Visconti Power Vacuum: What happens if Gian Galeazzo dies without legitimate sons?

Gian Galeazzo Visconti usurped his uncle Bernabo, forged a large duchy in Northern Italy, threatened war with France, and tried to carve himself out a kingdom before dying of fever.

Both the sons from his second marriage died without issue. Milan first passed to the Sforza descendants of his illegitimate granddaughter Bianca Maria. The legitimate issue of Valentina (the daughter of his first marriage who married the Duke of Orleans) would eventually kickstart the Italian Wars over their own claim to Milan.

In toying around with a fun little thought experiment, a different idea stuck with me: what happens if Gian Galeazzo dies without ANY legitimate sons and kickstarts the game of Milanese musical chairs decades early?

Instead of two surviving sons, his second marriage to his cousin gives him two daughters. When Gian Galeazzo dies on schedule in 1402, his kids look like this:

1. Valentina (b. 1371) - Her proxy marriage to Louis of Orleans went through in 1387. The contract stipulated Valentina's issue would inherit if Gian Galeazzo didn't have any legitimate sons. For "reasons of security" Gian didn't actually let Valentina leave until 1389, after the birth of a healthy son. He doesn't get that grace here.

Would Gian still let the match go through? Charles the Mad doesn't have his first breakdown until 1392, but his wife Isabeu of Bavaria (a granddaughter of Bernabo) doesn't have a 'surviving' son until 1392 (by the time that Dauphin dies in 1401, he's got surviving younger brothers). That leaves Louis of Orleans Charles' direct heir.

Does Gian delay the match until he thinks Louis won't inherit the French throne? Or would he love to sew chaos in France (and all those Bavarians in court) by letting it go through on schedule? In either case, Gian has several Orleanist grandsons by his death in 1402.

Or Gian would find a safer husband for Valentina, one better aligned to his immediate interests in Italy without potentially dragging France into the mix?

2. Giovanna Maria (b. 1388) - Instead of the healthy son Gian got IOTL that let the Orleans match go through, he's got another baby girl. Might already be married off by the time her dad dies.

3. Bianca Maria (b. 1392) - Named after Gian's mother, and because I love some cosmic ironies :p Given the state of Italian nobility at the time, could also be married off by 1402, or at the very least betrothed.

Both Giovanna and Bianca have Caterina Visconti as their mother. I can see her pushing for a marriage to one of her Bavarian nephews to unite the competing claims to Milan.

OR maybe to a son of her brother Carlo Visconti, who might have been a catspaw (or just a strategic nuisance) by Bavarian factions against Gian to reclaim Milan for him. Carlo's still just barely alive in 1402, and has two sons around the age of Caterina's daughters: Marco (b. 1383) and Giovanni Carlo (b. ?) Marco died unmarried IOTL, but Giovanni Carlo apparently married and had 2 kids. At least according to one source, he 'usurped' the Lordship of Milan for a month in 1412 and was murdered in Paris in 1418.

OR maybe Gian marries off one of his younger daughters to an Italian captain capable of defending Milanese interests, like Facino Cane? He apparently didn't marry his OTL wife Beatrice until after entering Gian's employ. Maybe Facino or another captain manage to marry one of Gian's daughters in the chaos after his death to get a claim that way?

But we also can't forget about Gian's illegitimate sons.

4. Gabriele Maria (b. 1385) - An illegitimate son, but still a son. IOTL he was apparently legitimated in 1397 (at least according to one source.) He was granted lordships by Gian but later deposed and beheaded by the French governor of Genoa.

Given the lack of any legitimate sons born in his marriage, would Gian favor him even more highly here? Especially since he's a handy loophole out of that son clause in Valentina's marriage. Or would an extremely pissed off Caterina and her relatives manage to foil any efforts to displace her daughters?

5. Antonio (d. after 1414) - Another illegitimate son that, unlike Gabriele, seems to have just... existed.

Or do the Bavarians/Austrians/Luxembourgians/Insert HRE faction here get the grand prize out of this dumpster fire?
 
Bernabo Visconti had a few sons still alive in 1402 and several daughters. Iirc Gian Galeazzo also fathered at least one bastard.

Louis of Orleans would be Gian Galeazzo's choice (or more accurately Valentina and her consort), provided that Louis came and ruled Milan in his own right, rather than as an appange. The marriage contract had stipulated something to that effect. French power was precisely what he was after- his first wife after all was a French Princess-and he would want to ensure a smooth succession, which kept his state intact. It's not inconceivable that Louis takes up with his wife in Milan.

What likely happens is a Mary of Burgundy scenario, with Gian Galeazzo swearing his vassals to his daughter.

More importantly, without a male heir Louis will be much more likely to enter Italy, as Gian Galeazzo vainly hoped he would, and carry out the planned invasion of the Papal States. Louis would hope to rule Romagna as King of Adria, and Valentina would be made his heiress, while the Avignon Pope's were to be forcibly installed in Rome.
 
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