The image above shows a glimpse of a Woolloomooloo which is today long gone. The once working wharves are now trendy housing, shops and restaurants, and the plethora of pubs, brothels and squalid homes have disappeared. Once again, Woolloomooloo has transformed into a rather gentrified and popular area for Sydney’s well to do, just as it began life. Yet this very nearly wasn’t the case.

By the mid 20th century, Woolloomooloo’s reputation had been seemingly irrevocably damaged. There was not enough work, houses were overcrowded with a combination of large families and boarders who helped family finances. Homes were badly in need of repair, but most landlords did nothing. Sly grog, drug dealers and criminal gangs were common. It was assumed, by all but those who lived there, that eventually Woolloomooloo would be nothing more than an extension of the commercial heart of the city. Planners and developers had long had plans for the area, and in 1955 the first battle arrived. A car business which owned the old Colonial building, St Kilda, which stood on Cathedral Street, applied to demolish it. There were numerous court battles, and some very shady activities to make St Kilda, which had been transformed into flats, unlivable. Eventually though, St Kilda was demolished to make way for a car park.

In 1967, more major plans were afoot as the State Planning Authority revealed plans to replace Woolloomooloo with high rise buildings. It was assumed by many, even people who were vocal defendants of other areas of the city, like Ruth Park, that Woolloomooloo was too far gone to save. Yet they were wrong. By 1971, Sidney Londish had bought up huge areas of Woolloomooloo and proposed a new development of city tower blocks – none of them residential. The public fiercely protested the plan, but in 1973 council approval was given. Yet it was this proposed development which helped to galvanise the public against the redevelopment of Woolloomooloo. In 1972 the Woolloomooloo Resident Action Group was formed and turned random anger into organised resistance to new development. Then, by the end of 1972 the Whitlam Government, with its election promise to save Woolloomooloo, came to power. The state government was reluctant, but a combination of Green Bans, public opposition and pressure from the Whitlam Government was taking its toll.

In June 1975 an agreement was made at all levels of Government to keep land for public housing and traditional homes for the families who worked in the inner city. Old homes were restored and new homes, which replaced those which were too far gone to save, were built in sympathetic styles. Streets were closed, landscaping and new ammenities were added, transforming Woolloomooloo from a squalid residential area into something which was once again much more gentrified. By the 1980s the finger wharf was in disrepair, and completely unused and although there were again plans for demolition, public sentiment won and eventually the wharves became an expensive residential redevelopment. Today, the juxtaposition of expensive apartment homes and public housing is still common in Woolloomooloo.