d treble-convicted convict scoundrel, he floored him then and there. Next day, when Mr. Maurice Townsend found himself sober, he began to ponder his ways. The first thing he did, was, to seek out the carrier's man, and pay him for the chastisement which he had inflicted on him the day before. The next question was, what shall I do with Smith ? Mr. Smith appealed against Mr. Townsend, and the latter finally appeared at the bar of the Quarter Sessions at Maitland, and was found guilty of the assault.
John Smith died in 1870 and was buried in Christ Church Burial Ground at Newcastle......
Right in the corner of the church yard near the entrance gate, there is a substantial but time worn tomb, in which were buried several members of the Smith family. The head of the house who was familiarly called Gentleman Smith, was quite a character in his way, and for years resided in a house at the corner of King and Pacific Streets, which is now occupied by Mr. McFarlane. He was in many respects a quaint personage and for years kept his coffin in a room and the back of the dwelling. The coffin was made of polished cedar but the lid which was a beautiful piece of timber was stolen by a man working about the place, and converted into other uses. Another eccentricity was the old mans habit of hiding money in odd corners. One day an old servant was rummaging about in the cellar, when he discovered quite a large sum in guineas which had been planted there for years. Smith built the Naval Brigade Hotel and the white buildings which stand on the south side of King Street facing his residence. Many years ago he is reputed to have worked the old coal shaft upon which the bowling green in the big Reserve is situated. He died a wealthy man leaving large property interests in the city. 
Notes and Links
1). Above the Black Horse Inn - Cultural Collections, University of Newcastle
2). Find out more about John Smith at NSW Heritage
3). George Furber married Mary Ann Muir, the daughter of Constable George Muir. Mary Ann Muir probably moved to Maitland with her mother Elizabeth in 1829. Elizabeth managed Alexander McLeod's new Inn until George Muir resigned from his position as constable in Newcastle in 1830. George Furber and Mary Ann's time together was brief. Their son George died in 1836 and Mary Ann after a long and painful illness died at the house of her mother in Maitland in April 1837. Two children survived from their marriage and George remarried soon after Mary Ann's death. He and his new family eventually moved to Queensland where in 1855, he was brutally murdered by aborigines.
4). John Smith also owned the sloop Elizabeth which was almost lost at Newcastle in 1827......
Newcastle - On the morning of the 27th the sloop Elizabeth, belonging to Mr. John Smith,. of this place, attempted to round Nobbys after the top of high water ;- it was blowing very strong; at S. S. E. .with a considerable sea on. The Master of her, it is presumed, had run in under the impression that the flood was still making, and that he might save his distance. He was in some measure justified in acting so, as the signal heretofore used, forbidding vessels to approach the harbour on the, ebb tide or bad weather, was not (indeed could not be) .made - ALL the flags heretofore used signals being warn out
The consequence was, the little vessel was swept down into the bight, and obliged to let go her anchors, which held her about two hours, during which time the sea made, a complete breach over her. At last her anchors came home, and she drifted into the surf, and when at about the distance of 200 yards from the Beach, at a most critical moment, and when all hope of saving her was abandoned, the wind shifted to south west; the people on board made sail, slipped the cables, and got her head to sea, and before sunset she was out of sight . We are still anxious about her fate, as she has neither anchors nor cables on board. She would have been a loss to, her owner of upwards of four hundred pounds, not to mention the almost certain loss of four lives, for there was little chance of their being saved in the tremendous surf that was running.
All this risk and anxiety might 'be avoided, if government .would be at the paltry expense of sending a few yards of bunting to make signal flags, which, till within these ten or twelve months were always supplied and signals accordingly made, which either enabled vessels to approach the harbour with safety, or acted as a caution for them to stand to sea, and yet the harbour dues on Colonial craft are enormous., There is, not a flag here to, hoist, except the Union Jack, and one or two private signals...The Australian 6 January 1827
5). UNLAWFUL DETENTION OF PROPERTY,- On Thursday last John Smith, usually known by the appellation of 'Gentleman Smith' appeared before the bench at the police office, Newcastle, to answer a charge of having unlawfully detained one iron stretcher, the property of Mathew Teasdale of Newcastle. The stretcher had been purchased by Teasdale from Mrs Gorrick. whose family lately resided in the house when Mrs Gorrick left Newcastle. A young man took the stretcher away bv Smith's orders, so that when Teasdale went to take it away it was gone. This constituted the gist of the case. Smith stated that the complainant had no written order fromMrs Gorrick to take anything away from the house and whatever things were left in the house, under such circumstances, belonged of course to him, or at least were under his care. The defendant was ordered to give up the stretcher and pay one guinea professional costs, and Court costs. - Northern Times 13 March 1858
 Ancestry.com. Convict Indents, Indian 1810. State Archives NSW; Series: NRS 12188; Item: [4/4004]; Microfiche: 633.
 The Lancaster Gazette and General Advertiser, for Lancashire, Westmorland, etc. (Lancaster, England), Saturday, October 21, 1809; Issue 436. British Library Newspapers, Part II: 1800-1900
 Ancestry.com. Home Office: Convict Prison Hulks: Registers and Letter Books; Class: HO9; Piece: 8
 Sydney 16 December 1810
 Colonial Secretary's Index
 Leicester Journal, and Midland Counties General Advertiser (Leicester, England), Friday, January 08, 1813; pg. 3; Issue 3054. British Library Newspapers.
 Ancestry.com Home Office: Convict Prison Hulks: Registers and Letter Books; Class: HO9; Piece: 4
 Sydney Gazette 24 June 1815
 Ancestry.com. Colonial Secretary's Correspondence. Title: Copies of Letters Sent Within The Colony, 1814-1827.
 Ancestry.com Colonial Secretary's Correspondence. Title: Petitions To The Governor From Convicts For Mitigations of Sentences.