Yet Another Tudor Line of Succession Question

Hi! I'm working on a book and I wanted some opinions for my alternative history.

So, in this timeline Anne Boleyn and Henry VIII have the following children:
Princess Elizabeth b. 1533
Prince Henry, Prince of Wales b. 1536 d. 1546
Prince Edward b. 1537
Princess Blanche b. 1538

Anne dies after giving birth to Princess Margaret.

Henry then remarried to Jane Seymour, his pregnant mistress.

Princess Jane/Joan b. 1539
All of Henry's other marriages go as per OTL.

Back to the Boleyns. The Boleyn siblings living in this timeline are as follows:
Mary Boleyn b. 1499
George Boleyn b. 1504
Thomas Boleyn b. 1506
Anne Boleyn b. 1507

What I planned to do is, Catherine of Aragon still dies on schedule. Anne gives Henry his son not too long after and Henry takes this as a sign from God that yes, his marriage to Catherine was unlawful in the eyes of God and Anne Boleyn returns to high favor. In this triumph and with a second son born shortly after there's still the Mary problem. Mary has even less leverage to stand on with Henry in this situation. My idea is that Mary is wed to Anne's brother Thomas to bring her to heel and get her to finally accept all of her father's demands.

Thomas is set with a Dukedom and Mary is wed to him and they have three children with two girls that end up having children:

Lady Catherine Boleyn b. 1539
Lady Elizabeth Boleyn b. 1542
Thomas Boleyn b. 1545 d. 1554

My question is, when Henry VIII writes his will do you think he's adding Mary back to the line of the succession? If so, is he adding her before or after her sisters? Feel free for any other speculation and comments but I've got a large part of the story nailed down, I just want to hammer down some of the finer details.
 
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If Henry comes to see his marriage to Catherine of Aragon as unlawful, I can't imagine him putting Mary in the line of succession straight after her brothers. Legally, he should, but I doubt he would.
 
If Henry comes to see his marriage to Catherine of Aragon as unlawful, I can't imagine him putting Mary in the line of succession straight after her brothers. Legally, he should, but I doubt he would.
That's what I'm thinking as well but I was also looking at it maybe from a line of temperament. Maybe with two healthy sons and feeling less paranoid and stressed because of it along with Mary possibly being more amenable that it may get her restored to the succession, but Henry is still Henry. That being said, how will the people of England see it?
 
Henry would have ZERO reason for marrying Jane Seymour here and if Henry has two legitimate sons and only one annulled wedding and one Act of Succession Mary would NEVER be restored to the line of succession (and she marrying Anne’s brother is both unlikely and useless)
 
Henry would have ZERO reason for marrying Jane Seymour here and if Henry has two legitimate sons and only one annulled wedding and one Act of Succession Mary would NEVER be restored to the line of succession (and she marrying Anne’s brother is both unlikely and useless)
Well in the novel's narrative it's kind of a quickie thing because Jane so happens to be pregnant around the time Anne is dead so it's just more an opportunity of convenience. He doesn't want to miss the chance of having a third son. But I am curious, what do you think Henry will do with his eldest daughter in this scenario? Does he just leave her out to dry? There are no convents to send her off to.
 
Well in the novel's narrative it's kind of a quickie thing because Jane so happens to be pregnant around the time Anne is dead so it's just more an opportunity of convenience. He doesn't want to miss the chance of having a third son. But I am curious, what do you think Henry will do with his eldest daughter in this scenario? Does he just leave her out to dry? There are no convents to send her off to.
My favourite method of dealing with Mary in situations like this is marrying her off to Gregory Cromwell.

He's only four years younger than her, his father would remain a loyal supporter of Anne if she has a son, and, as a future Baron, he has the rank and wealth that make him a suitable match for the King's acknowledged daughter.
 
My favourite method of dealing with Mary in situations like this is marrying her off to Gregory Cromwell.

He's only four years younger than her, his father would remain a loyal supporter of Anne if she has a son, and, as a future Baron, he has the rank and wealth that make him a suitable match for the King's acknowledged daughter.
Oooo I didn't even consider Cromwell. Though, Anne and Cromwell would probably still butt heads over the monastery funds, right? Then again, if Anne could push for the match it would probably smooth out their issues I thinking.
 
Oooo I didn't even consider Cromwell. Though, Anne and Cromwell would probably still butt heads over the monastery funds, right? Then again, if Anne could push for the match it would probably smooth out their issues I thinking.
Cromwell's no fool. If Anne has a son, he knows he won't be able to do a thing against her.
 
Oooo I didn't even consider Cromwell. Though, Anne and Cromwell would probably still butt heads over the monastery funds, right? Then again, if Anne could push for the match it would probably smooth out their issues I thinking.
They would, but I doubt a canny political operative like Cromwell would be stupid enough to move against the woman who has given Henry his heart's desire. He might not approve of what Anne wants to do with the monasteries, but he's not going to be open about it, not when Anne is the unchallenged Queen of Henry's heart.
 
Cromwell's no fool. If Anne has a son, he knows he won't be able to do a thing against her.

They would, but I doubt a canny political operative like Cromwell would be stupid enough to move against the woman who has given Henry his heart's desire. He might not approve of what Anne wants to do with the monasteries, but he's not going to be open about it, not when Anne is the unchallenged Queen of Henry's heart.
This I can agree with, Cromwell is very smart. Though looking from Anne's perspective, do you think she'd still be wary or suspicious of Cromwell after this clash? Because I can see it going the reward/pull you back into the Boleyn faction route or her maybe begin pushing him out and trying to pull more favor towards the Boleyns. But yes I agree Cromwell would probably try to kiss and make up after the birth of a son.
 
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