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A Privileged Upbringing

Roy Coupland Winn was born on 26 June 1890 into a God-fearing family which was on the rise socially and materially. His parents were William and Janet Winn5 née Shade. They already had three sons. Roy was to be their last child.

Roy’s birth certificate lists his residence as North Waratah, which at that time was part of Mayfield on the outskirts of Newcastle, an area where the well-to-do were buying acreages and building grand homes. During his early years, it is likely his parents were living at Winnonaville, a substantial Victorian house on two acres of land at 15 Kerr Street, and later at Winn Court, a larger Victorian house with wide verandahs and five acres of land on the ridge overlooking paddocks leading down to the Hunter River.

Roy was given Coupland as his middle name as a nod to Harriet, his grandmother on his father’s side who, before her marriage to John Winn6 had been a Coupland from Lincolnshire. Roy described his grandmother Harriet as ‘a Personality’.7 Whenever Harriet came to visit, she would never walk up the path from the front gate, she would gallop. Despite the alcoholism and early death of her husband, Harriet had been instrumental in holding her family together and, from the 1850s, in successfully establishing the first of the many Winn’s drapery stores in Newcastle.


Roy’s father William8 was listed on his birth certificate as a draper aged 41. He called himself ‘a merchant’ but is better described as a canny and energetic businessman with determination and practical ability. With his brother Isaac, he further developed drapery businesses in Newcastle and then moved south to establish and run various enterprises in Sydney. During his time at the helm, Winn’s Ltd was a very successful conglomerate. William was well connected to the movers and shakers of the Sydney Establishment and was regularly cited in newspapers as a well-known figure in the business communities of Newcastle and Sydney.

For sport, William shot targets and won a number of prizes. He was prone to losing his temper when people were foolish but would make an apology afterwards.9 He had a short beard that pricked his grandchildren’s faces when he kissed them.


A staunch Methodist, William set great store by integrity and uprightness and was vehemently against the consumption of alcohol. Vice president of the New South Wales Temperance Alliance, newspapers occasionally referred to him as ‘Wowser Winn’.10 His uncompromising temperance stand may have been reinforced by the alcoholism of his father John, who reportedly fell from his horse when drunk, damaged his skull and eventually died in 1855, aged only 40, suffering such severe mental problems that people thought he had gone mad.11

William had positions of responsibility in Methodist church affairs in Newcastle and later in Sydney. The Winns funded the building of the Mayfield Methodist Church and there is still a Winn Hall in its grounds. William, together with his great friend William Arnott of biscuit company fame, chartered space on a ship to bring New Testaments from England to Sydney in order to spread the gospel. The Winns and the Arnotts maintained a close familial friendship which lasted for three generations.


At William’s funeral in 1929, there were many notables from the Methodist church hierarchy, the YMCA, Salvation Army, as well as a large representation of Winn’s Ltd staff. In his will, William left £200 to the Methodist Foreign Missionary Society and £200 to the British and Foreign Bible Society – not inconsiderable amounts in 1929. William is buried in the Methodist section of Rookwood Cemetery near his mother Harriet.

Janet’s parents were Thomas Shade and Sophia Cameron, who was part of the big Donald Cameron clan centred on Stroud in NSW. Janet12 shared William’s Methodism. According to Roy she had the countenance of a saint, religious emotion was the joy of life itself and the Sermon on the Mount a literal guide for how she conducted herself.13 She was a little dour, believed in self-denial and tried to make others do the same.14 She was quiet and in later life always dressed in black.15


William and Janet had three sons before Roy. The first was William Harold, born in 1883 and always known as Harold. He was eventually the director of Winn’s Ltd in Newcastle. In February 1917, he married Helen (Ellie) McMurtrie from Braeside at Lady Martins Beach, Wolseley Road, Point Piper. They had a daughter, Janet Winn, a widely respected dietitian.16 Harold died at 64 in 1948.

The second son was Gordon Russell, born in 1887. He married Ellie’s sister, Ida McMurtrie, in November 1916 and became managing director of Winn’s Ltd in Sydney. They had a daughter Nora and a baby boy who died young. Their granddaughter is Pru Brewer.

The third son was Stanley Dickson, who was born in 1889. Born deaf, it is likely that Stanley was schooled at the New South Wales Institution for the Deaf, Dumb and Blind established in 1872, the first school and boarding facility for the deaf in Australia. Family lore has it that William supported the institution financially. Stanley could deaf sign but lip-reading was the main method of communication within the family. Stanley married Henrietta (Isabel) Arrell who was not deaf when she met Stanley but became so after an illness. She and Stanley had six children – Stanley, Harry, Edena, Reta, Annesley who was also deaf, and Rodney. Over time, Stan’s family participated less and less often at large family gatherings, probably because of the communication difficulties encountered with large groups.17 Stanley died at 59 after being hit by a car.

Roy was born a year after Stanley. William and Janet also had two other children who died at birth – a sister Jessie Harriet in 1879 and an unnamed boy in 1881, two years before Harold.

In the 1890s, as William moved between businesses in Sydney and Newcastle, he bought himself a mansion in Sydney’s inner west at Concord, possibly in Davidson Ave, with a four-acre orchard set in 20 acres of pasture. This was sold after five years as he needed to return to Newcastle to repair the business that Isaac had been running there, but with less success than was anticipated.



