Mary Boleyn – Sister, Harlot, Spy

Mary Boleyn is known as the Other Boleyn Girl, the Great Whore and the Mistress of Kings. She has been written about, portrayed on stage and screen, and there is speculation about her life to this very day. Yet the late Eric Ives, arguably the most knowledgeable person on the subject of the Boleyns since my great aunt Tessie, tells us that what we don’t know about her could fill a book.

So, that got me  wondering. Why would a woman of whom we hear so much leave so little evidence of herself behind? We don’t even know for sure when she was born. Then she spoke to me. I was finishing off a bottle of Dewars and studying her portrait. At least we think it could be her portrait. It probably is. Maybe not.  It could be. But I digress. Anyway, there I was with my Scotch, and all of a sudden, it hit me. Mary Boleyn was a spy. I even spotted some secreted writing in her portrait, but I have not been able to find it since, so stealthy were the clues.



We know that Thomas Boleyn, a ruthless and grasping man, placed his daughters in foreign households. Mary promptly finagled herself into the inner sanctum of the king of France. But while she was under the covers, was she truly under cover? The answer is yes. Mary was engaging in espionage, learning all of Francis’ secrets and passing them on to her ambitious father and uncle, the archetypical villain, Thomas Howard. I know! I know that this seems outlandish because we know that Mary was an empty-headed yet fecund tramp, but that was all part of her ingenious cover.

After a while, Mary was recalled to England and prepared to marry. As the eldest daughter, she might have expected to marry James Butler, and make a nice little life as a countess in Ireland. At least we think she was the eldest. She might not have been. But she probably was. See how far this cloak of uncertainty was drawn over her? Anyway, instead of being shipped as a very attractive if somewhat  dimwitted parcel to Ireland, she married one William Carey. Carey was a bit of a nobody really. Some distant cousin to the king, but hardly the heir to Ormond. So why was she kept in England? So she could continue in her trade, duh!

holbein henry

Mary was situated among the ladies of Katherine of Aragon. There she was in an excellent position to sniff out information that passed between the queen and her Spanish ambassador. At the time, everyone wanted to know what was being said between those two. Henry VIII was a bit of a wanker where the saintly Katherine was concerned, and it did not take long for Mary’s kind heart to go out to her mistress. We know Mary was kind  because she portrayed the virtue “Kindness” in the Chateau Vert pageant. So, caring and fearing for her mistress, Mary tried to help her. She started sleeping with Henry.

Now, we don’t know when the affair started, nor when it ended, or if it was a love affair or a booty call, but we do know that at some point Mary was under cover again. She may even have born the king a couple of kids to complete the ruse. They might be his kids. Probably not. But they could be. Anyway, by this point, Mary was a double agent. She was spying on Katherine and the Spanish and Henry and the English. All this information went straight to her dastardly father and her infamous uncle. And where did they go? To France, of course. Yes, yes, I know she was spying on Francis earlier, but allegiances change. Besides, this is what fits with what little we know.

After Mary’s sister entered the game, things got really tricky. Anne either did not want Mary snooping around or maybe they just didn’t get along, but either way Mary again married some random fellow and got kicked out of court. However, she continued corresponding with Thomas Cromwell, and we all know what kind of guy he was.


Eventually,  the feces hit the rotary oscillator between Henry and the Boleyns. He arrested a few, executed a couple, and just really did a number on them. Where was our dear Mary at the time? You might have guessed it. She was back in France. Calais, actually, the last English possession in France. Which is rather telling in itself, don’t you think? She was not brought back for questioning, nor persecuted in any way. There was still one Boleyn flitting about the queen’s chambers and doing all kinds of secret stuff.  That person was the notorious Jane Boleyn, Lady Rochford. But I am all out of Dewars, so that story must wait for another day.

Jeff “the wiz” Berlin



The Other Boleyn Girl ( both the book and unfortunate movies, which I do not recommend)

Dewars (which I highly recommend)

Whoever painted that portrait that is probably Mary Boleyn

Medieval and Renaissance Espionage For Dummies

My Great Aunt Tessie


Author’s note- As a daring super spy myself, this story was near and dear to my own heart. So much so that the wife has since removed the portrait of Mary from my study, muttering something about an unhealthy obsession.


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