WI: Margaret Douglas marries Francis III, duke of Brittany and Dauphin

I think Margaret Douglas can be the replacement bride of Mary Tudor in the betrothal of Francis III of Brittany and Mary Tudor because Mary Tudor is third in line, this would mean a possible French-Scottish war for England if Mary and Elizabeth die without issue.
 
I think Margaret Douglas can be the replacement bride of Mary Tudor in the betrothal of Francis III of Brittany and Mary Tudor because Mary Tudor is third in line, this would mean a possible French-Scottish war for England if Mary and Elizabeth die without issue.

Mary was NEVER third in line. And Margaret held a rather amorphous position at the English court - although in one of the Succession Acts she was inserted AHEAD of her Stewart half-siblings IIRC. So, while Marge might be seen as a fitting match for the likes of Alessandro de Medici, the Dauphin might be a different story. Most of the French saw the duc d'Orléans' marriage as a waste (François I, included), so for François to give away TWO sons to quasi-royal brides might be a bit of a stretch.

Besides, the duc de Bretagne died in August 1536, any pro-French policy at the English court had previously been centred on a match between the Princess Elizabeth and the duc d'Angoulême; and from Easter 1536 (if not January) England had been drifting into the imperial camp once more. Scotland's king isn't going to foot the bill for his half-sister's dowry because 1) he hated his stepdad so it wouldn't surprise me if he's transferred that dislike to his halfsister; 2) he wants his own French marriage (promised by the Treaty of Rouen) and Scotland's not important enough that she merits TWO French royal marriages; and 3) Marge was in Jolly Old England at that point IIRC, which means she'll marry where her uncle says, rather than her half-brother.
 
What about Antoine of Bourbon marrying Catherine of Medici and Margaret Douglas marrying Henry II of France..

Why? Clement wanted a tie to France (the reason for the marriage) and France wanted the lands Caterina stood to inherit from her childless aunt. Margaret, OTOH, is neither a princess nor an heiress, so if Caterina came to François stark naked as he said after Clement died, then Margaret would be still worse than that.
 
Why? Clement wanted a tie to France (the reason for the marriage) and France wanted the lands Caterina stood to inherit from her childless aunt. Margaret, OTOH, is neither a princess nor an heiress, so if Caterina came to François stark naked as he said after Clement died, then Margaret would be still worse than that.
Antoine's parents were denied of the inheritance of Bourbon due to Constable Bourbon's actions, I think marrying Catherine to Antoine might mean that the Bourbons can claim their original inheritance confiscated from them..

I think Margaret can marry the Duke of Orleans in this scenario.
 
Antoine's parents were denied of the inheritance of Bourbon due to Constable Bourbon's actions, I think marrying Catherine to Antoine might mean that the Bourbons can claim their original inheritance confiscated from them..

I think Margaret can marry the Duke of Orleans in this scenario.

Uh why would Caterina bring ANY Bourbon lands back to Antoine? De la Tour lands in Auvergne and Boulogne, sure. The Bourbon-Vendômes lost their title of duke of Bourbon first to Louise of Savoy, Css d'Angoulême, and when she died, her grandson got them. Then when he died in 1545, the title of duc de Bourbon went vacant. I'm not sure if it was restored to Antoine or the Bourbons per se before the ascension of Henri IV.

Either way, Caterina's uncle wants an alliance between François and the Medici, not the Medici and some random French prince who a) isn't very high in the French succession (4e/5e at the time, and most would've laughed at you had you said his son would be king of France); b) not very wealthy (most of the 'good stuff' went to Louise of Savoy; and c) not even in possession of his inheritance (the actual dukedom of Bourbon etc as well as the Alençon lands which ended up in Marguerite d'Angoulême's hands despite her being a childless widow of the last duke, whose main heirs would've been his sisters, the duchesse de Vendôme (Antoine's mom) and the marquise de Monferrat. The marriage between Antoine and Jeanne was a sop to the Bourbons that, in a roundabout way, they were getting the lands that should've been theirs to start with).
 
Uh why would Caterina bring ANY Bourbon lands back to Antoine? De la Tour lands in Auvergne and Boulogne, sure. The Bourbon-Vendômes lost their title of duke of Bourbon first to Louise of Savoy, Css d'Angoulême, and when she died, her grandson got them. Then when he died in 1545, the title of duc de Bourbon went vacant. I'm not sure if it was restored to Antoine or the Bourbons per se before the ascension of Henri IV.

Either way, Caterina's uncle wants an alliance between François and the Medici, not the Medici and some random French prince who a) isn't very high in the French succession (4e/5e at the time, and most would've laughed at you had you said his son would be king of France); b) not very wealthy (most of the 'good stuff' went to Louise of Savoy; and c) not even in possession of his inheritance (the actual dukedom of Bourbon etc as well as the Alençon lands which ended up in Marguerite d'Angoulême's hands despite her being a childless widow of the last duke, whose main heirs would've been his sisters, the duchesse de Vendôme (Antoine's mom) and the marquise de Monferrat. The marriage between Antoine and Jeanne was a sop to the Bourbons that, in a roundabout way, they were getting the lands that should've been theirs to start with).

What about giving Catherine a chance to rule her own lands?
 
What about giving Catherine a chance to rule her own lands?

Might work. Unfortunately, as Queen Adelaide said to Victoria's remark of "wanting to be my own mistress": "you will dream of freedom, but you shall not get it. Every husband will come with strings attached"
 
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