“Wife-murdering tyrant.” “Gross man-child.” “Obsessive,” “self-indulgent” and “syphilitic.” These are just a few of the insults used to describe King Henry VIII in a new survey conducted by the Historical Writers Association (HWA). Asked to name the worst monarch in history, 20 percent of the more than 60 authors polled chose Henry VIII. Henry, who ruled England from 1509 to 1547 as the second king of the Tudor dynasty, is of course most famous for having six wives—two of whom he had executed—but he also broke with the Catholic Church, started the English Reformation and made himself head of the Church of England, executing pretty much anyone who got in his way. Does that make him history’s worst monarch? We explore some of the most controversial parts of Henry VIII’s reign, and why he may have earned this dubious distinction.

All those wives…
Much of Henry’s bad reputation comes from his eventful (to say the least) marital life. In need of a male heir, he got his marriage to Catherine of Aragon annulled in order to marry the ambitious noblewoman Anne Boleyn, inadvertently starting a revolution in the process. When Anne produced only a daughter as well, Henry had her executed for adultery and treason and immediately married Jane Seymour, who produced the much-desired son, but died in childbirth. His fourth marriage, a political match with Anne of Cleves, lasted only a few days, while number five, Catherine Howard, met the same fate as Anne Boleyn. His last wife, Catherine Parr, outlived Henry. At best, the king’s marriage track record was an object of ridicule; at worst, it made him look like a monster. With all that fuss over a son, it was his daughter with Anne Boleyn who ended up as the longest-reigning Tudor monarch, Queen Elizabeth I. (She was, incidentally, voted history’s best monarch in the HWA poll).

He was constantly taking his country to war—and he wasn’t very good at it.
Though Henry VIII showed little talent as a general, England was constantly at war during his reign, with not much to show for it in the end. His repeated efforts to conquer Scotland ended up pushing that country into an alliance with France against him, while his alliance with Holy Roman Emperor Charles V soured during Henry’s crusade to end his marriage to Catherine of Aragon, the emperor’s aunt. In 1542, Henry and Charles would join forces again to fight France—traditionally England’s chief rival—in what would be the third French war of Henry’s reign. By that point, Henry was too fat to lead his men on horseback; he had to be carried on a litter along the battle lines. Even after Charles signed a treaty with the French, Henry continued the struggle, bankrupting himself in the process. At war’s end, all he had to show for it was the relatively minor port of Boulogne, which would soon be back in French hands anyway.

His messy separation with the Catholic Church—and relentless persecution of those who opposed it.
After years of trying and failing to get his first marriage annulled, Henry turned to wily adviser Thomas Cromwell. In 1532, Cromwell got Parliament to pass a law making Henry the head of the Church of England, effectively removing England from the pope’s authority. Henry’s power increased exponentially over the next decade, as did his wealth: All English monasteries were closed, and their assets transferred to Henry’s coffers. Opponents of the revolution, such as Henry’s old friend and adviser Thomas More, were executed under harsh treason laws.

Executions, executions…and more executions.
In the late 1530s and early ‘40s, Henry had various members of the Pole and Courtenay families executed—supposedly for conspiring against him, but mostly because their royal blood gave them competing claims to the throne. In 1541, he even ordered the execution of the frail 67-year-old Margaret Pole, once his daughter Mary’s governess. Eventually, Thomas Cromwell’s role in arranging the king’s failed marriage with Anne of Cleves would turn Henry against him as well, and he was executed in 1540. In 1547, five years after Catherine Howard’s premarital affairs (and possible adultery during her marriage to Henry) led to her execution, the king had her uncle Henry Howard put to death based on accusations from a rival family in court, the Seymours. The 16th-century historian John Stow claimed Henry had some 70,000 people executed during his reign; though that was an extreme exaggeration, the number surely reached into the hundreds.

He inherited a fortune, and lost it all (and then some).
Henry VIII inherited a large fortune, the equivalent of some £375 million today. But despite the influx of money from the dissolution of the monasteries and new taxes imposed by Cromwell, Henry’s government seemed always to be on the verge of going bankrupt, thanks to his profligate spending. Presenting the ultimate display of magnificence and power to the world didn’t come cheap—Henry’s court was one of the most lavish in history—not to mention his many expensive continental wars. His inheritance went quickly, and though annual incomes remained steady thanks to rents and dues paid by his subjects, inflation and rising prices made an impact. Twice during his reign (in 1526 and 1539) Henry devalued England’s coinage, which provided temporary relief but ended up making inflation worse. He would die in debt.

A possible explanation?
Some have argued that Henry’s serious injury in a jousting accident in 1536 marked a turning point in his transformation from a relatively generous, benevolent ruler into the “wife-murdering tyrant” many remember. By aggravating existing health problems—including sores on his legs that may have been caused by the restrictive garters he wor—-the accident restricted his movement, causing him to gain weight quickly. (Despite one persistent rumor, there is little evidence to suggest that Henry had syphilis.) His personality also changed, turning from suspicious to downright paranoid. This change, combined with his self-righteousness and absolute power, made Henry very dangerous.

His confused legacy.
By the time he died in 1547, on his 56th birthday, Henry VIII reportedly weighed nearly 400 pounds, and was a very sick, unhappy man. He remained an active ruler until the end, however, and his death left confusion and disorganization in its wake. His young son and successor, King Edward VI, was controlled by his advisers, and his death of tuberculosis in 1553 sparked a succession crisis. After Henry’s daughter Mary I regained the throne from challenger Lady Jane Grey, she spent her five years on the throne trying to bring England back to the Catholic fold. She died in 1558, and it was left to Elizabeth I to restore and solidify her father’s reforms. While not without her own flaws, historians celebrate Elizabeth for keeping England together in a time of bitter religious divisions, a feat that was particularly remarkable given that she was—after all—only a woman.