Gonzalo Oleas Zambrano was a socialist lawyer from Quito who, from the 1930s to the 1970s, became deeply involved in assisting rural communities in Ecuador with their legal petitions. Intermediaries have a long and varied history in negotiating relationships between the city and the countryside, and one that is often not well understood. At various points in his career Oleas acted like a tinterillo, a socialist and an indigenista. An examination of Oleas’ petitions quickly breaks down a simplistic characterisation of his actions and interpretation of his motivation. Rather, his ability to transcend existing categories helps explain why rural litigants so often turned to Oleas for assistance.