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Woolloomooloo is the name given to the horseshoe-shaped valley immediately east of the original settlement of Sydney Town. It stretches from William Street down to the harbour, bordered on the west by Sir John Young Crescent and the Domain, and ends abruptly on the east at a high escarpment. Above this cliff face, attainable via several dauntingly long sets of stairs, is Potts Point, earlier known as the Woolloomooloo Heights. The settlement history of Woolloomooloo is tied up with this higher ground, as this tale shall later tell.
The valley was originally drained by the Yurong Creek, which ended in mangroves and mudflats. It was approached via a foot-track around the rim of the valley, which Surveyor Mitchell formed into the Woolloomooloo Road (later William Street) in 1831. But this road could be impassable when the creek ran high, and in addition was a hangout for gangs of thieves ready to take on the unwary traveller heading out of town.
Swampy [media]land that was regularly flooded did not make it especially attractive to early settlers. But it was fertile, and after the colony's commissary-general, John Palmer, was granted land here in 1793, he built a house and made a good fist of farming. The native melaleucas and casuarinas were replaced with fruit trees and he even experimented with growing tobacco. The success of his endeavours resulted in the valley becoming known as The Farm.
Some of the earliest maps label the place Garden Cove, or Garden Island Cove, as it was adjacent to Garden Island, but 1791 recordings of local names assigned Ba-ing-hoe for the island and Walla-mool, Woollamoola or Walla-bah-mulla for the valley. 
Double U double O double L double O M double O L double O
Palmer settled on Woollamoola House as the name of the residence he built beside the creek close to the shore, and eventually the name for the whole area settled down to Woolloomooloo. Palmer's grant extended well into what is now called East Sydney and Darlinghurst, and as late as the 1840s the name Woolloomooloo was applied fairly indiscriminately to these places, as well as to the valley and the heights beyond.
This suburb's impossible-to-spell name has long captured the imagination, and is the subject of many a ditty. Children were encouraged to commit it to memory through spelling rhymes such as:
Near Sydney Town there's a place of renown,
Which is well known to you, it's called Woolloomooloo,
It's easy to say, I know very well,
But Woolloomooloo is not easy to spell.
Double U double O double L double O M double O L double O
Now make that a feature, and I'll be the teacher,
Let everyone here have a go. 
Most just get around the problem by calling it the 'Loo.
The importance of Woolloomooloo to the Gadigal people as a hunting ground and sedentary residential space is referred to in various early records. The place Palmer chose to build on is thought to have been an important Aboriginal ceremonial ground, and though it became a centre of fashionable entertaining for the elite of the Sydney community, local Aboriginal people continued to congregate there.
After 1822 Palmer sold out to Edward Riley who was piecing together a huge estate from the valley south into Surry Hills.  He too is said to have accepted Aboriginal people as nightly residents in the areas surrounding the house. The Fig Tree Baths, a natural sheltered swimming place on the northern side of the bay, adjacent to the Domain, was an early bathing place for colonists who wished to relax away from the stresses of the town, and in the first decades of the nineteenth century it was very probably also a place that was shared with the local Gadigal who had used it for centuries.
Setting the tone
In 1826 Governor Ralph Darling chose the area east of the town to create 'a high status area … which would serve as both example and chastisement to the debased populace of Sydney town'.  He made land grants to his colleagues and friends who were required to build grand houses and landscape them to approved standards. The fine houses were built on the elevated Woolloomooloo Heights, appropriately renamed Darlinghurst Heights, but several of the land grants included low land in the valley as well as higher ground on the ridge and at the top of the escarpment.
This lower ground was the first to be subdivided in the 1840s. By then there were also some cottages on the eastern edge of the valley, and the Riley Estate, which had been tied up in litigation ever since Edward Riley blew his brains out with a pistol at Woolloomooloo House in 1825, was also being subdivided. 
With picturesque outlooks and very little industry, Woolloomooloo enjoyed a brief heyday as a desirable address, separate from the grime of the centre of town. George French Angas commented in 1845 that Woolloomooloo was a 'very pretty' place of villas and gardens, and as late as 1872 visiting English novelist Anthony Trollope referred to the 'combined towns of Sydney and Woolloomooloo', adding that the latter was 'much more fashionable'.  But as the name Woolloomooloo was still sometimes used to describe both the valley and the heights it is possible that the finer houses in more favoured parts eclipsed the lowly workers' cottages that were beginning to cover the valley.
