Margaret Douglas was born on October 8th, 1515, and from that day onward she was an underdog up against countless obstacles to happiness. At the time of her birth, Margaret’s mother was trying to flee Scotland for England, while her father had quasi-abandoned them both and was scheming his way around Scotland. I’d suggest checking out my essay on Margaret Tudor for a fuller context, but the basic gist is that: Margaret Tudor was Henry VIII’s sister and the recent widow of dead Scottish King James IV. The elder Margaret had rushed into a wedding with legendary asshole Archibald Douglas, and then ran away from all her Scottish enemies to try and hang out with Henry VIII back in England. Basically, Margaret Douglas was born into a complex web of duplicity and double-crossing and to a set of parents who actively despised one another.
The first two years of Margaret’s baby life were a tug-of-war between her parents and Henry VIII, culminating in her father literally snatching her out of her mother’s arms and running off with her to Scotland. There weren’t child custody arrangements back then, but basically, Archibald got primary custody of her through his grab-and-run strategy. He was a terrible person and an even worse soldier, so when he went off to lose various battles, he left Margaret with her godfather as guardian. And who was her godfather? Oh just a certain notorious Catholic by the name of CARDINAL WOLSEY. If you aren’t familiar with the saga of Anne Boleyn, just know that Wolsey wound up beheaded for not being able to procure Henry VIII a divorce so he could marry Anne. Basically, this was far from a Little Orphan Annie/Daddy Warbucks scenario, and Margaret was probably better off when he got himself killed.
By then, she was fifteen years old, extremely clever and intelligent, and reportedly very beautiful and poised. She was also the niece of Henry VIII who was by then very anxious about not having an heir to the throne. Since she was at this point like third in the line of succession, he sent for Margaret to come and live nearby in London. She joined the household of her cousin Mary (later Queen Mary I) who was about her same age, and they became lifelong friends. When Mary was made illegitimate (as part of Henry’s strategy to marry Anne Boleyn), Margaret bumped up a spot in the “who will inherit the throne” sweepstakes, making her an even more important and influential teenager than her cousin. She was appointed one of the main ladies-in-waiting to Queen Anne Boleyn and was now treated basically like a royal Princess which meant she got great dresses and lots of servants but also meant that Henry got to choose who she would marry for political reasons. Too bad for him, Margaret had other plans in mind.
See the thing is, Margaret had already fallen in love with someone. His name was Thomas Howard and he was just four years older than her — that’s why I think it was true love. Sure, he obviously knew that Margaret might one day be Queen and that might have made her more appealing to him, but it was also extremely dangerous for them to be together which counterintuitively means, I think, it was real love. Why was it dangerous for them to be together? Well, not only was Henry sort of notorious for hating it when people got married without his permission but also Margaret was maybe going to be the Queen. The pair got secretly engaged which is just like swoon, because marriage for love reasons was super rare back then, so you know these two teens were really sincere about this whole thing. But things took a turn for the worse when Anne Boleyn fell out of favour and wound up beheaded, because that meant the whole Boleyn family was now highly unpopular. And as it turns out, Thomas was Anne Boleyn’s (much younger) Uncle.
It was all gorgeous and romantic like the second act of Romeo and Juliet, but then suddenly swung into the third act of Romeo and Juliet when Henry found out about them and threw them both in the Tower of London. What was their crime? LOVE! Basically. Thomas was charged with getting engaged without the King’s consent, and Margaret was not charged but still kept locked up. Perhaps sensing that there was really no happy ending in this for her, Margaret broke things off with Thomas. And then in a Gift of the Magi twist, Thomas got very sick with an old-timey disease and died in jail. Margaret was not only heartbroken but also fell very ill herself. Her mother — Margaret Tudor remember her? Back in Scotland? — wrote a letter pleading Henry to let the younger Margaret out of prison so she could convalesce somewhere else. Henry relented, maybe because Thomas was dead now anyway and also he really needed Margaret alive to be his heir, and so she got sent off to a nunnery to heal up.
Happily for all of us, Margaret not only healed up but also Henry finally decided to release her from imprisonment and she was a free woman again. But then in a good news/bad news scenario, Henry was now worried that Margaret’s claim to the throne might overtake that of his son Edward because of blah blah complicated divorce-related reasons. So he pre-emptively had Margaret named illegitimate, meaning she was no longer Henry’s quasi-heir. But she was still his niece and she was still brilliant and gorgeous, so she got a new gig as lady-in-waiting to his latest Queen, Anne of Cleves. Margaret was given the great honour of being part of the group sent to greet the new Queen when she arrived from Germany. Everything was non-stop chaos, but Margaret was the eye of the storm, keeping her eyes on surviving and coming out of this all with as much power as possible.
