The power to tax is one of the most basic power to assure state revenues. This article attempts to investigate the interaction between tax and democracy, asserting that the two form an important basis for a fiscal social contract between the state and its subjects. The hypothesis is that taxation is the mechanism for legally taking a part of one’s wealth in return for freedoms/services and that compliance with taxation works best with representation. The article outlines the earliest emergence of democracy and taxation, specifically within New Zealand’s historical landscape. It explores what drives tolerances towards taxation and an overview of taxation in undemocratic states. The article concludes by considering whether, at this time in history, democracy would seem to have a significant bearing, positive or otherwise, on taxation. The author’s ambition is that this analytical paper will serve as a guide for policymakers.