The Kennedy brothers and their unsuccessful attempt at respectability

Market Square Wollongong, showing the Governor Bourke Hotel (far left), the two storey Queens Hotel, and, far right, The Wollongong Hotel, in the early 1850s. Picture: Wollongong City Libraries


THE Kennedy brothers’ attempts at respectability in Australia seemed to have started off on the right foot.

The three Irishmen, Hugh, John and Richard, built a portfolio of properties, and established a profitable cattle trading business, before their empire came crashing to the ground as a result of criminal activity, alcoholism and financial ruin.

While Hugh established a Wollongong pub, south of Sydney, favoured by the gentry and well-to-do, and John became a successful cattle dealer, only one of the brothers – Richard – kept a relatively ‘clean-nose’, never running foul of the law.

John and Hugh were foundation members of the Wollongong Turf Club, selling horses and cattle by commission. The pair was even able to boast of owning a few place getters during the early years of the Wollongong races. What John and Hugh failed to win though was community respect.

They were shady characters, accused of being cattle rustlers, who had been on the wrong side of the law from a young age, and whose lives both ended mysteriously and tragically. Hugh was also fond of the bottle, and was known to settle his arguments by pulling a knife. Both John and Hugh seemed to be estranged from their wives and were constantly droving cattle between the Southern Highlands the Cumberland Plains and their 50 acres Dapto property.

Their father, Hugh Sen was not the best role model, having in 1812 been convicted of possessing a counterfeit one pound two shillings and nine pence Bank of Ireland note, knowing it to be forged. At the age of 44 he was transported from Ireland to the colony of NSW for 14 years.

A weaver, Hugh Sen. arrived at Port Jackson aboard “The Three Bees” on May 6 1814. He was assigned to various prison work gangs about Parramatta before he was granted his Certificate of Freedom in September 1826.

Hugh Sen was successful in applying for his family to be brought to the Colony in 1821. While his wife remained in Belfast, his children, Hugh, 17, Richard, 10, and Mary, 25, arrived in Sydney Town aboard the “John Bull” in 1821.

The three siblings were reunited with their father and older brother, 30-year-old John – who had been in the colony since he was 25. John was transported to NSW for seven years in 1916 for stealing sheep in Belfast.

While Hugh Sen bought property in Parramatta – where he remained until his death – his three children drifted to the Illawarra. Hugh Sen had by this time fathered two more children to a new wife in Parramatta.

A young Mary Kennedy went to work as a dressmaker for Hercules Watt in Pitt Street Sydney, shortly after she arrived in 1821. She later became his housekeeper and had several children to him out of wedlock, possibly because he was already married to Eleanor Chambers. They finally married in 1833. Mary died in 1836.

Meanwhile a young Hugh Kennedy, with his new wife Elizabeth, whom he had partnered with since about 1830, purchased land in Market Square, Wollongong in 1834. He established a general store, where, among other items, he sold liquor in bulk. Hugh soon found himself in trouble with the law.

When he fronted the newly appointed Police Magistrate William Nairn Gray to answer charges of selling liquor in quantities of less than two gallons in June 1834, there were two pubs trading in Wollongong – George Brown’s Ship Inn and Alexander Elliott’s The Crown.

Police Magistrate Gray had been in the job less than two months when Hugh sat before him to answer a charge of sly grog selling.

At the time Brown was on a crusade to crack down on sly grog selling, and had informed the Chief Constable, Edward Corrigan numerous times of the practice in Wollongong Town.

Constable Corrigan told the Magistrate that Kennedy had escaped conviction for illicitly selling of spirits three times; was once convicted, but later had the conviction quashed. However this time around he didn’t escape justice. Gray convicted and fined him for selling a pint of rum.

The fine was the beginning of several confrontations with the law for Hugh.

The following year in February Hugh was at a meeting at the Crown Inn, on Harbour Street, Wollongong to form the Illawarra Turf Club. He was elected clerk of the course and there began a long association both as a committee members and a race horse owner. Interestingly, he found himself in front of the police magistrate again in May 1836, this time on charges of horse stealing. Again, Hugh was acquitted of the charge.

Hugh began building an inn on what is a vacant parcel of land, opposite Market Square, owned today by the Catholic Church on Market Street Wollongong in 1835. Alexander Stewart wrote in his 1897 reminiscence of the Illawarra that during 1835 Kennedy “brought two allotments on the opposite side of Market-Street. The frontage of these extended from Harbour-Street right up to the Queen’s Hotel. On his ground he also built a public house”.

