The recent case of Aid/Watch v Commissioner of Taxation has created sea changes in Australia in relation to charitable trusts, and as a result our Antipodean neighbours appear to be blazing trails in the evolution of charitable trusts, whilst at the same time, New Zealand resolutely remains entrenched in the annals of charitable trust history. Can, and indeed should, New Zealand continue this traditional approach, as pressure mounts to explore more liberal interpretations of charitable trusts and political purposes? This article explores the two jurisdictions and considers critically, in light of very recent controversial judgments, the diverging paths being taken by the jurisdictions. Before any analysis of the proposition, there must first be a contextualisation of the legal position of charitable trusts and political purposes.