This thesis explores the relationship between legitimacy and inequality in well-established, embedded democracies by considering inequality as a potential cause of legitimacy crises. In the first chapter, the thesis reviews rival accounts of how to conceptualise political legitimacy and of what poses a threat to it. In subsequent chapters, it syncretises these accounts together. The second chapter argues that legitimacy crises are created by resentment, i.e. inability on the part of the subjects themselves to identify with the state’s actions. It also argues that legitimacy crises need not be acute crises in which the regime’s survival is imminently threatened but can instead be chronic crises in which the political debate increasingly focuses on how the state makes decisions rather than merely what decisions it makes. The third chapter discusses how a state that has entered a chronic legitimacy crisis might get out of it. It proposes that resentment is driven by gaps between perceived conditions and expectations, and therefore states can “solve” legitimacy crises by changing the perception of conditions or “settle” them by adjusting expectations. Finally, it argues that solving and settling strategies can feed off each other in a vicious cycle, producing “sinking”, in which resentment persists or worsens. The fourth chapter then applies the model produced in the second and third chapters to inequality, showing how certain forms of inequality can give rise to a chronic crisis and prove intractable enough that they result in sinking.