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“Seeking Castles in Spain”: Sir Hugh Calveley and the Free Companies Intervention in Iberian Warfare (1366-1369)

“Seeking Castles in Spain”: Sir Hugh Calveley and the Free Companies Intervention in Iberian Warfare (1366-1369)

By L.J. Andrew Villalon

Crusades, Condottieri, Codes, and Cannon: Medieval Warfare Around the Mediterranean, edited by L.J. Andrew Villalon and Donald Kagay (Brill, 2002)

Introduction: In March, 1351, sixty warriors walked onto a field in the Duchy of Brittany; and, at a signal, began to fight.  Half of them, French knights besieging a town, took on an equal number of English defenders, in an encounter lasting for several hours which became known as the Combat of the Thirty.  The French triumphed when one particularly rash Frenchman mounted and charged his horse into the English ranks.  While no more than a minor incident in a sideshow of the Hundred Years War, the Combat was one of those beaux gestes which fired medieval imaginations and brought honor to all involved.  Among the Englishmen said to be present were two young warriors destined to rank with the famous captains of the age or, as one historian has called them, England’s “dogs of war”– Sir Robert Knolles and, the subject of this study, Sir Hugh Calveley.

After a brief overview of Calveley’s career, this article will explore in detail his role in a little known chapter of the Hundred Years War, involving the intervention of France, England, and the so-called “free companies” into Iberian warfare.  The conclusion will look at the results of that intervention and their significance for Calveley.

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