Vlad Dracula
Finding reliable sources was hard with this one. So much of this story is stoked in folklore!
Sources: https://en.wikipedia.org/wiki/List_of_rulers_of_Wallachia
https://www.youtube.com/watch?v=XebzLcG1BoM
http://www.holyromanempireassociation.com/order-of-the-dragon-Ordo-Draconum.html
https://en.wikipedia.org/wiki/Vlad_the_Impaler
https://www.nbcnews.com/sciencemain/vlad-impaler-real-dracula-was-absolutely-vicious-8c11505315
http://www.executedtoday.com/2010/08/24/1460-amlas-vlad-dracula-impaled/