He was born on 26 February 1771 at Cherry Garden and christened at St. Mary Magdalene, Bermondsey, Southwark, London on 19 March 1771, the son of Robert (a mariner) and Catherine Whitmore. He grew up on the River Thames and at age twenty-one worked as a mariner on the river. The skills he acquired in this line of work probably contributed to his ability later in life to overcome setbacks several times over when he transgressed the law
In 1792 he was accused with two other men, William Pendall and William Glassby of feloniously stealing, thirty fathom of twelve-inch cable valued at 50 shillings. All three were convicted of grand larceny on the testimony of accomplice William Neal - " On Saturday night, the 4th of February, I was in company with the three prisoners, and we all agreed to go down the river, to see what we could get: we rowed to the ship Nelly's bows; we cut the cable with a knife; we then under-run it as close as we could to the anchor, and then we cut it, and made it fast to a boat's stern, and carried it forward to her head, then back to her stern; then we towed it away; I hired the boat; Glassby was with me in the boat; in the other boat were Whitmore and Pendall; they towed us up, and we gave what help we could: on seeing Mr. Climber, we let it go; I let go the slip-rope; then we rowed up a little way, and down again; then Mr. Climber rowed up to us, and told us he would seize the boat; he told us to get out of the boat; we did so, and I went home."
All three were convicted at the Old Bailey on 15th February 1792 and sentenced to 7 years transportation.
Their names are entered in the records of Newgate prison books having been admitted on 23 February 1792. They may not have spent very much time on the prison hulks moored in the river. The ship they were transported on the Royal Admiral, departed England on the 30th May 1792 arriving at Port Jackson on 7 October 1792
In October 1796 in Sydney, Robert Whitmore married Mary Goodall, a convict lass who arrived on the Surprize in 1794 having been convicted at the Old Bailey on 10 April 1793, of highway robbery.
Robert was granted a Certificate of Freedom in 1805 which gave him the ability to work on his own behalf. He found employment on a private schooner, the Governor Hunter, a 35 ton colonial schooner built by Isaac Nichols in Sydney and launched 17th January 1805, however he was soon in trouble again -
In July 1806 he and three others John Bell, Thomas Kenrick and Christian Dyke were convicted by the Bench of Magistrates in Sydney with having excited a mutiny on board the Governor Hunter whereby that vessel was in danger of being taken away. They were sentenced to a flogging and hard labour. The Governor ordered that "all persons concerned in private colonial vessels were required to compel their crew to go on board vessels in the Cove on the morning of 14th July to witness the punishments to be inflicted on the daring offenders, which example it was hoped would prevent future destructive tendencies" 
Robert Whitmore overcame this harsh punishment and by 1811 was in command of the Hawkesbury vessel "Chance". However, he came to the attention of the authorities when he was found to have been stealing from the cargo. He was convicted at the Court of Criminal Jurisdiction - Robert Whitmore late Master of the Chance, Hawkesbury vessel, indicted for having feloniously opened five out of six casks of salted pork, and stealing parts of the contents, the property of Henry Kable and put on board as freight at Sydney to be delivered to Windsor. Sentenced to hard labour for seven years transportation. - 
Mary probably didn't accompany him to Newcastle. She was 42 years of age when she was granted a Certificate of Freedom in 1814.  She was granted an Absolute Pardon in that same year.  According to the convict indents she died at the Hawkesbury on 9 May 1822 aged 51.
Robert was appointed Pilot for Newcastle harbour in 1812. He was piloting the colonial vessel Estramina into the harbour on 25 October 1815 when it ran aground remaining trapped for three hours. The master of the Estramina, Captain Joseph Ross refused to take in coals as part of his return cargo because the vessel had been damaged and was taking more water than usual after the incident.
This probably caused inconvenience at Headquarters as coals were sometimes in short supply.
The Estramina was totally wrecked while attempting to leave the settlement with a valuable cargo for headquarters early in 1816. The location of the wreck can be seen on Lieut. Jeffries map. In February orders were issued for a Court of Enquiry to be held to ascertain whether Mr. Ross, the Commander since October 1814, made the necessary exertions or was guilty of any neglect or improper conduct. He must have been exonerated as later in 1816 he was employed piloting the brig Kangaroo in to and out of the harbour. Lieut. Jeffries of the Kangaroo had considered the Newcastle harbour unsafe to enter such a large vessel as the Kangaroo and when he voiced his concerns in correspondence to Governor Macquarie dated 8 February 1816, Macquarie employed Captain Ross to pilot the vessel into Newcastle
harbour in stead 
In January 1816 Commandant Lieut. Thomas Thompson was urged to 'cause every further possible exertion to be made in order to save whatever may be worth saving from the wreck and in particular coppering and iron work which was of great value and much required' . Robert Whitmore took part in this salvage process and was later rewarded.
