In 1553 the Edward Bonaventure set sail from England with two other ships to search for a Northeast Passage to Asia. Eventually the ship made it to the White Sea and the captain of the ship, Richard Chancellor, reached Moscow where he met Tsar Ivan IV, ‘the Terrible’, at the Kremlin. In 1554 the ship returned to England but was ‘robbed by Flemings’, according to Richard Hakluyt. The discovery of a case file in the archives of the Great Council of Malines, the supreme court of the Netherlands in the sixteenth century, concerning the robbing of the Edward Bonaventure on its return voyage offers a new perspective on the spectacular first English expedition which resulted in the discovery of the North Cape and Anglo-Russian trade connections and diplomatic relations. Besides offering new knowledge on England’s pioneering voyage of 1553, this article explores possibilities and limitations of case files for historical research and offers a revealing example of political pressure on legal decision-making and shows that legal institutions were not necessarily the puppets of their rulers.