What would happen if Charles and Henry formed an alliance and declared war on France? I'd imagine that England would take most of the territory they had in the days of the Angevin Empire while Charles would seek to link his Spanish territories with the HRE and make his lands more centralized.
 
Pretty sure they did do that and failed, the entire reason why it was so hard for Henry to get an annulment was because Charles was using his influence to make sure it didn't go through.
 
Pretty sure they did do that and failed, the entire reason why it was so hard for Henry to get an annulment was because Charles was using his influence to make sure it didn't go through.
Well before the whole annulment thing, what would happen if Henry and Charles managed to defeat Francis in war and kill him?
 
Then France has it's colonial empire preened and then some reps that inevitably don't get repaid and that's that. Nobody is going to disembowel France at this stage.
 
What would happen if Charles and Henry formed an alliance and declared war on France? I'd imagine that England would take most of the territory they had in the days of the Angevin Empire while Charles would seek to link his Spanish territories with the HRE and make his lands more centralized.
At this point, even in the event of a total and irremediable defeat of France, it was too late for both Charles and Henry to try pulling "My Little Space-Filling Empire".

England more or less switched its priorities from being a continental power to maritime in the latter century after having spent a lot of energy in a basically unwinnable war, and wouldn't be that interested going back to the misnomed "Angevine Empire" (which was more of a feudal hegemony than a direct control).
It doesn't mean in the latest that Henry VIII would be uninterested on having holdouts in France or Brittany : you could expect very well the Pale of Calais being extended, Boulogne being definitely secured, harbours in Brittany occupied, and maybe (in the case of a total victory) most of English Gascony before 1453.
But, in spite of Henry VIII's aspirations (that he gradually gave up), there was no real way to assert mostly symbolical claims to France.

Charles V's ambitions are rather more known and more realistic : the Treaty of Madrid gives a working base there. Basically Charles V would have asked most of the Burgundian estates from Francis I, maybe up to Nevers and Somme's towns (on the latter case, maybe more of an occupation than annexation, but nothing unthinkable); and of course France out of Italy, Navarre and (again, in a maximalist victory, which is not that plausible) maybe Brittany.
In some respects, Philipp II had the same general ambition about France than his father : turning it from a constant pain in the geopolitical ass to a strong enough auxiliary in the region.

Eventually, neither Henry VIII or Charles V had a vested interest crushing France, the first because having a super-powered HRE on steroids wasn't a thrilling geopolitical prospect, the second because he couldn't afford to spent this much ressource (let's remember that, while being deprived of most of the same ressources Charles V had at disposal, Francis I hold his ground relatively well, totally ready to bleed Turkish treasury white if he needed to) and especially while he had to fight French, Protestant, Papal, Ottoman and whatnot at the same time.
While a maximalist victory of England and HRE isn't impossible, and not the most implausible happenance, it would be hard to reach and would more likely end up as a relatively moderated treaty.
 
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What would happen if Charles and Henry formed an alliance and declared war on France? I'd imagine that England would take most of the territory they had in the days of the Angevin Empire while Charles would seek to link his Spanish territories with the HRE and make his lands more centralized.

The alliance happened and the plans had been made. However, when the allies had been as close to achieving their goal as was physically possible, Francis being in Charles' hands after Pavia, and Henry came making noises about his agreed upon share, he was advised by the Spanish to take a hike because he did not play any role in a victory.

Charles ended up with much more modest gains: French king renounced all his claims in Italy, Flanders, and Artois, surrendered Burgundy to Charles, agreed to send two of his sons to be hostages at the Spanish court, and promised to marry Charles' sister Eleanor and to restore to Bourbon the territories that had been seized from him.
 
Well before the whole annulment thing, what would happen if Henry and Charles managed to defeat Francis in war and kill him?

Henry tries his HYW claim? Nah, most likely the victors have a fallout when Henry tries to get into Anne Boleyn's pants. And if he Charles somehow ignored Henry mistreating poor Catherine (or if butterflies make her ill after her hubby won in France/Italy), then the two will have a fallout when Henry splits from the Catholic Church. You know he has trouble siring sons and he keeps blaming the wives.
 
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