Stewart was raised in Drummoyne, in the western suburbs of Sydney. He came from a comfortable lower middle-class background and his father, employed as a health inspector, had a keen interest in Asia. Stewart displayed early promise as a poet after enrolling at Fort Street High School at the age of fifteen in 1932. Before attending Fort Street he studied the trumpet at the Sydney Conservatorium High School. A subtitle honouring Claude Debussy in ‘Prelude: On the Quay,’ written in the last year of high school, demonstrates that music is a formative poetic influence and one which provides a sense of organisation for his later poetry, which is most apparent in the fugue-like thematic structure of his spiritual autobiography By the Old Walls of Kyoto. The reference to Debussy also points to the significant influence the French Symbolists had on shaping the affective Gothic mood of his early poetry.

Fort Street was established in 1850 as an academically selective public high school reserved for intellectually gifted students. He got to know James McAuley at Fort Street and the budding poets shared a common interest in literature which provided the foundation for the exchange of ideas and the opportunity to develop a friendship. McAuley won the school Poetry Prize in 1933, while Stewart achieved the same honour in the two years that follow. In a letter to Michael Heyward, he writes: “Jim and I were not good friends at Fort Street, but rather rivals.” Both poets begin to publish poetry at high school and their rivalry, derived from shared ambition, eventually evolves into an enduring friendship which was always maintain through mutual respect.

He had an early interest in French symbolists Mallarmé and Valéry and provided translations of their work in his first volume of poetry. He also favoured American modernists like Hart Crane and Wallace Stevens. Other major influences include the Romantics poets, especially William Wordsworth and John Keats. Carl Jung was an early metaphysical influence and it was by way of Jung's commentaries on oriental texts that he discovered the 'Traditionalist' school of writers. He also immersed himself in Chinese art and poetry, and this determined the subject matter of his first published collection, Phoenix Wings: Poems 1940-46 (1948). A later volume, Orpheus and Other Poems (1956), was strongly influenced by Jungian ideas.

At Fort Street High School his poetry ranges from scarcely veiled confessional pieces, to poems such as ‘Tanka’ in which he attempts to create maximum distance between himself and his subject matter by importing a foreign posture or manner. The most confessional poems are addressed to a mysterious R.M, whose gender is confirmed by the dedication of ‘Water Images’: R.M. (if he will have it).’ The identity of R.M. has never been established and is a secret Stewart took to his unmarked grave high in the hills of Higashiyama: the mountain range dominating the eastern aspect of Kyoto. Michael Ackland’s biographical research for Damaged Men was unable to confirm the identity of R.M and, as in the case surrounding the mystery of Shakespeare’s Mr W.H., any speculation about his real identity has been inconclusive.

It could be that R.M. is a composite of several different people and deployed in his poetry to explore the emotional terrain of love and loss, assisting him to normalise his personal circumstances and validate his identity as a gay teenager, though much like the debate over the identity of Mr W.H., this is merely speculation and the chance of confirming the identity of R.M. has diminished greatly with the passing of Stewart’s generation. His dedication reveals that his amorous feelings were not always reciprocated as Stewart is unsure “if he will have it.” When he dedicates ‘Estranged’ and ‘Wither Away — ?’ to R.M. in 1933 he does not question his secret lover’s romantic intentions, but by 1934 his outlook changes dramatically. The opening line of ‘Water Images’ informs the reader of the dark journey of separation the subject has travelled: “I have been out and away in the night.” A similar mood, though one which grows persistently darker as time passes, is common to ‘Pansies,’ ‘Tanka’ and ‘Water Images,’ and is characteristic of his high school poetry, especially in his penultimate year. In the opening verse he writes:

when the night air pierces to the heart /and when the prelude of foreboding silence /menaces, /and turns the soul to stone.

The coldness of the night air pierces “to the heart” and as his tender hope fades for the arrival of his friend a menacing silence turns the soul to stone. It is apparent that a better understanding of the correspondence shared by metaphysical agency and subjectivity, much like it is for the French Symbolists, is central to understanding Stewart's poetry. This two-way flow of communication injects his poetry with a spiritual aspect and also demonstrates the structural importance that the philosophical concept of duality has in the inception and construction of his poetic voice.