Hugh decided against hosting his Governor Bourke Hotel, a single storey inn with a veranda slung on the front, at the Market Square, probably due to his previous confrontations with the law, and the license was granted to Cornelius Hoolihan on June 27 1837.

The same year his brother Richard bought 50 acres of land near Dapto, and the three brothers seemed financially sound, with the three contributing generously to the building fund for St Francis Xavier’s Wollongong’s Catholic Church and chapel house. Hugh gave £12, 5 shillings, his brother John £11 and 5 shillings, and Richard a £1. Hugh and Richard’s donations were amongst the highest from Wollongong settlers to the church building fund.

A year after his pub was opened, Hugh, in June 1838, moved into the Governor Bourke Hotel with his wife and three children, aged two, four and seven. The same year his four year old daughter Ann died. Hugh and his family remained as hosts for five years.

The year 1843 was the beginning of the dramatic downfall of Hugh. His brother Richard died at the age of 32 in February, while his father also died less than four weeks later. Hugh had closed the Governor Bourke Hotel and was living on his farm at Dapto, where he was also caring for his dieing brother Richard. The Sydney Morning Herald reported on 18 February 1843:

Mr. Richard Kennedy, for many years a confidential and trustworthy superintendent in the employ of Samuel Terry, Esq., and subsequently in that of Mrs Terry. His funeral was attended, exclusive of pedestrians, by upwards of 170 horsemen, and is supposed to be the most numerous and respectable funeral ever seen in that part of the country, which fully exemplifies the estimation in which deceased was held. His remains were deposited in the family vault of his brother, Mr. Hugh Kennedy, at Wollongong, to whose house the attendants on the funeral returned in procession, and were liberally entertained by the bereaved brother.

Hugh’s father, Hugh Sen. died on March 26, 1843, at his home in Parramatta Street, Parramatta, aged 80 years. He was buried in the graveyard behind the Parramatta Benevolent Asylum.

Hugh’s financial problems worsened and he began selling off the family properties, in Corrimal, Market and Crown Streets. He also advertised the Governor Bourke Hotel at Market Square for rent. He was in debt of over 250 pounds and was declared insolvent in October 1843. It was a rough year for the 39-year-old Irishman.

While Hugh’s financial problems continued through the 1840s, so did his appearances before the Wollongong magistrates. He was found guilty of assault and fined £5 in 1845.

But it was Hugh’s brother John who would face the full brunt of the law when he was found guilty on January 7 1846 of highway robbery on the Bulli Mountain Road and was sentenced to “transportation for life”. John was convicted of assaulting William Carter, with intent to rob him, while armed with a gun and pistol, on the Bulli Mountain Road on October 18 1845.

The incident may have been a pay-back for a robbery on Hugh’s pub in December 1840. William Carter, along with John Millar were accused of receiving two gallons of brandy and two of rum stolen from Hugh’s pub on December 23. Carter and Millar were acquitted because of a lack of evidence in May 1841. The Sydney Morning Herald reported on January 7 1846:

