WI/AHC: Alessandro 'il Moro' and Ippolito de Medicis' Roles Were Switched

A recent rereading of the book The Rise and Fall of the House of Medici got me wondering, what if Clement VII De Medici had had a change of heart and dressed Alessandro de Medici in cardinal's skirts instead of his cousin, Ippolito, who becomes duke of Florence, maybe even marries Caterina de Medici, heiress to the duchy of Urbino. What could be the effects of this switch?
 
No interest in Ippolito becoming Duke of Florence (IMHO he was the slightly more competent of the two choices). How might his militant streak change Florentine/Tuscan politics if he doesn't die of malaria (or poison or whatever killed him)?
 
AFAIK (and my knowledge of Italian history at this time is touch-n-go), Cosimo was OFFERED leadership, the famous comment about "some had in mind the glutton, some the innkeeper", because like so many factions offering a theoretical crown they thought Cosimo would be a figurehead who would be beholden to them out of gratitude.
BOTH Alessandro or Ippolito would be IMPOSED on Florence, albeit by a Florentine pope and coming from a Florentine family on a city that threw them out several times. Added to that, a marriage with Caterina is unlikely - she may be legitimate (as opposed to Alessandro or Ippolito) - but besides a tenuous connection to France, she is of no theoretical value, unless Ippolito decides to go reconquering Urbino. In all likelihood, Ippolito marries another Italian noblewoman (Farnese?) or Margarethe of Austria, who can bolster his regime. A possible double French match, Ippolito to Marie de Bourbon (he won't get one of François I's daughters, Henry Fitzroy had a better chance of that) and Caterina to the duc d'Orléans is on the cards, but Clement VII might see that as putting all his eggs in the French basket.

It might be interesting if after the Sack of Rome, when Clement is at least theoretically allied to Karl V, he dusts off Leo X's plan to annex Ferrara and parts of Emilia to the Medici, with imperial support, plus securing a marriage between Ippolito and Margarethe, while at the same time negotiating a marriage for Caterina with a Farnese (Margarethe's OTL husband) or even perhaps, he gets a match to the duke of Orléans for her.
 
AFAIK (and my knowledge of Italian history at this time is touch-n-go), Cosimo was OFFERED leadership, the famous comment about "some had in mind the glutton, some the innkeeper", because like so many factions offering a theoretical crown they thought Cosimo would be a figurehead who would be beholden to them out of gratitude.
BOTH Alessandro or Ippolito would be IMPOSED on Florence, albeit by a Florentine pope and coming from a Florentine family on a city that threw them out several times. Added to that, a marriage with Caterina is unlikely - she may be legitimate (as opposed to Alessandro or Ippolito) - but besides a tenuous connection to France, she is of no theoretical value, unless Ippolito decides to go reconquering Urbino. In all likelihood, Ippolito marries another Italian noblewoman (Farnese?) or Margarethe of Austria, who can bolster his regime. A possible double French match, Ippolito to Marie de Bourbon (he won't get one of François I's daughters, Henry Fitzroy had a better chance of that) and Caterina to the duc d'Orléans is on the cards, but Clement VII might see that as putting all his eggs in the French basket.

Interesting, but might it not lead to the pope being regarded as 'rather a scoundrel' by both the French and the Emperor-King if he sort of stays a middle course between them?

It might be interesting if after the Sack of Rome, when Clement is at least theoretically allied to Karl V, he dusts off Leo X's plan to annex Ferrara and parts of Emilia to the Medici, with imperial support, plus securing a marriage between Ippolito and Margarethe, while at the same time negotiating a marriage for Caterina with a Farnese (Margarethe's OTL husband) or even perhaps, he gets a match to the duke of Orléans for her.