Of course, the whole Anne of Cleves marriage was very short-lived, and Henry next chose to marry a very young woman named Catherine Howard. Recognize that surname, Howard? Because indeed, Catherine was a relative of the dearly departed Thomas Howard, which may have stirred up some feelings in Margaret to be constantly surrounded by members of her dead ex-fiance’s family. One of the Howards on the scene was a guy named Sir Charles Howard and wouldn’t you know it, Margaret fell in love with him. She just couldn’t quit those Howard boys! Now, Sir Charles was very high-ranking because his sister was the Queen and Margaret had a technically low status as she was still technically illegitimate. But a bigger issue was that, again, Henry hadn’t been their matchmaker and he freaked out whenever anyone hooked up without his go-ahead. And once again, Margaret was sent to the Tower of London for dating without permission. Margaret was brilliant in so many ways, but her weakness was cute boys, how relatable can you be.
Even though she was Henry’s niece, there were only so many times you could get sent to jail before he got tired of you. Luckily for Margaret, her dirtbag father Archibald was currently enjoying a lot of power in Scotland and was able to use his influence to get Henry to release her. Since Henry wanted an alliance with Scotland, and Archibald was his way in, he knew he had to treat Margaret especially well. So once again, she went straight from prison to being a very high ranking lady-in-waiting, this time to Henry’s sixth wife, Kathryn Parr. Margaret and Kathryn had known each other for years and years, having both hung out around the English court throughout their respective adolescences, so it was actually a pretty sweet gig for her. Margaret was one of the only people invited to attend Henry and Kathryn’s low-key wedding ceremony, which was a huge honour and shows just how important she had become.
But the thing about being a really important woman in this court at this time was that Henry was 100% going to marry her off for political reasons. Sure enough, a Scottish jerk named Matthew Stewart came moonwalking into the palace and said if Henry would let him marry Margaret, he’d provide the King with all his troops and support in the English/Scottish war. Like, Matthew was so opportunistic he was willing to betray his entire country just to marry Margaret and get himself a shot at being King (this was banking on Margaret eventually being named Queen of either England or Scotland). Henry figured he had nothing to lose, and agreed to exchange Margaret to Matthew for some Scottish troops. Uncle of the year, this guy.
Margaret was 29 at this time and maybe just happy to finally be married so Henry would stop throwing her in prison. And as it turned out, these two got along pretty good because what they lacked in romantic love they made up for in RUTHLESS AMBITION. Between their various family backgrounds, had a not-insubstantial claim to become Queen and/or King of England and/or Scotland, and quickly became a power couple. Henry VIII and Kathryn Parr were guests at their wedding, which both Margaret and Matthew appreciated since it made them look extra-important. Pretty quickly, their marriage sorted itself out such that Margaret was in charge of everything and Matthew basically did whatever she told him to. They were a power couple, making power moves, including having their first child a year after the wedding. This son was named Henry, though history knows him more by his title, LORD DARNLEY. (**lightning crashes, the ghost of Mary Queen of Scots appears in the sky, screaming**)
Henry VIII was maybe excessively happy with this pairing. He told Margaret that if his own children died childless, he’d be happy for her children to inherit the throne. Given who he was and what Margaret was like, that was like the nicest thing he could have said to her. AND YET Margaret had no intention of being Henry’s sweet little niece and waiting for her grandkids to maybe one day be King. She wanted for herself and Matthew to get more power like RIGHT AWAY and the best way for her to do that was to leverage the Protestant/Catholic divide currently happening in England and Scotland. As a wedding gift, Henry gave Margaret and Matthew a nice little palace in the countryside, and Margaret used this as a not-so-secret meeting place for all the Catholics who wanted to take over the throne from Henry. Because did I mention Margaret was super Catholic? Because she was, and so was Matthew, and they were keen on Making England Catholic Again. Henry found out about this and, for once, didn’t throw her in jail. But rather, he excluded her and her children from the line of succession, forever, and then he died so there were no takesies-backsies.
Margaret was dealt another big blow when her horrible father made the idiotic decision to disinherit her just because he was mad at Matthew for something. So Margaret was now not eligible to inherit any of her family’s land in Scotland, which sucks for many reasons, but most of all because now she was poor. She took a little road trip in 1550 to hang out with Marie de Guise (the dowager Queen of Scotland) and bitch about how much she hated her father. Marie was like, Girl, I know, and I’m sure they drank some wine and said many honest things about how crap things were being super smart and capable women trapped in a series of ridiculous wars being thrown by impulsive men with half their intelligence. Someone should write a short film about this meeting between the two of them, they’d have had so much to discuss and bond over.
Anyway! Margaret had another son in 1555, who she named Charles, and all she could do was hang out with him and bide her time until she was able to scheme more actively. Things got a bit better when Edward VI died and her old pal Mary I took over as the new Queen. Not only was Mary her cousin and childhood BFF, but she was also Catholic! Mary invited Margaret to come live with her at court, like when they were Princesses together but now in a more grown-up version. Margaret was widely seen as Mary’s likely heir, since she was also Catholic and because Elizabeth was still technically illegitimate and also Protestant. Margaret was doing better than ever before, and it was starting to look like she might finally fulfill her goal of becoming Queen!
