Justice Carolyn Simpson had a judicial career spanning a quarter of a century – the longest serving of any of the Supreme Court of New South Wales’ women judges. In this article, we critically examine both the image projected at Justice Simpson’s elevation to the Court in 1994 and the legacy crafted about her upon her retirement. As we move forward into a new century of Australian women in law, these speeches reveal much about women’s changing place within the legal profession, but also demonstrate disappointing continuity in terms of the obstacles faced by women.