The Tudor Duke of Milan

Henry Fitzroy, DUke of Richmond and Somerset, bastard son of Henry VIII, was proposed at some point as a candidate for the Imperial vicariate as duke of Milan (at least that is my understanding of it). At another point in time, he was offered as a husband for an Austrian archduchess (or at least half-Austrian, since he was considered for both Maria of Viseu and Dorothea/Christine of Denmark). Now what if these two events coincide. But instead of marrying a legitimate princess, Karl V marries his bastard daughter, Margarethe, to Henry (now Duke Enrico I)?
 
There is a big difference between being offered by Henry VIII and accepted by Charles V. While a marriage between two royal bastards would be equal and thus more likely to be accepted giving Fitzroy Milan would be a real stretch considering that in OTL it went to Emperor Charles V's son Philip II of Spain. Maybe you could have the Hapsburg's propose him as a neutral alternative as an effort to avoid the Italian War of 1535 but it's fairly unlikely. Charles V hated Francis I of France and was happy to go to war with him, he didn't want to compromise.
 
My main reason for thinking this is that Alessandro de Medici (Margarethe's OTL first hsband) raised his candidacy for filling the vacant position of duke of Milan after Francesco Sforza died, so the possibility exists of Karl V naming a duke that isn't his son - however, the French aggression following Sforza's death meant that Karl felt his underage son (under his regency) would be a better candidate.
 
My main reason for thinking this is that Alessandro de Medici (Margarethe's OTL first hsband) raised his candidacy for filling the vacant position of duke of Milan after Francesco Sforza died, so the possibility exists of Karl V naming a duke that isn't his son - however, the French aggression following Sforza's death meant that Karl felt his underage son (under his regency) would be a better candidate.

I haven't heard that Alessandro de Medici had a crack at Milan but considering he had his hands full with Milan I doubt it got very far. It's a nice idea but I can't see a chain of events that would end with Fitzroy in Milan.
 
Top