Future Freedom and Freedom of Contract

This essay defends John Stuart Mill’s view that the law’s refusal to enforce self-enslavement contracts is justified on the ground that the ‘principle of freedom cannot require that he [the would-be slave] be free not to be free’. Moreover, the essay argues that a concern for future freedom justifies not only the courts’ approach to self-enslavement contracts, but also the courts’ scrutiny of a number of other ‘autonomy-endangering agreements’, specifically: (a) restrictive covenants, (b) ‘equitable relief’ clauses (clauses specifying specific or injunctive relief) and (c) stipulated damages clauses.