J.S. Mill is considered one of the most influential figures of the classical political economy. In attempting to reconcile Ricardian and non-Ricardian political economy, Mill developed radical views on various matters, including the distribution of wealth and his political economy of small proprietorships. Mill, as an Examiner of the East India Company, was inclined towards defending imperialism and British rule in India. His support for British imperialism aimed at promoting the material and moral improvement of British colonies while, at the same time, he believed that the harm principle sets limits to coercion, as people in India were not savages but enslaved people to despots. This article points out that the Indian land case provides a crucial link to connect Mill’s political economy of small proprietorships with his tolerant imperial political thought. It is argued that this conjunction is necessary to our understanding of Mill’s political economy and political theory.