Henry VIII was married more times than any monarch in English history! Being the King’s wife certainly changed each of the women. But how did the women change Henry? And which wife changed him the most…or the most significantly? That’s our debate for Round Five of Monarch Madness. Or should I say Marital Madness? With Henry VIII, marriage was a bit of a mad gamble!

Katharine of Aragon changed Henry by loving him and seeing him at his best and most promising moments. She created a happy marriage and tried to give him a son. She also taught him the essence of disappointment, both in their inability to have a son and in her refusal to accept his desire to annul their marriage. Her determination and stubbornness was an unexpected lesson for Henry.

Anne Boleyn taught Henry to fall, for the first time in his life, head over heels in love. This great love inspires Henry to his “Great Matter.” She also, unfortunately for her, taught Henry he could move on. After spending the first 27 years of his reign with Katherine of Aragon and Anne Boleyn, Henry married four other women in the final eleven years of his reign. Henry had a much easier time envisioning the end of an inconvenient relationship after Anne Boleyn.

Jane Seymour gave him his greatest desire: a healthy legitimate son. This showed the world Henry's dynasty would continue. Having a son and heir was the crowning glory of Henry VIII's reign. Her death devastated him. Jane's impact is evidenced by Henry's including her in his family dynasty portrait and choosing to be buried with her.

Anna of Cleves didn't recognize Henry as King when he dressed as a servant, instead seeing him as an old, unattractive, pushy, unappealing man. He never forgave her. But he also made her the best "get out of jail" offer when he ended their marriage. She had a better relationship with the King after their marriage ended, showing the value of playing nice.

Katheryn Howard first gave Henry an opportunity to regain moments from his younger days. Married to a young bride (possibly as young as 18), Henry was able to pretend he was young again. But he could only achieve this by creating a narrowly defined reality for Katheryn, his rose without a thorn, with no one in her life but him. As her past came forward and disputed his view of her, he became the worst version of himself and executed another wife.

Kateryn Parr was Henry's final wife and offered him a bit of redemption. She supported his children and brought his daughters back to court. She encouraged him to return them to the succession. She was not a nursemaid; instead, she was Regent for him when he went to France and was his companion as he faced his limited future.

All his wives changed him. But which wife changed him most? That’s up to you!! Vote for the wife you think made the greatest difference on possibly history’s worst husband: Henry VIII.

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