Well, leaving aside the many many fictional historical figures (because folks in the Middle Ages LOVED their fanfic), I would have to go with the Chevalier de Bayard.
Known in his own time as the “chevalier sans peur et sans sans reproche.” (The knight without fear and beyond reproach). I wrote about him here, but that short capsule doesn’t really do him credit.
To begin with, he was unstoppable on the battlefield. He was the master of the impossibly successful cavalry charge, including charging up mountains and against Swiss pike in formation, but also completely revamped French infantry from a rabble into a disciplined fighting force. He was so brave that he became a continental celebrity in his own time, having single-handedly held the bridge at Garigliano against 200 Spanish knights and single-handedly saved France from the Holy Roman Empire at Mézières.
He was also, by all accounts, a good-looking, charming, and gallant man who effortlessly turned the heads of men and women both. When he surrendered to Henry VIII and Ludovico Sforza on two different occasions, both men were so bowled over by their mancrushes on him that they let him go without ransom. Was sent to Ferrara to help with the defenses of the city, and ended up staying eight months because both Alphonso d’Este and Lucrezia Borgia pretty much fell in love with him – Bayard would call Lucrezia a “pearl among women” and kept making excuses to visit her. Was wounded in the leg when he led the infantry in person on several assaults before the final successful taking of Brescia. He was quartered in the house of a local noble family, where he was healed by a noblewoman and her two daughters, who sang to him every night. When he was healed up, he refunded the ransom that the family had paid him as dowries for the two daughters.
In short, if I didn’t know he was a real person, I would say that Bayard was a bad Self-Insert.
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