The second son and namesake was probably born in France in the spring of 1240, where his parents had sought shelter from the king’s wrath following the Churching incident. He and his older brother Henry were presumably with their mother Eleanor in Brindisi, Italy, where she waited for Simon to wrap up his crusading business. The first hint of something not quite right with the younger Simon occurs in 1250, when his father sends Henry and third son Amaury to Robert Grosseteste for an education. No reason was given why Simon fils was passed over, but later events suggest he had little capacity for integrity or reliability.
Simon fils missed the battle of Lewes because he had been captured earlier at Northampton. His cousin Edward, who had knighted him and his brother Henry during friendlier days, would intervene at that time to save him from his captors. After his release, he staked his claim to royalist lands in Sussex, some of which he held after the flight of John Mansel in 1263, others he seized through political pressure. What he couldn’t seize was the royalist stronghold of Pevensey, despite a siege lasting all winter and spring.
He was much more in earnest in pursuing Isabella de Fortibus, a rich widow countess who spurned his advances but seems to have remained on well enough terms with Eleanor de Montfort. His highhanded seizure of a merchant vessel earned him his father’s displeasure, as did the tournament he organized in Dunstable with his brothers. The jingling of so many coins in their saddlebags at the tournament in Northampton did not escape notice, either.
It was the crisis following Edward’s escape that showed how little Simon fils was cut out for leadership. His relieving force took over a month to reach Kenilworth and then without making any provisions for defense. Edward fell upon his men in their sleep, with Simon able to escape with barely a shred of clothing on his back. He managed to regroup and was on the road south to link up with his father when he stopped a few miles north of Evesham to rest and have breakfast. Tradition has it that he arrived only to see his father’s head being paraded off the battlefield on the end of a lance.
Back at Kenilworth, he prevented the garrison from taking revenge out their illustrious prisoner Richard of Cornwall. Securing Richard’s promise to aid his mother, Simon let him go and began negotiations with Edward for the surrender of Kenilworth. He was offered a pensioned exile in return for the castle, but, unable to convince the garrison to go along and probably not trusting Edward to keep his word anyway, he chose to flee to the continent. He returned quietly in 1270 to pray at the graves of his father and brother Henry, then joined up with his younger brother Guy in service under Charles of Anjou.
They were together in Viterbo in 1271 when their cousin Henry of Almain arrived in town. As the older brother and heir, Simon might be expected to have more say in what to do about Henry’s mission. Whether he convinced Guy to kill him or Guy acted out of passionate rage, Simon received his fair share of enmity for the crime. Hiding in the north with his brother, he died that same year at a castle near Sienna, some say cursed to the ends of the earth.