The prevailing political theory of late medieval England established the wealthiest men as the best able to bear the responsibilities of town governance and protect the common good of the community. Examining three middling towns in Greater East Anglia: Colchester, Ipswich, and Great Yarmouth, this study explores the relationship between the ruling elite and other inhabitants of their towns. Although the ruling elite were distinguished through their wealth and power, they were also active members of their community. Not only did they act to protect the economic and political interests of the community, but they were also invested in their local economies and connected to the other members of their community through legal structures and trust networks. Economic and political circumstances, however, impacted the development of these relationships. Great Yarmouth’s reliance on the highly competitive herring industry created a closely connected ruling elite, whose frequent actions together in defense of the town’s common good along with their regulation of the trade to the benefit of their own self-interests solidified their rule. In contrast, Colchester and Ipswich’s reliance on the cloth industry, which expanded in the late Middle Ages, created a number of opportunities for the ruling elite outside the town resulting in a higher turn over within these towns’ ruling elite. Although they acted to protect the jurisdictional boundaries of the town and were connected to other inhabitants of the town through trust networks, these connections were weaker than in Great Yarmouth. Local circumstances are essential to understanding how late medieval towns were governed.