William's son dropped the Welsh version of his name, calling himself William Herbert. He continued to rise in prominence, supporting the House of York during the War of the Roses, fighting in the Hundred Years War in France but making his fortune from the Gascon wine trade. He was also closely associated with Welsh politics and status; he was the first Welshman to be made an earl and was described by contemporary poets as the "national deliverer" who might achieve Welsh independence. In the 1460s William used his increasing wealth to remodel Raglan on a much grander scale. The symbolism of the castle architecture may have reflected the Welsh family roots: historian Matthew Johnson has suggested that the polygonal towers were possibly designed to imitate those of Caernarfon Castle, whose architecture carries numerous allusions to the eventual return of a Roman Emperor to Wales. Historian Anthony Emery has described the resulting castle as one of the "last formidable displays of medieval defensive architecture".