WI Charles V divides his possessions differently?

Maybe, but still the most sensible option would be give it to the Austrians. I mean, Milan only had strategical value due to the link with the Burgundian lands. Without it, it just becomes a isolated duchy that is a source of conflict with the French. The main Aragonese insterest was in Southern Italy, not the Northern half, and if Milan goes to Austria it might help to strenght the Emperor's power in Italy.
I'm not saying that Spain wouldn't get Milan, but probably the most sensible option would be give it to the Austrians too.

It would probably be the most rational solution, however I do not see the king of Spain giving up both 'Burgundy' and Milan. Holding onto territories by monarchs wasn't always decided on the most rational grounds. Furthermore the reason that the duchy of Milan is a source of conflict with France could just as well be a reason to give it to Spain and not Austria. In the OTL Austria had to face the Ottoman Empire; ITTL they will receive the wealthy Burgundian Circle, however at the price that they will have to pay for a (larger) part the burden of the conflict with France.

Furthermore with Spain controlling the duchy of Milan, they in theory still have a stake in the empire.
 
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Maximilian II was very sympathetic to Protestantism in his youth and continued to show Protestant inclinations even after he reaffirmed his Catholicism. His sympathy was well known, so much so that Ferdinand upon assumption of the Imperial Throne promised Paul IV that he would ensure Maximilian would not succeed him if his son converted.

So then what happens if a sympathetic Maximilian, who by all accounts wanted to convert to Protestantism and would have done so had politics not gotten in the way, is placed as the Monarch of the Protestant Low Countries.

There is an elephant in the room that I'm ignoring in this scenario unfortunately, Maximilian was inclined toward Lutheranism, while the Burgundian Circle to my knowledge was more influenced by Calvin. I have a feeling however likely some form of reconciliation could easily be found, with either Maximilian accepting Calvinism, or some sort of agreement being reached effectively declaring religious tolerance (and by religious tolerance I mean one could be Catholic, Lutheran, or Calvinist, and perhaps Jewish).

The sympathies of Maximilian might very well have been a OTL reason for Charles V, not to give the Burgundy Circle to his daughter and nephew. Obviously Charles V would have wanted that the Burgundian Circle remained Catholic, since he was raised in the Burgundian Netherlands and he was a devout Catholic.
 
Phillip II and the duchy of Milan

Maybe, but still the most sensible option would be give it to the Austrians. I mean, Milan only had strategical value due to the link with the Burgundian lands. Without it, it just becomes a isolated duchy that is a source of conflict with the French. The main Aragonese insterest was in Southern Italy, not the Northern half, and if Milan goes to Austria it might help to strenght the Emperor's power in Italy.
I'm not saying that Spain wouldn't get Milan, but probably the most sensible option would be give it to the Austrians too.

Charles V already made Phillip II duke of Milan in 1540, so in 1548 Charles V couldn't give away the duchy of Milan. OTL this decision disappointed and frustrated some, including Ferdinand, who had ambitions for his own children, and the king of France, who liked the idea that the duchy of Milan should have went to his second son and a Habsburg archduchess upon such a marriage.
Giving the Burgundian Cicle to Mary and Maximilian II upon their marriage (with the provision that if this marriage stayed without children, that the Burgundian Circle was to return to the Spanish Habsburg branch).
Such a deal could have helped to reconcile the differences, one of these differences was the decision made with regard to the duchy of Milan, between Charles V and Ferdinand.
So if the POD is 1548 or at least after 1540, the duchy of Milan is going to stay with the Spanish Habsburgs, because Phillip II already was made the duke of Milan in 1540.
 
Charles V already made Phillip II duke of Milan in 1540, so in 1548 Charles V couldn't give away the duchy of Milan. OTL this decision disappointed and frustrated some, including Ferdinand, who had ambitions for his own children, and the king of France, who liked the idea that the duchy of Milan should have went to his second son and a Habsburg archduchess upon such a marriage.
Giving the Burgundian Cicle to Mary and Maximilian II upon their marriage (with the provision that if this marriage stayed without children, that the Burgundian Circle was to return to the Spanish Habsburg branch).
Such a deal could have helped to reconcile the differences, one of these differences was the decision made with regard to the duchy of Milan, between Charles V and Ferdinand.
So if the POD is 1548 or at least after 1540, the duchy of Milan is going to stay with the Spanish Habsburgs, because Phillip II already was made the duke of Milan in 1540.