The frosty autumnal atmosphere of ‘Water Images’ reflects the poet’s state of mind as he realises R.M. would not attend their secret meeting. Overcome with disappointment he borrows lines from the earlier poem ‘Tanka’ and obscures the fact that he has lost his first chance of securing love by creating ambivalence about the gender of his friend (sound familiar as a common gay subterfuge) which is stated in ‘Tanka,’ though in ‘Water Images’ the “he” is replaced with the impersonal pronoun “you.” Concealment occurs after R.M.’s indifference wounds any chance of their nascent relationship maturing to a more secure footing. His willingness to hide the identity of R.M. marks the petitioning of his private life from public view. Whilst the closet door will shield his secret other life and protect him from accusatorial stares and anonymous whispers, the poet must still deal with the emotional pain of rejection. The loss of childhood innocence in the adult game of love is almost palpable in the chiselled lines of the concluding stages when the poet’s mood is eroded by “poignant disappointment” as he accepts that he has been jilted.

Sharp water from the fountains /hyphenate the blue and crystal air /Showered figures there /forever joyful or forever sad /frozen in agony or mirth or stone /wet with drippings like the autumn mountain /when I waited and you never came /when I was sad with an old age /that was my passing youth,/my childhood gone /with the poignant disappointment of the rain /wistful with resignation /warm with tears /wild with the wind /and the rain /in my hair

The raw intensity of youth dissolves like rain as disappointment overwhelms his sensuous mood. A shattered sense of loss distils the dense imagery of the final four lines. The use of enjambment heightens the sense of loss, as if the words themselves are weathered by the raging winds, torn and battered and unable to succeed to their natural end. In ‘Tanka,’ the poet writes about the mountain meeting in the present tense, but in ‘Water Images’ he uses the past tense, haughtily assigning R.M. to the remote cobwebbed corners of memory. With little to affirm, the poet laments his “passing youth” as the elemental forces of wind and rain lash the cathedral of trees and, in a similarly overarching mood, he reminisces about the lost spirit of his innocence. His “poignant disappointment” is an admission that the desire for union did not come to fruition. Regrets arising from unrequited love fuel a plaintive cry, creating an elegiac mood of defeat and sadness. ‘Tanka’ is credited to Skald, one of the poet’s pseudonyms and a persona he deploys as a mask for identity.

Harold Stewart’s enrolment in a teaching course at Sydney University is abandoned before his sophomore year for the less certain but more enticing career of a poet. “I found the courses . . . arid and boring to distraction,” he recalls. His ambition to become a poet gathers momentum during high school and after completing his final year, and without university or full-time employment as a distraction, he embarks upon his chosen career path, spending many hours at the Sydney Public Library copying his favourite poems in long hand. In a letter to Michael Heyward, he writes: “The period between leaving Sydney University and joining the Army was that period during which I worked through many modern influences, getting lost in the wilderness, stuck up blind alleys, and finding my way out of them.”

This period serves as an apprenticeship of sorts, suiting his introspective personality, though he does not abandon his social life completely and continues to gather with university friends in coffee shops and bars around Sydney to discuss literature and listen as they read their latest works. Despite his reserved social demeanour, and without the spur of alcohol as he rarely drinks, he appears forthcoming in conversation, though he has good reason to guard against revealing the more libertine details of his personal life. In a letter to Michael Heyward, Stewart discusses this social life:". . . back in the later 1930’s, I had met Alec Hope and he along with Jim [McAuley] and other literary friends used to meet on Saturday afternoons at Sherry’s Coffee Shop in Pitt Street Sydney to discuss literary topics and improvise light verse, usually of a satirical nature."

While his former classmates engage his intellect and wit, he had other friends entertaining more than just his mind. He refrained from publicly disclosing his sexuality while alive. After his death Cassandra Pybus announces it The Devil and James McAuley and Michael Ackland reiterates it in Damaged Men, though Sasha Soldatow is the first to publish the secret about Stewart’s private life in 1996. Most of his friends were aware that Stewart made his way to the bohemian inner suburb of Kings Cross to discuss modern art, though, at the time, many were probably unaware that he also went there to pursue sexual relations with artists William Dobell and Donald Friend. Discretion about his sexuality is exercised after the final years of high school when accusations about his sexual orientation are made, forcing him to shelter his private life from scrutiny by developing a poetic persona as his public face. It is within this environment of intolerance that he had to appear as if poetry, not marriage and raising a family, is his main priority.

The long reign of Queen Victoria ended at the beginning of the twentieth century but the morality of her times lingered well beyond the 1930’s and dictated that acting out homosexual passions would have destructive consequences. The fate of Oscar Wilde provided a rebarbative lesson to those brave enough to test the boundaries of socially acceptable sexual behaviour and even a poet with the most adamantine reputation, such as A.H. Auden, would not risk coming out of the closet in fear of reprisals. By creating a poetic persona as his public face Stewart could avoid suspicion, though not the fear of knowing that just one probing question could surgically pierce the protective epidermis created by duplicity and expose the rawness of his double life. For many of his friends he is a struggling poet, much like the persona he would invent for Ern Malley in the following decade, but for others he assumes a more furtive role. The avuncular poetic persona he invents for his university friends is not his first mask, nor would it be his last, but just another in a long charade of false identities.