On the way down
Woolloomooloo House was demolished to make way for smaller dwellings in the 1850s, and other large places were being turned into boarding houses. When the authorities carried out an extensive house-to-house inspection of the city's worst housing in 1876, they only took a cursory look at Woolloomooloo towards the end of their survey, but they concluded that they should have paid it more attention. They were surprised at the number of dilapidated and unsanitary houses in the area next to the bay that had seen better days – one with the floor boards gone and a ceiling of brown paper, but with remnant oil paintings still on the walls. 
The catalyst for the social decline of Woolloomooloo was the expansion of the wharfage. There had been some small-scale maritime activities along the bay since the 1820s, but things got much more serious when the mangrove swamps were drained in the 1850s and a new semi-circular wharf was constructed in 1866. Behind the new Cowper Wharf Road there was now space for several new streets, and over the next few decades the area became crowded with small houses, pubs, brothels and billiard rooms servicing a maritime-focussed population.
The Plunkett Street School was opened in 1855, and by 1858 the ferry service from Circular Quay to Cremorne called in on Sundays. Once the Cowper Wharf was operating, there was a regular ferry service on the Watsons Bay run, and this operated until 1924.
Cowper Wharf was used by small coastal shippers, particularly timber traders, and so the adjoining land became dotted with sawmills and timber yards and small-time boatbuilding. It was also the centre of Sydney's fishing trade, with the catch coming from the coastal waters north and south of Sydney, as well as from places closer to home such as La Perouse.
At first the fish were washed in the filthy water of the bay near a major sewer outlet, and sold directly from the wharf until 1872, when the city council built a fine fishmarket at the corner of Plunkett and Bourke Streets. This building served the fish trade until it was sold in 1911, and operations moved away from Woolloomooloo. But from the 1870s fisher folk had moved into the area, including a small community of Maltese and Italian families. This historic connection was reinforced by the arrival of immigrants from Mediterranean countries after World War II. There are still many people in Sydney who remember the fishing nets spread out in the back streets of Woolloomooloo for drying or mending, and for many years until it moved to Darling Harbour in 1988, a blessing of the fleet ceremony was carried on in Woolloomooloo Bay in old Sicilian tradition.
Reputation in tatters
By the late nineteenth century, any good reputation that Woolloomooloo may have had was completely in tatters. Innocent bystanders could be terrorised by the larrikins of the Plunkett Street Push. Fights at the fishmarkets and in the pubs around the wharf were daily occurrences, and landlords were not inclined to bother with maintaining properties which were commanding only small rents. There was a nice irony in the fact that many of the streets in Woolloomooloo were named for judges and other legal worthies in the early colony.
On the hill above the valley, next to Hyde Park, stands the great St Mary's Cathedral. The road that runs down from the cathedral into the 'Loo is called Cathedral Street, but there was a time when it was called Woolloomooloo Street. By the early twentieth century the name of Woolloomooloo was so 'on the nose' that residents petitioned the city council to have the name changed. Fortunately, a similar request to the state government to alter the name of the whole area to St Kilda was refused. This name belonged to a large building on Cathedral Street which would later become an early victim to forces intending to demolish the run-down suburb in its entirety.
About this time Woolloomooloo got the building that defines it in the minds of many Sydneysiders. The Sydney Harbour Trust was established in 1901 with a brief to resume privately run properties all around Sydney's waterfront, and to build modern facilities. Between 1911 and 1915, it built a massive finger wharf at Woolloomooloo that bisected the circular shore wharf. Claimed to be both the largest wooden-piled building and the largest finger wharf in the world, its scale was enormous in the landscape then, and still manages to surprise today. It took overseas shipping from Europe and America as well as from the Pacific. At the same time, non-mercantile shipping grew as the old colonial naval buildings at Garden Island were handed over to the newly formed Australian navy, which settled in and made it its permanent national headquarters. In 1902 soldiers sailed from Woolloomooloo to the Boer War, and from then until the present, troop movements have given the place an air of national importance.
Apart from a plethora of pubs and brothels, there were a handful of public buildings that served other needs of the local population, including Sydney's first day nursery for children of working mothers, established in a small terrace house at 126 Dowling Street in 1905. Later it moved to purpose-built premises in the same street, where it still operates today – as well as in other localities across the city. The organisation is currently known as the Sydney Day Nursery Children's Services. The Royal Blind Society, established at the top of the 'Loo on William Street in 1878, became a landmark, while the tiny St Columbkille's Catholic church, tucked under the lea of the cliff face in McElhone Street, remained known only to a few.
