Simon's family had royal connections. Henry II's great-grandmother on his father's side had been born a de Montfort. Simon was also a descendant of the Norman dynasty through Henry I. The de Montforts had a habit of marrying wealthy women who could add lands and connections to the family effort. They owned land in both France and England. Simon grew up in France. He achieved some of his earliest military experience in the Albigensian Crusade. Thus, no matter how much Simon was celebrated in later centuries as being a founder of English parliamentary democracy, in his personal life he was a doctrinaire Christian who did not like heretics or Jews. Simon wasn't the eldest son. It wasn't a given that he would inherit his father's Earldom of Leicester. He agreed to give up his rights to his family's land in France, and to wait to succeed another man who had been given the rights to the earldom by Henry III. Then, there was the need for a wife, preferably a wealthy heiress in her own right who could augment his fortunes. Simon set his eye on Joan, Countess of Flanders but the French royal family disliked the idea of a heiress to a powerful, independent county being married to a man whose family was connected on both sides of the Channel. Joan married elsewhere. Simon, meanwhile still seeking his family earldom, had worked his way into the graces of Henry III. His eye fell on Henry's sister Eleanor. She had previously been married to William Marshal, Jr.,2nd Earl of Pembroke. After he died, Eleanor swore a vow of chastity, which she broke by marrying Simon. Their marriage was private, given that Eleanor was a widow and possibly risking excommunication by marrying despite her vows. It would take Simon a trip to Rome, no small feat in those days, and years of red tape to relieve Eleanor of this vow and validate their marriage.
At first, Henry and Simon were getting along. Henry allowed his sister's marriage, formally vested Simon with the Earldom of Leicester, and supported his claims in Rome. Simon was godfather of the future Edward I. Then, family drama got in the way. Simon loaned money to an uncle by marriage of Henry and Eleanor, naming Henry as surety for the loan without Henry III's express permission. Henry lost his Plantagenet cool and berated Simon, accusing him of having seduced Eleanor and leading Henry to agree to the marriage under false pretenses. Simon an Eleanor fled to France to wait out Henry's wrath. Simon went on the Barons' Crusade of 1239, fulfilling an earlier vow to go on Crusade and doubtless hoping to clear up his marriage with the Church. He later joined Henry's forces in fighting against Louis IX of France and the two brothers-in-law made up. Henry's reliance on his personal favorites, and his lack of interest in the grievance of his barons irked Simon, who wanted to go on Crusade again. Henry persuaded him to take the governorship of Gascony, one of the few Plantagenet possessions left on the Continent.
Things simmered between the two men for a few years. The Gascon barons complained the Simon, who could be iron-fisted, was oppressive. A formal hearing cleared him of that charge, but revealed irregularities in the finances. He returned to England and turned his attentions to Parliament, where he became an outspoken critic of the King, something bound to rile Henry. As the King became less and less willing to heed his barons' demands, Simon again left England, but returned in 1263 at the request of his fellow barons. As so often happened, both the King and the barons began mustering an army. The royal army bottled up the barons in London, but not for long. In 1264, Simon led the baronial army to battle at Lewes on May 14, 1264, capturing Henry, Prince Edward, and Henry's brother, Richard of Cornwall.
Henry remained King, but decrees had to be channeled through a council, of which Simon de Montfort was the head and driving force. In 1265, he called a Parliament, Montfort's Parliament, which included, not only elected representatives from each shire or county, but also from each town or borough. This was the second parliament in English history at which elected representatives sat, but the first which included townsmen. It was a good idea, but too far ahead of its time. Barons loyal to Prince Edward soon rose against Simon's rule, and backed the King. The brothers-in-law met at the Battle of Evesham on August 4, 1265. Simon was killed in battle, and his earldom and other English possessions confiscated under attainder. His body was mutilated, head, arms, hands and other parts not necessary to mention were sent to the farthest reaches of the kingdom. Henry III order what was left buried under a tree, not deeming a rebel worthy of burial in consecrated ground.
Simon de Montfort in death became something of an unofficial saint. Pilgrims visited his grave and miracles were reported. He became known as one of the founders of English representative government. Several monuments in Leicester bear his name. A bas-relief plaque with his profile is in the House of Representatives chamber in Washington, D.C.
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