Whether shielded behind the closet door or obscured by a poetic mask, Stewart deflects censure by not courting controversy and avoids offending mainstream sensibilities, more like Auden in this respect than Wilde, though keeping dirty secrets in the small social circles of Sydney required the vigilance of a sentinel.

Long before his conscription to the Army for WWII, Stewart fought a personal war of hide and seek. To understand his diffidence about revealing his sexuality it is necessary to appreciate the historical context of his times. Gay Rights did not exist until it entered mainstream political discourse with the sexual liberation of the 1960’s. Yet, perhaps more tellingly, it must be remembered that Australians were once far less tolerant of those who did not conform to conventional standards and many homosexuals suffered violence and hatred if the truth was revealed. Silence was necessary for survival.

There appears to be a long way to go before either side can claim victory in the battle against marginalising those people who deviate from hegemonic convention, but significant progress has been made since the less pluralistic notions of Stewart's early years shaped opinions and excluded those who were perceived as "different."

During the Second World War, he worked in Army Intelligence (DORCA) at the St Kilda Road Barracks in Melbourne. In 1943, while at the Army Barracks, he collaborated with James McAuley and invented Ern Malley, which aimed to expose the excesses of literary modernism. In The Ern Malley Affair, Michael Heyward recounts the events of the hoax when Stewart conspired with friend and fellow poet James McAuley to dupe Max Harris, the young leader of the modernist movement, and his fellow Angry Penguins associates, into believing that Ern’s sister, Ethel, had found an unpublished manuscript while sorting through her brother’s personal belongings after his premature death at the age of twenty-five from the usually non-fatal hyperthyroid condition known as Graves’ disease or more commonly as goiter. A cure for Graves’ disease does not exist but with palliative treatment the symptoms can be ameliorated. Mostly electing to ignore the warning signs of his faltering health, Ern returned to Sydney after a failed romance tested his resolve, but then, just weeks later, died in the care of his sister, leaving his unpublished manuscript for posterity.

The age of his death was contrived to draw parallels with John Keats, a principal poet of the English Romantics, who had passed away at the same age. More tangential clues awaited discovery, some obscure like the reference to Keats, others more obvious as when Ern writes in ‘Sybilline’: “It is necessary to understand / That a poet may not exist,” though none were sufficiently provocative to prick the ear of suspicion, which was largely due to the credibility of Ethel. By grounding the story with a sense of humility she plays a pivotal role in securing the bond of trust. Her letters display disarming candour: “It would be a kindness if you would let me know whether you think there is anything in them. I am not a literary person myself and I do not feel that I understand what he wrote, but I feel that I ought to do something about them.” A couple of poems were enclosed with her first letter. The language of ‘Durer: Innsbruck 1495’ stunned Harris, resonating with his modern sensibilities. Even though the other poems might not have been as accomplished, Harris made his mind up with the first flush of enthusiasm and read ‘Durer’ over and over again, convinced that with the right promotion Ern could shine as the next big star in the modern firmament, which, in turn, would assist the promotion of modernism. The neat self-serving circularity of the plan was too delicious to resist.

While McAuley has been widely acknowledged as the main author of the meretricious poems, Ethel Malley, an ordinary suburbian housewife, was primarily the product of Stewart’s imagination, though McAuley and his wife Norma made some minor editorial contributions. Ethel has the warm familiarity of a congenial neighbour living in the type of lower-middle class suburb that Stewart experienced as a child but had since gladly left behind. Yet, in the letters, there is also a glimpse of a darker, more judgmental side to her personality; of a suburban philistine insulated from events in the wider world and dismissive of her brother’s impulsive choices, such as his decision to quit his job in Sydney and relocate to Melbourne. Heyward notes: “Ern Malley mocked the romantic myth of the proletarian artist but Ethel anticipated by a decade that formidable icon of the Australian suburban sensibility, Edna Everage.”

