Was one of the great divisive figures of Spanish history a loyal servant betrayed by the king or a vicious schemer who committed regicide twice? Take a look at the life of Álvaro de Luna and judge for yourself.

There are many popular historical figures, but the true darlings of history can be looked at two opposite ways. Was Anne Boleyn an innocent woman, caught up and then killed by a bloodthirsty king or a calculating social assassin whose luck finally ran out? Was Caligula an eccentric but competent emperor maligned by critics who made up outlandish stories about him, or was he a full-on murderous psychopath?

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To this list of these controversial figures, add Álvaro de Luna. This man, born at the end of the 1300s, came from a family of nobles devoted to the kings of Castile. His father had been cup-bearer to king Henry III, and Álvaro himself became a favorite of Henry’s son, Juan II. Exactly what that favorite status involved is up for debate. Some believe they were fast friends. Some believed that the king abdicated all real responsibility to de Luna and knew how much he depended on him.

Rumors that Juan II and de Luna were lovers swirled around the court, and remain credible enough that de Luna is mentioned in queer studies books to this day. Odd details bolster the theory. De Luna’s most outrageous outburst came when Queen Isabel, the king’s second wife, decided unexpectedly to stay the night with the king. De Luna pounded on her door and told her he decided when she could spend private time with the king, and that he could “unmarry” her if she disobeyed him.

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Unmarriage would have been a pretty good deal, considering what happened to Juan’s first wife. Maria of Aragon was a formidable woman. She was a member of the Infantes of Aragon, a group of 15th century noble siblings who grew up to rule most of the Iberian peninsula, in part because they had each other’s backs. Maria’s biggest backer was Leonor of Aragon, the Queen of Portugal. Maria managed to get De Luna thrown out of court, and then an odd thing happened. Both Maria and Leonor, hundreds of miles apart, developed purple swellings all over their bodies, keeled over, and died.

Back de Luna came to the court, and he was as powerful as ever. He was the man who had arranged the marriage of Juan and Isabel, when Juan himself would have preferred another queen—so it was fitting that Isabel was the one who took de Luna down. Another mysterious death at court, this time of the king’s accountant. De Luna was the richest man, next to the king, in the entire kingdom. According to some, those riches had been given to him legitimately from the king—as some of them certainly had been. Other contemporaries, including Isabel, believed that de Luna had been padding his income and had silenced the accountant. Eventually, Isabel’s view won out. De Luna was given a show trial and beheaded. It was customary to tie the condemned man’s hands behind his body. De Luna refused the regular rope, and presented the executioner with a rope made of silk which he had brought for the occasion.

So he definitely had style.

But was he an intriguer, an embezzler, and a murderer? Or was he merely a hard-working minister who took all the pressure off a lazy king, and then took the fall for a crime he didn’t commit? It could go either way. Biographies of de Luna admit that, “purple weals on the body, arms, hands, and face would be compatible with some forms of poisoning,” but state that “other indicators like vomiting and gastric trouble are not recorded.”

What do you think? Hardest working man in the kingdom? Or cold-blooded killer.