Carter it appeared that he was coming to Sydney on the morning named in the indictment, and at about half past seven o’clock he was leading his horse over the Bulli mountain, when he observed a man, whose face was covered with crape, creeping out of the bush, at some distance from the heels of the horse, with a gun in one hand and a pistol in the other; at the command of this man (who afterwards proved to be the prisoner Kennedy), Carter stopped, and took off his coat, waistcoat, and hat, and after this was proceeding to take off his trousers, but was prevented from doing so by his spurs; Kennedy ordered Carter to sit down on a stump at some distance and take- off his spurs, which he refused to do ; upon observing, however, that the prisoner was getting nearer and nearer, Carter turned to sit down, when the prisoner fired the pistol, and the ball striking Carter on the lip inflicted a slight wound, from which the blood began to flow freely. After the lapse of a minute, during which time the two men stood regarding each other, a struggle was commenced, which lasted for some time with varied success, until Carter, who had succeeded in disencumbering himself from his trousers obtained the mastery, and having torn the mask off the prisoner’s face and re- cognised him, he (Carter) struck him on the head with a pistol ; after this some further struggling took place, during which Carter’s shirt was torn completely from his back, but Kennedy having received some further blows on the head which rendered him insensible, Carter beat him about the legs and arms and left him for dead; after which he mounted his horse and went to Wollongong to give information to the police of what had passed, calling at a place by the way to borrow some clothes. Carter had about £70 in notes about him at the time he was stopped, and at the moment he saw Kennedy approaching he stuffed the notes between the back of the horse and the saddle from which it fell to the ground, shortly afterwards when the animal had moved on for a short distance. According to Carter’s statement, Kennedy was aware that he was going that road, although not certain of his having a large sum of money with him. The evidence of Carter, as to the state in which the prisoner was, was confirmed by the Chief Constable of Illawarra in most of its material points, and the latter witness spoke to having found a hat concealed in the bush at some distance from the scene of the conflict, which hat was known to belong to the prisoner, from the circumstance of its crown being mended by a copybook, written by one of his children. The head dress, said to have been worn by the prisoner, was produced in court, and appeared to be a boy’s cap with a piece of crape pendant from the front of it, and some cow’s hair of a   light colour on either side. The pistol was also proved to have belonged to the prisoner. Mr. Windeyer, in addressing the Jury on the behalf of the prisoner, commented at considerable length upon the evidence of Carter, and pointed out the impossibility of a thing so slight in the structure as the crape mask remaining uninjured, as it then was. He also dwelt upon other points of Carter’s testimony, and proceeded to state the particulars of the affair, according to the account given of it by the prisoner, which was, that they were proceeding towards Sydney together, Kennedy on foot and Carter on horseback, when a dispute arose between them concerning a watch seal, which had been purchased by Carter, and was said to have been formerly stolen from the prisoner’s brother. During the dispute, Kennedy drew a pistol, but did not fire it, and Carter, who carried a gun, immediately struck the prisoner a blow with it, which rendered him insensible, after which he beat him in such a manner as to give rise to a belief even in Carter’s own mind, that Kennedy was dead. Seeing this, and being doubtful how he should account for the dead body, Carter immediately resulted to the scheme of going back to Wollongong with the story of an attempt at robbery, never dreaming that he should be compelled by the prisoner’s surviving, to appear and substantiate his story on oath in open Court. As for the cap and mask, it was, in all probability, part of Carter’s own baggage. A number of witnesses were then called on the part of the prisoner, the first of whom, who was by trade a barber, stated that he had shaved Carter on the day after that on which the affray had taken place, and from the appearance of his lip, had arrived at the conclusion that the sore which appeared there was rather the consequence of some natural breaking out than of a wound inflicted by fire-arms. A second witness, Mr. Hercules Watt, of Sydney, proved that he had been for some time expecting the prisoner in Sydney to settle some business relative to the property of his deceased brother, when the intelligence of this alleged attempt at robbery reached him. A third witness, who was a cab-driver named Hughes, swore that he had formerly sold to Carter some brandy which had been stolen from the stores of Hugh Kennedy, the prisoner’s brother, with his (Hughes’s) knowledge; for this offence Carter had been tried and acquitted, although Hughes appeared as a witness against him on that occasion, and according to the account of the witness, Carter had vowed vengeance against himself and the Kennedys on account of the transaction. Several other witnesses were called, from whose testimony it appeared that the prisoner had borne a very good character up to the time that the present charge was brought against him. His Honor directed the Jury upon points of law, with reference to what circumstances were necessary to constitute such an offence as was charged in the present indictment, leaving it with them to determine from the evidence which they had heard, whether the prisoner was or was not guilty of the crime with which he stood accused. The Jury, after having retired for a few minutes, found the prisoner guilty of an assault, with intent to rob, &c., according to the terms of the information. The prisoner when asked whether he had anything to say why sentence should not be passed upon him, begged for mercy, on account of his family. His HONOR then addressed the prisoner in a very impressive manner, telling him that he should have had regard to the condition of his family before he committed the crime of which he had just been convicted, and dwelling upon the necessity of protecting the public from out- rages of this nature, by visiting the offenders with the full severity of the law ; which, happily for the prisoner, was much milder in its punishments than it had heretofore been, as some time since, such an outrage as this would inevitably have been punished by death. The sentence of the Court was, that the prisoner should be transported for life. The prisoner, on leaving the dock said repeatedly to those around him, “he would rather have been hanged,” and appeared much excited after the delivery of the verdict.

Meanwhile Hugh was forced to sell more land in Corrimal Street, before he also advertised the family’s 50 acres property at Dapto for lease. He continued farming at Dapto, increasingly battling the bottle and his debtors, while providing for his wife and eight children. In December 1851, Hugh was accused of stabbing a drinking mate after leaving the bar of the Illawarra Hotel at Dapto.

