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Henry VIII’s “Ugly” Wife Ended Up Having The Last Laugh

Catherine of Aragon - Henry VIII of England

Negotiations and Considerations

Christina of Milan and Marie de Guise- Wikipedia

During this time, England was in a rather precarious position when it came to its relations with the rest of Europe. As Henry decided to create his own religion in order to get what he wanted, that did not rest well with the devoutly Catholic Europeans. In the eyes of Henry’s advisers the best thing to remedy this situation is to marry Henry off again in order to provide some stability. However this became more of a challenge because they now had to consider even more closely the aspect of religion in this future union.

Despite the fact that his marriage proposals had been declined and the fact he had a habit of disposing of his wives, Henry was still technically one of the most eligible bachelors in Europe. When Henry’s first two choices fell through, his right hand man Thomas Cromwell kicked his bridal search into overdrive. This process in reality was a very tricky one, and Cromwell needed to choose the next queen carefully and strategically. He believed that England needed to align itself with a protestant nation and decided to use this marriage in order to do so.

Henry on the other hand disagreed. His previous three marriages had all been for “love” but ironically enough were all technically Catholic- minus that little bit about divorce. This was another reason why Henry initially chose to pursue Christina of Milan and Marie de Guise. As both women quickly dismissed his proposals, Cromwell now had the ability to convince Henry to consider marriage to his choice for queen, one of the daughters of the Duke of Cleves, Anne or her sister Amalia.

Obviously during the 16th century they didn’t have social media or photography, so how did people see each other if they were miles a part? During this time people depended largely on the work of painters to produce portraits of people, especially those in the upper echelon of society. As Henry was unable to travel and meet all of his potential brides, he sent his court painter Hans Holbein along with his ambassadors to visit these women. In the case of the Cleves sisters, both had portraits made of them that were sent back to the king for his examination. Henry ended up choosing Anne based on this now somewhat infamous portrait, and negotiations then followed fairly quickly.

Once a deal was reached, Anne began the long journey from what is now modern day Germany to England. Anne did not appear to have much say in the negotiations as women often didn’t in these days. Nevertheless, she was shipped off to marry a man twice her age that liked to kill off his wives. As hindsight is always 20/20, it is now clear as day that this proposed marriage was probably a bad idea. This was confirmed upon Anne’s arrival and her awful first time meeting with the king. This meeting actually goes down arguably as one of the one of the worst first time meetings in royal wedding history.

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