There have been two English Holy Roman Empresses in history. The first was the more famous one, Henry I’s daughter, Matilda, who would end up in a struggle for the English throne with her cousin, King Stephen, during the Anarchy (1135-1154). And then there was Princess Isabella, daughter of King John and younger sister of Henry III.

Isabella had the great misfortune of being born the daughter of one of the worst kings of England and, in my opinion, one of the least sympathetic women of the Middle Ages, Isabella of Angouleme. Their marriage was ill-advised from the get-go, though the future Empress, born at the tail end of her father’s life, in 1214, missed most of the drama. She joined two older brothers, Henry and Richard, in the royal nursery, as well as a sister, Joan. The following year, as their father was forced to sign the Magna Carta, a final child, Eleanor, was born.

John’s death on October 19, 1216 left the throne to the nine-year-old Prince Henry, now Henry III. Her mother remained in England long enough to demand her dower rights, before leaving, in 1217, with Joan, then betrothed to Hugh X, Count of Lusignan. Isabella would never see her again and it’s fair to speculate that given she was only three at their separation, her memories of her parents were negligible.

By 1220 the family found itself in the midst of a scandal when Hugh married the Dowager Queen instead of Joan, a move made all the more incestuous given that the Queen had once been betrothed to Hugh’s father, Hugh IX. Isabella couched her actions to her son and his government as making the best of a bad situation, arguing that Hugh’s advisers were pushing him towards a French alliance against English interest. Queen Isabella, older and of childbearing years (she was around 30), was of more immediate interest. Even if true, the marriage benefited the Dowager Queen since she needed a husband to safeguard her lands in Angouleme, of which she was Countess in her own right.

That left the matter of what to do with Joan. Henry III began negotiating a marriage for her with King Alexander II of Scotland, but in the meantime the English government haggled with her mother over custody of the princess. Isabella’s role in all of this was that her brother had put her forth as compensation to the Scots should Joan not make it back to England in time.

In fact, she did. Joan returned to England in May 1220 after an intervention from the Pope, and she and Alexander were married on June 21, 1221 at York Minster.

Isabella, seven, remained on the marriage market. Over the years, Henry negotiated any number of marriages for his sister, including with the Kings of France and the Romans. In the end, Pope Gregory IX suggested a match between Isabella and the Holy Roman Emperor, Frederick II. Henry agreed to the match, however in order to make up the dowry demanded – to be used to help Frederick fund his Italian wars – he was forced to levy significant taxes, which were unsurprisingly unpopular.

Frederick was 40 at the time of his marriage to Isabella and had an interesting reputation among his peers. Twice widowed, he had first been married at age 14 to the 25-year-old Constance of Aragon. The union resulted in his eldest son and heir, Prince Henry. When Constance died in 1222, he remarried to Yolande of Jerusalem. They had two children, a daughter who died in infancy and a son, Conrad, who lived. Constance died in 1228, having left Frederick a widower for seven years by the time of this third marriage.

He was also an outlier on the European stage. King of the Germans, he had no particular interest in the Germany people. He was a Sicilian through and through and his passions lay in the success of his Italian territories. He was believed to be a bit of a heretic as well, less for espousing non-Catholic views and more for not paying much mind to the sanctity of religion altogether. Whatever stock he didn’t put in the Church, he apparently put in astrology – he refused to consummate his marriage to Isabella until the second night on the advice of his astrologer.

Physically, he was described with:

“The Emperor was covered with red hair, was bald and myopic. Had he been a slave, he would not have fetched 200 dirhams at market.”

His eyes, apparently, were green, “like a serpent.”

Isabella, on the other hand, was 21 and one of the noted beauties of the age thanks to her mother. She departed England within three months of the signing of the marriage agreement and bid her remaining family goodbye. She was greeted by rapturous crowds as she passed through German cities on the way to her new home, escorted by an entourage of English lords and ladies. She met Frederick in Worms in the middle of July where they were duly married and she was crowned queen consort. By all accounts Frederick was well-pleased by his bride – he sent her brother three leopards in England by way of thanks.

A rumor has circulated that shortly after her marriage, Isabella was secluded in a harem of Arab women that Frederick kept and attended to, like the other women, by black eunuchs. This is highly unlikely. What is true is that Isabella was usually kept out of the public eye, however this was due more to custom in the region. Her English attendants were also dismissed, which may have helped spark the gossip – only two were allowed to stay with her, including the woman who had likely been her nursemaid in childhood.

The details of how many times and when Isabella gave birth are muddied, however she likely had at least four children. The two that definitely survived were a son named Henry, born on January 18, 1238, and Margareta, born on December 1, 1241. Through her daughter, Isabella is an ancestor to Queen Victoria’s huband, Prince Albert, and thus all subsequent British monarchs.

What is also true about Isabella’s married life was that her husband kept slaves, at odds with English custom. These slaves made up the base of the royal family’s service and traveled with the court as they moved from castle to castle. Likely, Isabella spent more time with them than she did her husband. Frederick traveled frequently and was often off fighting wars. Isabella usually moved about to stay within a reasonable distance of him and he was known to visit her frequently. By all accounts, it was a relatively happy marriage.

There was some irritation and eyebrows raised when Isabella’s brother, Richard, Earl of Cornwall visited her on his way back from a crusade. She was forbidden from attending the public welcoming ceremony, however that was less due to a restrictive confinement and more to do with the fact she was actually in confinement, given that she was pregnant with Margareta. She and Richard met privately and it would be the last time they saw one another.

Six years after her marriage Isabella died giving birth to Margareta in Apulia, Italy. She is buried in Andria Cathedral.