Caldicot was renovated as a royal residence during the late 14th century for Thomas of Woodstock, King Edward III's youngest son, and his child bride Alianore de Bohun. Thomas, whose nephew was King Richard II, was in opposition to Richard's alliance with France. On a trip to London, the King, after riding with Thomas galloped away leaving him to be ambushed by the king's men. He was placed under arrest, shipped to Calais, France and imprisoned. Either to buy time or perhaps due to torture, Thomas gave a confession and shortly afterwards was overpowered by four stewards and strangled. Thus the "noble" King Richard betrayed his own uncle.