The Year was 1540

Court painter Hans Holbein had an off-with-your-head mess on his hands. He knew it the instant he laid eyes on sisters Anne and Amalia of Cleves.

Hans Holbein

For once, Holbein’s boss, Henry VIII, was listening to his political advisor and not his heart. As Henry sought Wife 4th, his chamberlain, Thomas Cromwell, warned him, “Look for alliances, not love.” So Henry dutifully sent Holbein off to the Low Countries to paint the two prospective brides. Depending on what they looked like, one sister would become Henry’s new queen.

Amalia de Cleves

Henry’s reputation as a husband wasn’t that great. In fact, a few of his choices had already turned him down. Cromwell was not that popular, either. The son of a blacksmith; he had risen to power as a Church lawyer because he had defended Henry’s right to end to divorce Wife #1.

Anne de Cleves

If Holbein painted the princesses as they were, he might never get to cross the channel with his paintings because their brother, the Duke of Cleves, would likely kill him. If he painted pictures the Duke approved of, Henry would probably kill him when he saw the women. Kill in this sense was literal. Holbein took the middle ground – rather pretty portraits. Henry, 48, chose the older sister, Anne, 24, although her (old) age made him a little wary.

Henry VIII

When Anne arrived in London in January, 1540, Henry grumbled, “She is nothing so fair” as her portrait. Not only was Anne not demure, she had the audacity to beat him at cards. He could not bring himself to consummate the marriage.

By May, everyone agreed on a mysterious pre-existing engagement for Anne, not properly broken. Off went Wife #4 to her own house in the English countryside with a new title: the “King’s Beloved Sister.” And Henry was on the lookout for wife #5.

Catherine Howard

Holbein kept his head, but just barely. The person who lost his head was Thomas Cromwell. Henry had named him Chamberlain on April 17, 1540 and executed on July 18th. That same day, Henry wed Wife #5, the sexy teenager, Catherine Howard.

Holbein died of an infection three years later. Anne, who never married because Henry refused to let her, lived to see the queen who took her place beheaded the day before Valentine’s Day, 1542. Anne of Cleves outlived Henry, too.

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