Harris was charged with publishing obscene material though could have avoided an appearance before the Adelaide Magistrates’ Court if he had known about Stewart’s skill for inventing poetic masks, yet this would have cruelly denied future generations the brilliant comedy of that vaudevillian farce. Paul Kane in Australian Poetry, p.142, describes the trial as “an incipient Monty Python skit.” Detective Vogelsang was the chief witness for the prosecution and thought that ‘Night Piece’ was obscene. Under oath he declared: "Apparently someone is shining a torch in the dark, visiting through the park gates. To my mind they were going there for some disapproved motive . . . I have found that people who go into parks at night go there for immoral purposes." He also found the word "incestuous" indecent in ‘Perspective Lovesong’ but admitted he did not know the meaning of the word.

The unsettled life of Ern Malley, made painfully public in Ethel Malley’s correspondence where she describes a young poet battling the machinations of a materialistic modern world in the poverty of war-time rationing, desperate for the soft touch of love, for a moment that would clarify purpose with a salvatory meaning, displays an uncanny parallel to Stewart’s own early life. Ironically, he went on to write poetry which represents such an enlightened moment in much the same unappreciated circumstances suffered by Ern Malley. For Stewart, the Malleys were not only a mask to hide behind, but also a mirror which reflected his own precarious life as a young aspiring poet.

Stewart was partly inspired in the creation of an imaginary poet after attending some lectures given by the Argentinian writer Jorge Luis Borges in Melbourne in 1938, though, more importantly, he had been busy inventing several other poetic identities in his earlier years, including Skald and Dulchie Renshaw. Skald was used to hide the fact that he preferred same-sex relationships. Michael Ackland in Damaged Men explores the effect this had on Stewart's life, which, if Ackland's hypothesis is right, was considerable.

Harris eventually overcame the humiliation of Ern Malley and even managed to capitalise on the celebrity gained from the hoax in his business life, but the resentment directed toward Stewart and McAuley simmered long after the last Japanese soldier had surrendered in the Pacific. Serious reservations persisted about the lack of support his poetry received from Australian critics and in a letter to Heyward he outlines his feelings about the lack of critical attention."How would you feel if a life time’s serious work in poetry and prose, based on scholarship and experience of a profound Tradition, were almost totally ignored, while an afternoon’s jen d’espirit by two bored young soldier poets amusing themselves by satirising the fashionable literary kitsch of the period is inflated into an event of national cultural importance?"

His defensive tone highlights the distant relationship he had with his home country and confirms the disregard he harboured for those Australian critics who ignored the later part of his career. The sad and unforgiving truth for Stewart is that Ern Malley not only haunted his career but also eclipsed his other poetry, though this should not be the manner in which his Buddhist poetry is remembered according to several critics. Heyward describes his poetry as “gorgeous, adjectival, multi-faceted like cut jewels, sculpted into tableaux and set pieces.” H.M. Green describes Stewart as an accomplished verbal artist and an innovator in rhythm. In relation to his Buddhist poetry, Dorothy Green writes: “. . . the verse rises to a solemn incantatory splendour quite unparalleled in verse written by an Australian.” A.D. Hope was the first critic to acknowledge Stewart’s skill in marrying Eastern philosophies with the Western narrative form. He writes:This is not chinoiserie, it is not English poetry in Chinese fancy dress. It is English poetry which has enlarged its resources by an intellectual penetration of and an artistic comprehension of another culture. . . I am struck by the mastery, the justice and the originality of movement."Similarly, Kelvin Lancaster, in 1949, argues that even though Stewart appears derivative, excoriating him for adopting the “irresponsible style of Rimbaud,” his poetry provides an original and distinct contribution to Australian poetry: "As it is, his brilliant style and versatile direction are a distinct contribution toward brightening the too often pallid and anaemic style of Australian poetry. With an originality of thought equal to his powers of expression, Mr Stewart could become the major Australian poet of the younger generation." Stewart was sixty-three years old and obviously excluded from claiming to be part the younger generation when his youthful promise belatedly reached its potential with the publication of By the Old Walls of Kyoto in 1981.

During the 1950s he worked at specialist bookshop in Melbourne, the Norman Robb Bookshop in Little Collins Street, and collected many of the Eastern books he would subsequently take to Japan. Many of these books are now currently for sale online after his nephew sold the collection. Noel Tovey in Little Black Bastard provides a brief portrait of Stewart when both men lived in Melbourne, though Tovey's chronology of events is dubious as he states Stewart had recently returned from Kyoto. Stewart's first visit to Japan, however, was in 1961 and not during the 1950s as Tovey states. Given Tovey would have been fifteen or sixteen at the time, it implies Stewart was a paedophile, which was never the case and demonstrates how dangerous it is for reputation when hazy memory parades as biographical fact. Peter Kelly's Buddha in A Bookshop does more justice to Stewart's legacy in both its accurate portrayal of him as a person and the chronology of events. At this stage he begins to move away from the Traditionalist writers he had been studying and increasingly pursues Japanese Buddhism and researching haiku. He published two haiku volumes in the 1960s, which, although popular and reprinted for nearly twenty years, have recently been subjected to some excellent technical analysis by Greg McLaren, who is one of the first academics to examine Stewart's poetry by way of a dissertation.

