 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 , being the first Welshman to be made an earl and being 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 Caernarvon Castle , whose architecture carries numerous allusions to the eventual return of a Roman Emperor to Wales . The resulting castle was what historian Anthony Emery has described as one of the " last formidable displays of medieval defensive architecture " . 