Trams had serviced William Street since the 1890s, and in 1915 the 'Loo got its own tram, which was replaced by a bus service in 1935, though proximity to the city, the shops in Oxford Street, the dives of Kings Cross, the cathedral up the hill or the Domain Baths, meant that residents walked to most places for most of their lives.
The Domain baths were built in 1908 on the site of several other baths at the original Fig Tree Baths location in Woolloomooloo Bay. They became associated with the new sport of swimming and with several world swimming records. Though these feats were not local achievements, locals cheerfully 'owned' them as part of the Woolloomooloo story. The Dom, as they called their pool, has been rebuilt several times, and renamed the Andrew (Boy) Charlton Pool. It remains today, a place in continuous use as a bathing site possibly for thousands of years.
The stories of the middle decades of the twentieth century are the same stories of the inner-city localities in general and of the waterfront in particular. There was not enough work, other than irregular and heavy labour on the wharves. Housing was crowded with too many children and boarders were taken in to supplement the household finances. Landlords would not get the repairs done. Sly grog traders and dealers in other drugs thrived in a world where pubs were legally shut from 6 pm. It was a world of street gangs and colourful cops, of a good deal of misery and a good deal of community cheerfulness and mutual support.
The end of Woolloomooloo
By the 1960s it was all just about over. The locals probably never knew that planners and developers had assumed for all of the twentieth century that this place would eventually become an extension of the commercial city, as well as a corridor for opening access to the better-heeled eastern suburbs. By the 1960s everyone knew it.
The first sound of battle came in 1955 when the car business that owned St Kilda on Cathedral Street applied to demolish it. This old colonial building had been a school, a hospital and boarding house, and was at this time subdivided into flats. Symbolically it was a battle for homes over motor services for the wealthy. The city council several times refused to permit the demolition, and the owners countered with the kind of behaviour that would become familiar in the next few decades.
It was 'on' around at St Kilda. Overhead floors 'accidentally' came in on still occupied flats, gas and water pipes were 'accidentally' severed. Mamma polished up her old primus and lent it to a lady friend so that she might cook some porridge and stew. Others of us cried 'Halt' as best we could but to no avail. St Kilda came down for an asphalt carpark. 
Several ambitious development proposals for parts of the 'Loo came and went, but in 1967 the State Planning Authority unveiled major plans for a high-rise Woolloomooloo. In the first years of the 1970s, an overhead section of the eastern suburbs railway, first discussed a century before, finally emerged from an underground hole in the Domain, overshadowing the little houses that nudged right up to it. 'Even in poor decrepit Woolloomooloo the thing is a blasphemy', wrote the novelist Ruth Park, but she too assumed that 'the old district has gone too far for resuscitation'. 
The population declined rapidly as people left or were 'encouraged' to leave. In 1971 George Farwell and Jean Johnson recorded the passing of the place in a charming book that told the stories – from John Palmer through Nellie Stewart the singer, the poet Chris Brennan, 'Diamond Kate' Carney, with a diamond in every tooth, Inspector 'Killer' Calwell, to Mrs Honora Wilkinson, one-time secretary to Cardinal Gilroy protesting at recent development proposals. But it was written from the perspective that it was all over, and the book was called Requiem for Woolloomooloo. It was to be proved wrong.
Between 1969 and 1971 Sidney Londish, would-be mega-developer in the basin, had acquired 8.5 acres (3.4 hectares), and had applied to the city council to take over many public streets as well. He proposed a multi-towered redevelopment that would take 30 years to complete. It did not include a residential component. After many council meetings involving many motions and rescission motions, discussed amid angry interjections from the public gallery, approval was finally given in early 1973.
Reinventing the 'Loo
But by now a protracted and fierce battle to save the 'Loo was in full swing. The detail belongs to a more general story of the growth of heritage concerns in the 1970s and of the unique constellation of economic and social forces that resulted in resident action groups uniting with the Builders Labourers Federation, which placed 'green bans' on developments that the residents considered unacceptable. Planners and bureaucrats who had long held firm and immovable assumptions concerning a total redevelopment of Woolloomooloo were knocked sideways by a tsunami of community outrage and a genuine shift in public opinion among the wider Sydney community.
While the story of planning in the 'Loo is long and complicated, for many locals it began in earnest on the morning of Sunday 8 October, 1972, on the corner of Forbes and Cathedral streets, where the Woolloomooloo Resident Action Group (WRAG) was formed. Long-term local resident John Mulvena became president and honorary local Father Edmund Campion, who looked after the congregation at St Columbkille's, was made secretary. Organised resistance began to supplant random anger, and a different idea had been gaining momentum against the redevelopment plans. It involved recognition that between them, the state and federal governments owned quite a lot of land in Woolloomooloo.