He visited Japan in 1961 and then again in 1963 to be ordained as a JodoShin Shu priest only to withdraw at the last minute. It was rumoured he did not want to have his hair shaven. He returned to Australian and later enticed Masaaki, the Japanese man he had fallen in love with, to visit. Masaaki claims to have built the first Japanese-style garden in Australia in the Dandenongs. In 1966 he left Australia to live permanently in Japan. He devoted himself to studying the doctrines of Shin Buddhism to which he had converted. He became an expert on the history of Kyoto and was intimately acquainted with its temples, gardens, palaces and works of art. He became fascinated with Japanese poetry and published two translations of haiku: A Net of Fireflies (1960) and A Chime of Windbells (1969) which proved popular with the reading public.

His 1981 book By the Old Walls of Kyoto consists of twelve poems in rhyming couplets celebrating Kyoto's landmarks and antiquities, and Stewart's own spiritual pilgrimage into Buddhism. The poems are accompanied by a prose commentary.

He also devoted a great deal of time to collaborating with his teachers, Shojun Bando and Hisao Inagaki, in producing English versions of Japanese Buddhist classics such as the Three Pure Land Sutras and the Tannisho.

He died in Kyoto on 7 August 1995 after a short illness. A Shin Buddhist ceremony was conducted for him. For a man who always cried poor, he left a considerable sum of money (about a $1M in Australian Dollars), which was intended to fund the publishing of his last long poem, Autumn Landscape Roll, but the money was not used for this purpose and has never been accounted for. His sister was executor of the will. Just one of the mysteries Stewart left behind. The other significant mystery is: Who was R.M? - the boy who rejected his sexual advances during a mountain-top tryst in high school and then spread the word about Stewart and broke his heart. His high school poetry has homoerotic subject matter, making Stewart the first poet to embrace gay subject matter in Australia. Although, the closetted Stewart would probably be horrified to be labelled Australia's first gay poet. In the 1950's he encrypted his poetry with personal homoerotic subject matter and also added other gay subject matter under the guise of Greek mythology. Stewart remained in the closet for the rest of his life, and after he died Cassandra Pybus publicly declared his sexuality in The Devil and James McAuley, which has a rather lopsided and one-dimensional portrayal of Stewart. However, Sasha Soldatow was the first to publicly announce the truth about Stewart's sexuality in the UTS Review in 1996.

To determine Stewart’s position in Australian poetry purely through the dichotomy of modern and traditional is to ignore his more nuanced position, which is one of both modern and traditional. The treatment of his Asian subject matter is modern but his narrative lyrical style is traditional, even though orthodox critical opinion has often concentrated more on style than substance. It is difficult not to conclude that the marginalisation of his poetry was due to the resentment over Ern Malley and the damage it did to the modernist agenda, though it may have also appeared to critics that Stewart had severed ties with Australia, making him less patriotic and his poetry less Australian, and therefore less worthy of study by Australian students. The circular logic of such an argument has an easy appeal. The reception of Stewart’s Buddhist poetry was also caught between the powerful cross-currents of lingering resentment against the Japanese and a reinvigorated Australian nationalism. The recasting of national identity is an imperative that every generation feels compelled, at least to some degree, to undertake. In the last half of the twentieth century the recasting of national identity provided impetus to build Australian course content into the national curriculum, which worked against popularising poetry, at all levels of institutional education, that did not have allusions to the standard ‘sunburnt country’ motifs, such as windswept gum trees, bounding marsupials, one-legged spear throwing aboriginals and beer drinking bushmen in slouch hats singing a jaunty rendition of ‘Waltzing Matlida’ as a riot of kookaburras provide orchestral support. The tendency toward this type of clichéd and jingoistic nationalism has gradually waned toward the latter part of the twentieth century, or at least has been restricted to the international tourism and domestic beer consumption markets, as a largely urbanised and pluralistic Australian population has sought more visceral motifs. For all his youthful enthusiasm, at least the agenda proposed by Max Harris in the 1940’s insisted upon the internationalisation of Australian standards, which would have surely benefited the critical reception of Stewart’s poetry, the irony of which should be inescapable.