Henry III and Simon de Montfort were about the same age, in their early twenties, both were unmarried and as far as we know had never an intimate relationship with another up to that point. They became great friends and Henry was closer to Simon than his own brother Richard of Cornwall. In 1235, Simon went to France to engage in some marital intrigues on Henry’s behalf. His reward was his own marriage to Henry’s sister Eleanor in 1238, something which the king took a lot of flak for. Now that Simon was married to a princess, he needed a title fitting to his new status and Henry invested him as the earl of Leicester in February of 1239. He had truly arrived.
Within six months he was fleeing for his life. During the time of Simon’s rise at court, Henry was paying subsidies to the duke of Brittany for his alliance with England. Simon was borrowing money from the duke and when he faced default, he named his new brother-in-law, the king of England, as surety. Henry was expected to cover whatever money he gave the duke that wound up in Simon’s pocket. When Henry learned of the swindle, he exploded and ordered Simon thrown into the Tower. The terrified earl of Leicester got a reprieve just long enough to hop on a boat for France.
It was a humiliating episode for Simon and he still recalled it with bitterness 23 years later (image) when friends tried to reconcile them. Simon was intent on war and launched it six months later. Proponents cite his idealism (desire to make life easier for the working stiff) and detractors his greed (enriching himself and his family), but what’s missing is his long simmering anger towards his benefactor. When Simon emerged victorious at the battle of Lewes, undoubtedly his first words were, ‘Vengeance is mine!’