John Woodfield, a Dapto bricklayer said he had been drinking at George Brown’s public-house when Hugh left a little before dark. Woodfield said he left Brown’s soon after, and overtook Hugh, who was drunk, a short distance on the other side of the Dapto Church. As he passed him, Woodfield claims he was stabbed twice in the chest with a “sharp instrument. A wounded Woodfield made his way back to Brown’s pub where he was treated.

Chief Constable Davis gave evidence at a police court hearing when he arrested Hugh he denied the stabbing. After the hearing, Hugh was committed for trial at the Court of Quarter Sessions on February 10 1852, for stabbing with intent to do grievous bodily harm. He escaped conviction once again, and was found not guilty. Hugh it seems may have been an intimidating character, who persuaded witnesses not to testify against him. He fronted the Magistrates Bench again in May 1856 after another stabbing incident.

Hugh was accused of assaulting his son-in-law, Michael Gallagher after a drinking session. The Bathurst Free Press and Mining Journal reported on Wednesday May 21 1856 that Hugh was committed to stand his trial at the Quarter Sessions, for having stabbed Michael Gallagher, of Jamberoo.

It appeared from the evidence in this case, that on Friday, the 25th ult., Kennedy and his son-in-law, Michael and James Gallagher, were employed in working a threshing machine; and each having drank immoderately of inebriating liquors, became towards the afternoon very quarrelsome. In a tussle between Kennedy and Gallagher, Kennedy drew a pocket-knife and stabbed Gallagher in the left side. The wound though severe was not dangerous; and immediately after it was inflicted Dr Menzie was brought to dress it. Kennedy was promptly taken into custody by Constable Goddard. The principal witness in this case, for the prosecution, seemed disinclined to criminate Kennedy; however they were coaxed by the bench to affirm enough to warrant his commitment.

Hugh’s intimidation never paid off this time around. Although he pleaded not guilty at the Quarter Sessions later in the month, he didn’t escape conviction. He was found guilty of unlawful wounding and sentenced to imprisonment with hard labour in Parramatta gaol for six months.

After Hugh’s release from prison, it seems he joined up with his notorious brother John once again, where they running cattle between a property by the name of Billabong, about 13km from Marulan on the NSW Southern Highlands and the Illawarra. Hugh remained financial fragile and was still dodging bailiffs. He was living at Jamberoo when debt collectors paid him a visit.

His daughter Mary Gallagher was house-sitting for Hugh in May 1857 when the bailiffs came a knocking. Like her father, Mary also seemed handy with a knife. She was arrested by police for brandishing a carving knife on the bailiff and using “impassioned language”. She was charged with assault.

Hugh’s brother John, meanwhile, was killed in mysterious accident near Marulan. He was 66. The Empire reported on Saturday November 28 1857 that John, a butcher from Wollongong, died after falling from his horse. “One of his sons has claimed the mare on which he was riding, and the effects found on the person of the deceased,” the newspaper reported.

There seems to be some confusion around when Hugh died. Ancestors believe that he died of cirrhosis of the liver, a pauper, on December 6, 1859 in the Parramatta Lunatic Asylum at the age of 60, survived by his wife and seven children.

Another theory, researched by a Wollongong historian, says Hugh died at the age of 75 in 1874. 

Updated 2021

© Copyright Mick Roberts 2013

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Categories: Illawarra Hotels, Publicans

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17 replies

  1. Hello Mick – Huge thanks for your research on the Kennedy family! My partner Peter Kennedy is a descendant of the “notorious” John Kennedy, convict son of Hugh Kennedy Snr also as you noted a convict. Two of John’s sons, the eldest son Hugh and the second youngest son Henry Kennedy headed up to Normanton in Queensland – Hugh was a prospector and was on the Hodgkinson Goldfields at their inception with both sons heading up into Gulf country where they were able to carve out a life that appears to have escaped to an extent from the notoriety of their father and uncles. The rest of John’s children stayed closer to home in New South Wales. Loved the photograph of Hugh’s hotel – had not seen it yet. Wonderful research – TROVE is such a gift… Many thanks, Karen

  2. Hi Mick,
    Many thanks for your welcome and well researched contribution regarding the Kennedy brothers, whom for me you have certainly breathed life into. I am one of Hugh and Elizabeth’s (Betsey) ggg grandsons living in Beechworth Victoria.
    Brian Kennedy

    • My pleasure Brian. It was fun resaerching these colourful pioneers… Glad you enjoyed

    • Brian its been ages since you posted but just connecting again as we are both descended from Hugh and Betsy via their son Samuel. Sam ended up living with his mother in Howlong (I believe a number of their children settled in the area) but eventually moved to Galore near Lochart on the Murrumbidgee. I have a quite detailed booklet, compiled by a second cousin using a lot of the land records, which has a very good family tree and details of early family members. I am in the process of copying and scanning this if you would like a copy. Annie