At the end of 1972, the federal Whitlam Labor government came to power. One of its pre-election promises was to 'save the 'Loo', and it began working closely with the city council to advance this cause. For the next two years negotiations tick-tacked around various obstacles, with the biggest sticking point being a very reluctant state government.
In the meantime, properties continued to deteriorate and population declined. In 1966 there had been 1,430 houses in Woolloomooloo. A decade on, in 1976, less than 60 per cent of these remained standing, and over half were empty. While much of the high level talk was now about preserving the residential quality of Woolloomooloo, commercial tower blocks were banking up along its southern flank on William Street, and to the west a proposed freeway development was blighting everything in its projected path. Green bans were placed on the whole area in 1974.
Tri-partite agreement at last
Finally, in June 1975, an agreement was signed by the three tiers of government, which aggregated land for medium-density public housing. Land was resumed or bought with federal funding. The federal Whitlam government stands out for its commitment to maintaining traditional housing for workers in inner-city localities, with a concerted buy-up of properties in Emerald Hill in Melbourne, and at Glebe and Woolloomooloo in Sydney. These projects married concern for housing with concern for maintaining heritage building stock, and together they form a highly imaginative chapter in the annals of public housing history in Australia.
Developers went into receivership and into court over compensation claims. Planners returned to their drawing boards. Many residents left for greener pastures, but as renting was widespread in Woolloomooloo, the sale of their houses only meant that the government became the landlord, and they stuck it out as new life was slowly breathed into the place. Eventually about seven acres (2.8 acres) were in public hands. Old housing was restored and sympathetic new infill was constructed, with the last buildings finally completed in the early 1990s. Street closures and landscaping along with new community amenities all contributed to creating a pleasant residential precinct.
Not all of Woolloomooloo was zoned residential, however. The south-west corner which contained the St Vincent de Paul's Matthew Talbot Hostel for homeless men, as well as continuing motor vehicle related industries, kept this precinct unattractive to residential development. The building of the Eastern Distributor took away further housing and helped to isolate the western flank of the 'Loo from the Domain. Contrarily, the collapse of the port of Sydney as a commercial shipping destination made the possibility of new and different housing a possibility.
Into the future
By the 1980s the great finger wharf was disused and in bad repair. The government proposed demolition, but public sentiment was for retention. A green ban was placed on the structure, and public meetings multiplied. Uses canvassed included a museum of work and industry, but the usual Sydney solution of privatising for wealthy residential development won out, and in 1999 Walker Corporation and Multiplex completed a $300 million makeover that created over 300 apartments, a hotel and a marina. Some of the world's wealthy now live on Woolloomooloo Bay, and many others visit to enjoy expensive meals at its waterfront locations. Their presence inevitably places pressure on the land-locked residences currently still used for public housing.
 Anon, 'Vocabulary of the Language of N.S.Wales in the neighbourhood of Sydney (Native and English, but not alphabetical)', MS41645(c), Marsden Collection, School of Oriental and African Languages, University of London, London, c1790
 Warren Fahey, 'The Folklore of Sydney project reveals Woolloomooloo's surprising and colourful history', Australian Folkore Unit, viewed 27 November 2008, http://www.warrenfahey.com/articles/woolloomooloo.html
 Christopher Keating, Surry Hills: The City's Backyard, Hale & Iremonger, Sydney, 1991, pp19–20
 Quoted in Terry Kass, 'The History of Tusculum, 1–3 Manning Street , Potts Point, Heritage Research Study', Sydney 1983, p 3
 Sydney Gazette, 24 February, 1825
 A Trollope, Australia, PD Edwards and RB Joyce (eds), University of Queensland Press, St Lucia QLD, 1967, p 234
 Shirley Fisher (Fitzgerald), 'An Accumulation of Misery?', in Richard Kennedy (ed), Australian Welfare History: Critical Essays, Macmillan, Melbourne, 1982, pp 32–38
 Anon, 'A residents Watch on the 'Loo', in Brenda Humble, Save the 'Loo Now, Inner Sydney Regional Council for Social Development, Sydney, nd, p 2
 Ruth Park, The Companion Guide to Sydney, Collins, Sydney, 1973, pp169–170; Shirley Fitzgerald, Sydney 1842–1992, Hale & Iremonger, 1992, ch 11