James IV of Scotland
William Sinclair, 2nd Earl of Caithness was killed fighting for James IV of Scotland at the Battle of Flodden in 1513. There was a loss of 300 Sinclairs including George Sinclair of Keiss, Henry Sinclair, 4th Lord Sinclair, Sir John Sinclair of Herdmanston, the Bishop of Caithness as well as James IV of Scotland.