Sure, but remember the thread when we discussed at after the Peace of Crepy Charles was arranging to have Ferdinand's daughter married to the Duke of Valois, giving to him as downry the Duchy of Milan? It means that at least he was considering about reverse his decision, and apparently it only didn't happen because the duke died first.
 
Sure, but remember the thread when we discussed at after the Peace of Crepy Charles was arranging to have Ferdinand's daughter married to the Duke of Valois, giving to him as downry the Duchy of Milan? It means that at least he was considering about reverse his decision, and apparently it only didn't happen because the duke died first.

Apparently Charles V did consider taking away the duchy from his 12/13 year old son.
However if a second son of Francis I was to receive the duchy of Milan upon his marriage with a Habsburg archduchess, this son should also have received 4 duchies in appanage from his father according to the treaty.
This treaty wasn't loved by a number of parties: the council of Charles V felt that it was unwise to give up a territory of such a strategic importance, the dauphin didn't like the idea that his brother would receive so many duchies (Milan and 4 appanages), the dauphin felt that his brother was favoured and I wouldn't be surprised if Philip II didn't like it either.

If Charles V would have wanted to give Milan away when Phillip was an adult, Phillip II probably would have made more objections. This probably also applied for the Burgundian Circle, however those possessions were still held by Charles V, in contrast Phillip II was formally the duke of Milan. Furthermore giving the Burgundian Circle and the duchy of Milan to Maximilian II and Mary, and probably also accept Maximilian II as the Habsburg candidate for the next king of the Romans, seems at bit too much. Even with the deals with France it was the Burgundian Circle or the duchy of Milan never both of them.
So the easiest way to make it more agreeable for Phillip II* is to let him keep a territory, which (formally) was already his (in 1548). Besides the duchy of Milan strengthens the position of 'Spain' on the Italian peninsula even further.

(*= Phillip II might have developed ideas on the subject, especially if it meant 'Burgundy' and Milan, similar to the opinion of the dauphin, when Milan and 4 appanages were to go to the brother of the dauphin; so IMHO letting Phillip II keep the duchy of Milan seems sensible.)
 
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Furthermore giving the Burgundian Circle and the duchy of Milan to Maximilian II and Mary, and probably also accept Maximilian II as the Habsburg candidate for the next king of the Romans, seems at bit too much.

I already feared so. In contemporary terms, which multiple of Milano would equal all the Spanish colonies in worth? 0.5? 0.75? ;)
 
I already feared so. In contemporary terms, which multiple of Milano would equal all the Spanish colonies in worth? 0.5? 0.75? ;)

Giving away Spanish colonies (although IIRC they were technically Castillian), probably isn't possible for the same reason that any hypothetical second son of Charles V (in another thread) couldn't receive the 'Spanish' (Aragonese) kingdoms in Italy.

IMHO the only possibility to give all possessions of the house of Habsburg in the empire to the 'Austrian' branch, probably is that they are the senior line.
 
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A way to make the Austrian Branch the senior line of the house of Habsburg is, that Ferdinand of Aragon succeeds in making Ferdinand of Habsburg the heir to the crowns of Castille and Aragon. Under such a scenario Ferdinand of Habsburg would have received 'Spain' and everything else is going to be for Charles V. This will also have implications for the future brides of Ferdinand and Charles V, actually I wouldn't be surprised if Charles V marries Anna of Bohemia and Hungary instead of Ferdinand in OTL.
It could also help if Vladislas II dies childless and that Maximilian, as determined in the treaty of Pressburg (modern day Bratislava), manages to secure the succession to the thrones of Bohemia and Hungary. Another option is that Louis II is never born and there only is Anna, in which case her most likely option for a husband would have been a Habsburg archduke and since ITTL Ferdinand already is going to inherit 'Spain', Charles V would have been the candidate of choice.
Or Louis II dies at a later date, however any negotiation between Maximilian and Ferdinand of Aragon is going to be a lot harder if it is much more uncertain that Charles V is going to inherit a crown.
The Holy Roman Empire was an elective monarchy and although both Bohemia and Hungary were elective at times, it still is much more likely and achievable to (re-)turn Bohemia and Hungary into heriditary monarchies.
 
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