      • Thank you Mick for putting up this information. The Chief Constable Davis mentioned in the article is my great grandfather so it was interesting to read about life back in the 1800’s. Cheers Kim Archer née Davis

      • Hi Ann, I am currently writing a book about the 1840s Depression in the Illawarra and those who became insolvent. This is to be published by the Illawarra Historical Society. As you know Hugh Kennedy was insolvent in the 1840s. I would like to obtain a copy of the book on the Kennedy clan published by W D Kennedy but the nearest available appears to be either in Canberra or Sydney and the book is out of print. I understand you have a copy. If you are willing to share I am happy to meet any expenses. Thank you for your time from Lorraine Neate

    • Hi Brian,I am also a descendant of Huw and Betsy Kennedy(Bowler).

  3. Mick – Thanks for all the work you have done for the Kennedy clan. I am revisiting your page, which I first discovered in 2013. I am directly descended from Hugh Jnr, and his 10th child Samuel (1851 – 1925/26?), who is my great grandfather (I am sixth generation Kennedy). According to my records, the births of eight of Hugh Jnr’s children are recorded in the records at St Francis Xavier Church in Wollongong. Sam was notorious for trading in horses stolen by Ned Kelly. Kelly proclaims his innocence in the Jerilderie Letter. William (Bill) Kennedy – Samuel’s grandson, published this and other information, including the family tree, in 1994 in a book called Innesfail to Innesfell: A History of a Kennedy Sept in Australia. This book shows Elizabeth, Hugh Jnr’s wife, relocating to Howlong with her youngest children.

    Annie Kennedy

    • Hi Annie, Wonderful to see how many descendants of the Kennedys of Antrim have passed this way. I was wondering if the book you speak of above is available? I would love to get a copy as I am helping my father in law with the Kennedy family history – he is Warren Kennedy, a descendant of John Kennedy, Hugh Jnr’s brother. As most of the extended family stayed down south with a lot of the significant older sites and records there – it is a little trickier from Far North Queensland. Huge thanks, Karen van Harskamp

      • Karen, I have only just come across your reply. Life events seem to have taken over so I hope this still gets to you. There are no copies of available of the book but I could copy and scan it for you. Are you still interested? If so let me know and if you give me an email address I could get it to you. The book has a very detailed family tree, including John’s line. Annie


      Hi Annie, this is a pic of Elizabeth (Betsey Bowler) she is buried in Howlong.
      Regards, Brian Kennedy

    • Hi Annie,my family were from the Howlong district,Huw and Betsy’s daughter Anne married a Gilson and their daughter married Edward Cumming-Ince Gason,they were my grandparents.Elizabeth (Betsy) along with her descendants including my father are all buried in the Howlong cemetery.She was the daughter of James Bowler.

  4. Hi Mick – Is there any way to pass a message (I am happy for my email to be shared directly with her) to Annie Kennedy above to ask about family history at all? If not I understand. Huge thanks, Karen

  5. My ancestor, Neil Kelly and his family are recorded in the 1841 census as working on a property belonging to Hugh Kenedy (sic) at Dapto.

    • Chris hi, I am descended from Hugh Kennedy who took over his brother Richard’s 50 acre property at Dapto in the 1830s. He went bankrupt and lost it in 1843 but somehow got it back a couple of years later. Interestingly, the family moved to Howlong on the Murray after Hugh’s death, after which his son Samuel was later imprisoned in Pentridge for receiving stolen horses from Ned Kelly. Any relation of Ned? Anni

      • Hello Ann, an unexpected email – I’d forgotten I posted it! My ancestor Cornelius (Neil) Kelly arrived aboard the convict ship “Martha” in December 1818. He spent his early years until at least 1838 around Sydney’s lower north shore (now Hunters Hill, Lane Cove area). I’ve been trying to establish why he moved to Dapto and the Kennedy farm. I had a vague working hypothesis that there may have been a link with John Kennedy – if Dapto John Kennedy was the same convict who was also on the Martha. Neil Kelly and family returned to Sydney around 1847 and he died in 1849. I can’t prove it, but I don’t think my convict ancestor ever fully abandoned his criminal ways!

  6. Hi Mick thank you for this history of Wollongong. Would that Chief Constable Davis be John Benjamin? If so he is my great grandfather and I’m looking for as much information as I can get.

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