Caterina marrying a Farnese? Would that even be on the cards? I mean, OTL I know she was offered as a bride for James V, Henry Fitzroy (both would've been interesting), but Alessandro Farnese (future Paulus III) is still one of the cardinals, IDK if the Farnese had enough clout for the Medici - though, that said, them getting enough clout can always be a a posteriori thing if the Medici decide to ally with the Farnese and the other Papal families, especially after they've taken half of the d'Este patrimony, plus swiped Urbino from the della Rovere - which I could see calling down France's wrath on them (given that the duchess of Ferrara is the sister to the late queen of France).
Would Karl V be open to Clement annexing the territories in Emilia-Ferrara for the Medici? I mean, that would catapault the Medici into a very important position in Italy, wouldn't it?
 
A wedding between Ippolito and Caterina is likely in the case he will be installed as ruler of Florence. She is the heiress of the main branch of the family and OTL this match was seriously taken in consideration before the Pope named Ippolito cardinal. Sure her title of Urbino was only a title but she was the daughter and only child of the last Medici ruler of Florence and so marrying her reinforced her cousin's power on the city...
 
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A wedding between Ippolito and Caterina is likely in the case he will be installed as ruler of Milan. She is the heiress of the main branch of the family and OTL this match was seriously taken in consideration before the Pope named Ippolito cardinal. Sure her title of Urbino was only a title but she was the daughter and only child of the last Medici ruler of Florence and so marrying her reinforced her cousin's power on the city...

Milian? So the d'Este are not going to be the only ones with a beef with the Medici then? What's left of the Sforza will too, probably?
 
Milian? So the d'Este are not going to be the only ones with a beef with the Medici then? What's left of the Sforza will too, probably?
My mistake. I wrote Milan instead of Florence...
Milan will be still contended between the French (who clkaim the city as theirs) and the Imperial Forces (who will back the Sforzas as rulers)
Alessandro was at least officially an illegittimate son of Caterina's father (likely instead his real father was Pope Clement) so he cannot marry her...
If the Pope decide to make Ippolito the next ruler of Florence Caterina is the most logical choice of bride for him (OTL was talked and both of them were favorable to such wedding)... Her title of Urbino is only a title but she is the last legittimate heir of the family's main branch and daughter of the last Medici ruler of Florence. Married to her Ippolito became the legitimate heir of Caterina's father...
 
Alessandro WAS actually considered as a replacement duke for Milan between the Sack of Rome and Francesco II's marriage. I'll find the link to the article that mentions it. So, Ippolito could ostensibly be considered for the same post?

Here, the link
 
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Alessandro WAS actually considered as a replacement duke for Milan between the Sack of Rome and Francesco II's marriage. I'll find the link to the article that mentions it. So, Ippolito could ostensibly be considered for the same post?

Here, the link

Alessandro/Ippolito could've made an interesting replacement for the reportedly insane Francesco II Sforza. Although, admittedly, a papal bastard being granted Milan (when Milan transitioned from the Visconti to the Sforza, although through a bastard, it was at least someone linked to the former ruling family), would need some link to the legitimacy of the Sforza (which might require him to marry one of Bona Sforza's daughters (and I'm not sure if that is possible).

But then what happens to the Duchy of Florence in this scenario? Does it get joined to the duchy of Milan - sounds a bit like a Medici wank - or does it retain its republican status?
 
Alessandro/Ippolito could've made an interesting replacement for the reportedly insane Francesco II Sforza. Although, admittedly, a papal bastard being granted Milan (when Milan transitioned from the Visconti to the Sforza, although through a bastard, it was at least someone linked to the former ruling family), would need some link to the legitimacy of the Sforza (which might require him to marry one of Bona Sforza's daughters (and I'm not sure if that is possible).

But then what happens to the Duchy of Florence in this scenario? Does it get joined to the duchy of Milan - sounds a bit like a Medici wank - or does it retain its republican status?

Bumping this
 
Something I've been musing on for a Medici Milan was that OTL Alessandro attempted just that when he paid suit to Christine of Denmark, Dowager Duchess of Milan. Could Ippolito try the same stunt? Would it work?
 
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