Once William was satisfied he could leave the Newcastle business in the more capable hands of Isaac’s son, also called William, he focused on developing Winn’s Ltd in Sydney and he bought Rockley, a large, gracious, turn-of-the-century house in what was then called Campbell Street on Milsons Point.18 It had extensive views across Sydney Harbour to Garden Island, Circular Quay and the Rocks. The family used the ferries that eventually brought cars between the south and north shores of the harbour.

My father Dick remembered the Milsons Point house well. To his childhood eye, the lounge room was full of marvels brought back from various Winn trips overseas. There were black carved dragon tables and huge Chinese vases, which Dick remembered as being taller than he was and like something out of Ali Baba and the Forty Thieves. There were prizes from William’s target shooting successes, including a fancy clock on the mantlepiece.

My Uncle Murray’s memories of the house were different. He remembered a big woodpile on the east side of the house, an attic from which children were excluded and an ever-present widowed grandmother.19

All of Roy’s children remember assembling at the house for a family lunch every Saturday. A full-time cook and housekeeper regularly produced roast chicken, considered a great delicacy. Betty recalled hot plum pudding and cream desserts.20 The only sour note from Dick’s point of view was the cutlery. The knife handles were of ivory which went brown and shrank with a lot of washing. This resulted in a space opening up between the handle and the blade, which would fill up with a greyish deposit that revolted him.21

William would go down on one knee to say the Grace: ‘For what we are about to receive may the Lord make us truly grateful. Amen.’22 Dick and Murray’s cousin, Janet, remembers that the saying of grace preceded all meals and that prayers were recited after breakfast on Christmas Day, further delaying the giving of presents. Rockley Christmases, she recalls, were not nearly as much fun as those at Point Piper where her McMurtrie grandmother lived.23

I have no information about Roy’s early schooling. In January 1906, aged 15, he started at Sydney Grammar School in College Street in the city, finishing there in December 1909. The school’s archivist could provide little information about Roy’s time at the school, apart from the fact that, after the First World War, he contributed £10 for the school’s war memorial. I know Roy won the Class 4 Greek prize in 1907 and received a copy of Homer’s Odyssey because that is written on the book’s flyleaf. It was an appropriate award as, throughout his life, Roy maintained a keen interest in classical literature.


Roy’s two older brothers, Harold and Gordon, had gone to the bastion of Methodist education, Newington in Stanmore, but there is no record of Roy ever attending the school. One can only speculate why Roy wasn’t enrolled. Dick maintained that the strict religious teachings of Newington would not have suited atheist Roy, that the non-denominational Sydney Grammar School would have been more to his taste. This may well have been true but it flies in the face of Roy’s apparent personal piety as well as his pious upbringing. Dick wrote: ‘His mother wanted him to be a Methodist missionary and when he was seven years old he was taken to stand in church and swear he would never drink alcohol.’24

William and Janet initially had wanted Harold to be a missionary but having come dux of Newington he became interested in teaching as a profession. His parents would not support an alternative career like one in education, so Harold went into the family business instead.25 As Gordon was less academically able and Stanley was deaf, William and Janet appear to have turned their sights on Roy to fulfill their desire for a missionary son.


After completing school, Roy went straight to Sydney University to commence a medical degree. It was 1910 and his initial idea was that on graduation he would go to the South Sea Islands as a medical missionary. According to Men May Rise, he initially fixed on being an ordinary missionary, but later decided he would not do any preaching work at all.26 The philosophical and belief processes involved in this slippage from preaching missionary to medical missionary are unclear, but Roy eventually lost all belief in God, even though he never lost his desire to be of help to others.

Roy gained a number of honours in the various medical examinations.27 He graduated bachelor of medicine and master of surgery in 1915. He was appointed Junior Resident Medical Officer at Royal Prince Alfred Hospital, Sydney.

Photos of Roy during these years show an attractive man, five feet eight inches tall, with black hair, hazel eyes and a piercing gaze. His passport describes him as having a broad forehead, ordinary face, straight nose, round chin and dark complexion.28 He was part of a close-knit family of sons who were integrated into a wider familial network of successful Winn businesses, with all members leading socially conventional lives. The expectation was of a life of comfort, status and privilege, in return for upright and honorable service under the umbrella of a robust conservative Methodism.


5 Janet Winn was known as Jessie

6 John was also known as James or Isaac Winn

7 Winn RC Fragment of a letter unaddressed, undated

8 William Winn 1849-1929

9 Winn RC Letter to Betty 20 February 1961

10 Winn RW Memoirs of Richard (Dick) Winn 2003 p5

11 Death certificate of John Winn who was buried at the Field of Mars Cemetery, Sydney

12 Janet Winn 1845-1938

13 Winn RC Men May Rise p3

14 Winn RC Men May Rise p47

15 Winn Murray personal communication 2008

16 Harold Winn’s daughter, Janet Winn, should not be confused with her grandmother, Janet (Jessie) Winn

17 Winn Janet personal communication 2008

18 Address is now Upper Pitt St, Kirribilli

19 Winn Murray personal communication 2008

20 Ferguson Betty Recollections of Sydney Harbour before the Bridge undated

21 Winn RW Memoirs of Richard (Dick) Winn 2003 p13

22 Ferguson Betty Recollections of Sydney Harbour before the Bridge undated

23 Winn Janet personal communication 2008

24 Winn RW Memoirs of Richard (Dick) Winn 2003 p5

25 Winn Janet personal communication 2008

26 Winn RC Men May Rise p48

27 Sydney Grammar School Issue 213 Sydneian September 1912

28 Passport issued by UK Foreign Office 8 April 1918

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