The Female Orphan School has been referred to as a national heirloom, Sydney's forgotten colonial icon, a jewel and a national treasure, but how much do we know about the original purposes of this building? And should we care? This paper reviews the transformation of this building from orphan school to hospital for the insane to university research centre. The case study data is drawn from historical documents, art works, newspaper reports and interviews with architects and heritage consultants. This material is analyzed using a combination of critical discourse analysis and a theoretical framework developed largely from the work Michel de Certeau. The paper argues that while the building's status as an icon, its importance to the local area and Australia's history is strongly promoted in the press, this appreciation is largely superficial. The paper concludes that the greater significance of the Orphan School that we should seek lies in the ways that the building has been discursively formed to produce a range of ideological representations.