But then, as ever, things suddenly took a turn. Mary passed away in 1558 without any children, and named Elizabeth as her heir. Margaret was given the honour of being Chief Mourner at the funeral, but obviously that wasn’t exactly the inheritance she’d been hoping to receive. When the Protestant Elizabeth became Queen, Margaret peaced out of there and headed back to her home in the countryside, which again became the main headquarters for Catholics who wanted to overthrow the monarchy. But Elizabeth knew what her cousin was all about, and sent spies up to keep tabs on what Margaret and the Catholics were up to. Elizabeth also had spies in Scotland reporting back to her what Matthew (who was in Scotland at this point) was doing. When she found out that both Matthew and Margaret were scheming against her, she had Matthew thrown in the Tower of London and placed Margaret under house arrest.
It was during this time that Margaret accepted the question of her own legitimacy meant she could never be Queen. And so she set her hopes on her children, specifically Darnley, specifically in marrying Darnley to Mary Queen of Scots. The combined familial dynasty of Darnley and Mary QofS would mean that they’d be an enormous threat to Elizabeth as possible new King and Queen of Scotland. And if that happened to allow Margaret to take the powerful role of King’s Mother, well, that suit her just fine. After some back and forth and feints and Elizabeth being like, “Hmm maybe I’ll get married…” finally Darnley and Mary got married. In retaliation, Elizabeth threw Margaret back into her home-away-from-home, the Tower of London. By this point, presumably there was a Margaret Douglas suite already prepared with all her favourite toiletries.
BUT THEN!! Darnley got himself blown up, and everybody thought that Mary QofS had been behind it. Margaret for sure thought this, and she quickly switched allegiances to now support Queen Elizabeth. Elizabeth released Margaret from prison, and suddenly these two women teamed up against Mary QofS, who was by then on the run on charges of murder. Mary QofS had also abdicated from being the QofS, leaving her and Darnley’s son James as the new Baby King of Scotland. Margaret herself may not have been a monarch, but because of her scheming, her grandson was now a Baby King! Because a baby couldn’t rule, he needed a regent and Margaret was able to finagle Matthew that sweet gig. Finally, after so many decades of so much scheming, Margaret was again at least power-adjacent. For like five minutes.
After Matthew was killed during an uprising in Scotland, Margaret began to reconsider of Mary QofS had truly been culpable for Darnley’s death. And once the incredibly smart Margaret started thinking this through, she noticed all the clues that pointed toward Mary QofS having been framed for the murder. And all at once, Margaret switched allegiances and decided to support her daughter-in-law — but of course, she couldn’t let Elizabeth know. She played both sides for awhile, gently suggesting to Elizabeth that maybe Mary QofS might not be totally guilty. On her way to visit her grandson, Mary and Darnley’s son James the Baby King of Scotland, Margaret took a detour to go and visit Mary QofS at a mutual friend’s house. While there, Margaret’s son Charles fell in love with their mutual friend’s daughter, and the two crazy teens got married. What a wild coincidence that this was a helpful political alliance for Margaret, what are the odds? You’d almost think she engineered the whole thing and you’d be right, because she totally did.
When Elizabeth found out about this new teen marriage, she flipped the fuck out and — say it with me — sent Margaret to the Tower of London. But somehow Kings and Queens just couldn’t stay mad at Margaret, and Elizabeth released her after a pretty short stay. Margaret’s son Charles and his wife had a baby at around this time, a girl they named Arbella and you had better believe I’ll be writing about her because her story is BONKERS AMAZING. Sadly, Charles himself died shortly after Arbella’s birth. His widow, Elizabeth Cavendish, moved in with Margaret and the two lived together with Baby Arbella, presumably all sitting around scheming about how to ensure that this little girl could one day become Queen of England and Scotland. Margaret was still not doing great financially from the whole disinherited situation, and when she died two years later, she was a pauper. Still, she was given a grand burial in Westminster Abbey, as befits the daughter of a dowager Queen, the cousin of a Queen, and the grandmother of a King. Margaret Douglas was buried in the same grave as her son Charles.
NOTE: Margaret probably just died of various old-timey diseases but there is a persistent rumour that Elizabeth had her poisoned to death. This is because a few days before Margaret died, she’d had dinner with Elizabeth’s on/off toxic boyfriend Robert Dudley, a man already suspected of having murdered some other people so…
As far as I’ve found, the only major biographies of Margaret Douglas are So High a Blood: The Story of Margaret Douglas, the Tudor that Time Forgot by Morgan Ring and The Lost Tudor Princess: The Life of Lady Margaret Douglas by Alison Weir. There hasn’t been any film about her, which is ridiculous because her story has EVERYTHING. Margaret’s only filmic appearance I’m aware of is when she appeared on Reign as the meddling mother-in-law to Mary Queen of Scots.
Margaret herself was a poet, having written numerous works dedicated to her first lover, Thomas Howard (ugh, I ship these two so hard #StarCrossed). Her poems are included along with works of other contemporary poets in a work called The Devonshire Manuscript.