On 1 July 1817 James Wallis recommended Robert Whitmore for a favour due to his exertions in salvaging materials - a cable and anchor and other items - from the "Estramina" . He became one of several well-behaved industrious ex-convicts and settlers who were permitted to hold farm land at Patterson Plains 'during the pleasure of the government'. The others being John Reynolds, Benjamin Davis, John Swan, John Tucker junr and Richard Binder.
Convict servants were assigned to Robert at the farm he named Mount Pleasant. Thirty-five acres of his land was cleared and crops raised. A wattle and daub hut and a thatched barn had been built by 1823. There was enough maize and stock (pigs) to deliver to the Magazine at Newcastle on account of debt he owed to government, according to the return of land cleared and other improvements made by settlers at Patterson's Plains
Some of the convicts assigned or employed by Robert Whitmore included:
James Cohen per Guildford 1816
John Lloyd per Lord Sidmouth 1819
John Whittaker who arrived on the Mangles 1822
Michael Connolly per Southworth 1822
Patrick Cunningham per Daphne 1819
Daniel Donovan per Prince Regent 1821
John Fowley per Mangles 1822
In October 1824 one of his assigned servants John Dyson per ship Lord Sidmouth was punished with 50 lashes for breaking and destroying working tools and neglect of work
In May 1825 Bryan Coyle per Prince Regent was sentenced to 50 lashes for being off his master's farm at untimely hours. Coyle was punished with 50 lashes again in September 1825 for using threatening language towards his master
Along with some of the other small settlers mentioned above, Robert Whitmore's land at Patterson Plains had been re-distributed to the Church and School Corporation. Initially an offer to move to equivalent blocks on the Williams River was accepted but when the government failed to keep its promise to clear the blocks as compensation for their cleared blocks at Patterson's Plains, they reclaimed the leases on their land at Paterson. The location of the land on the Williams River can be seen on this map (Section A, no. 60)
Captain Henry Gillman's correspondence in 1824 on behalf of Robert Whitmore reveals some of the circumstances of the re-distribution of land grants :
"Robert Whitman (sic), the occupier of an allotment of reserved land at Patterson's Plains is certainly justified in profferring his claim, enclosed in your letter of the 15th January, to the promise held out to him by Major Morisset in consequence of the instructions dated 16 June 1823 which he had received as Commandant at Newcastle informing him that any small settlers in the three townships of Newcastle who might be inclined to change their residence to the first branch of Hunters River would be allowed to receive each the enlarged grant of one hundred acres and convict labour with the rations from the store equal to the value of any quantity of land they had cleared.
He applied for a lease on an allotment of land in Newcastle in 1824 stating that 'he had been a settler at Patterson's Plains since the time that part of the country was first put in cultivation and had invariably studied to demean himself so as to give satisfaction to the respective Officers in Command at Newcastle.' As he had frequently to go to Newcastle for the purpose of disposing of the produce of his Farm he was anxious to build a house for use while he was there.
In August 1828 he gave notice that he intended to apply to the Supreme Court for letters of Administration to the Estate and effects of the late Thomas Addison
A description of this land is within the Registers of Memorials for Land.....'In 1834 thirty acres of land, being the grant of the late Thomas Addison, deceased, and by him willed to Robert Whitmore and situated lying and being at Patterson's Plains adjoining the grants of Anthony Dwyer and Robert Whitmore having the Paterson River in front and Government and Church land at the back, was transferred to William Peagam Coleman. 
In the 1828 census taken in November he was described as age 64, occupation Farmer at Mr. Pleasant
He was described as a free pauper when he died in Newcastle Hospital aged 74 in November 1837. He was buried at Christchurch burial ground on 26 November 1837
 London Metropolitan Archives; London, England; London Church of England Parish Registers; Reference Number: P71/MMG/009.
 State Records Authority of New South Wales; Kingswood, New South Wales, Australia; Series Name: Register of Certificates of Freedom (Certificates of Emancipation), 5 Feb 1810 - 26 Aug 1814; Series Number: NRS 12208; Archive Roll: 601
 State Records Authority of New South Wales; Kingswood, New South Wales, Australia; Card Index to Letters Received, Colonial Secretary; Reel Number: 774; Roll Number: 1250 .