Frederick II of the Hohenstaufen dynasty of German kings, who later became the Holy Roman Emperor, King of Sicily, and King of Jerusalem, has enjoyed a reputation as one of the most remarkable monarchs in Europe. The time of Frederick II covers the transition between the Middle Ages and the Renaissance, and Frederick could not have better embodied that period. He was a man who pushed his empire—and Europe—from the Dark Ages of the Middle Ages to the Enlightenment of the Renaissance. His knowledge of several languages, his understanding of Islam, and his friendship with the rulers of the Middle East during the crusading era made him exceptional for his time. His political and cultural ambitions were enormous, stretching from Sicily through Italy to Germany and Jerusalem. His artistic interests, tolerance of Jews and Muslims, defiance of the Papacy, and aim of creating a new, secular world order made him a legend of his own time. These qualities would have made him today a unique politician in a world still needing a complete understanding of cultures and religions. Born in December 1194, in Jesi, Italy, Frederick was the son of Henry VI and Constance, Queen of Sicily. His mother appointed Pope Innocent III as his guardian, but Frederick dismissed him at fourteen and took charge of his life. He married Constance of Aragon, a widow with claims to several crowns, and began consolidating his power. Frederick aroused strong responses in people, ranging from adoration to rejection. Some scholars depicted him as a man who transcended his time and shared values of religious tolerance, rationalism, and secularism, thus belonging more to our world than his. His superior intellect, passion for knowledge, and bold political moves led contemporaries to nickname him "Stupor Mundi," the wonder of the world. This term was initially used by the 13th-century chronicler Matthew Paris to describe Frederick II. Other scholars, including David Abulafia, a 20th-century historian, began to erase the German mystification of Frederick II. His mother, Constance, brought him to Sicily to be raised as the heir to the Sicilian throne. Sicily at the time housed a mixture of Christians, Arab Muslims, and Muslim converts, with a thriving trade network with the Mediterranean world. Frederick was fortunate to grow up in a multicultural atmosphere that uniquely combined elements of antiquity, Islamic and Jewish wisdom, and Norman realism. The capital, Palermo, was a multi-ethnic city. He did not receive a regular education, but his inquiring mind was eager to learn from everything he saw and heard. Speaking six languages (Latin, Sicilian, Middle German, French, Greek, and Arabic) and meeting people of diverse backgrounds and beliefs, he never abandoned the habit of tolerance he grew up with. His proficiency in Arabic allowed him to converse with scholars from the East and use Arabic sources and knowledge for his famous book on falconry, *De Arte Venandi cum Avibus* (*The Art of Hunting with Birds*), considered the first classic medieval textbook on falconry. Frederick's court at Palermo blended Norman, Arabic, and Jewish elements, showcasing his fascination with various cultures. He was a man of profound intellectual distinction; he kept company with intellectuals and artists and encouraged poetry and the sciences. Furthermore, he sponsored intellectuals and believed in the power of culture by promoting the arts and financially supporting men of learning. Frederick expanded his territories in the northern part of Italy, ruled Sicily, dealt with the Papacy, and tried to fulfill his vow to liberate Jerusalem. The Popes feared he would overrun their territory, which was fenced between his lands in the north and his kingdom (of Sicily) in the south. Frederick had vowed to the Pope at his coronations in 1212 and 1220 to go to Jerusalem but was inclined to postpone until the Italian problems had been resolved. He had already gained Jerusalem in 1225 by marriage to Isabella of Brienne, the heiress to the Kingdom of Jerusalem. Throughout his reign, Frederick had to fight the Papacy. As the successor to the crowns of the Germanic Holy Roman Empire and the Kingdom of Sicily, Pope Innocent III sought to separate Sicily from the Germanic Empire since any ruler possessing both crowns could threaten the Papal States. Frederick spent the following years integrating his rule in Sicily: he broke the resistance of the barons by annulling certain privileges and defeated the rebellious Arabs by resettling them in Apulia, where they could practice religion and self-govern. He then set out to centralize the island's administration by issuing many reforms, fortifying his borders, enlarging his kingdom's harbors, establishing a navy and a fleet of merchant vessels, and instituting measures to bring trade under state control. He reorganized the administration of Sicily and created the civil service, for which officials were trained at the University of Naples, the first university in Europe. Finally, in June 1228, ignoring the ex-communication, Frederick set sail on the Sixth Crusade to the Holy Land, where he successfully negotiated the handover of Jerusalem with the Sultan of Egypt, Al-Kamil, to whom he had previously written: "We did not cross the sea to conquer your country, because we own more countries than any ruler on earth, but to take over the holy places by our contract. You shall have peace from the Christians, and not be compelled to shed the blood of your subjects, against us." Thus, Jerusalem, Nazareth, Sidon, Jaffa, and Bethlehem were relinquished to the Crusaders by peaceful means, which the five earlier crusades had not achieved. Amin Maalouf writes in his book *The Crusades Through Arab Eyes* that Frederick was undoubtedly helped in his diplomatic efforts by his knowledge of Arabic, his unconcealed admiration for Muslim culture, "and that he (Frederick) had nothing but contempt for the barbarous West." Al-Kamil and Frederick had exchanged letters in which "they had discussed the logic of Aristotle, the immortality of the soul, and the genesis of the universe." Frederick was often vilified in pro-papal chronicles of the time and since. Pope Gregory IX even went so far as to call him the Antichrist, while at the same time, Frederick was hailed as a messiah by his admirers. He supported the demand that the church return to the simplicity of the early Christian community. — Dr. Nawal Al-Jubeir is a retired Assistant Professor of German. She was on secondment to the Saudi Cultural Mission in Washington, DC. You can reach out to the author on her email [email protected].