Pope Wolsey?

References to Thomas Wolsey's attempt to become Pope keep cropping up in my reading. Apparently it was marginally successful though ultimately, of course, he failed. What would be the likely consequences of his success? Would he remember his old patron and grant him the annulment he wanted, or would he become a new-age Thomas Beckett, with much more trouble-making power for his former King?

Apologies if this comes up a lot, I don't frequent Before 1900 very much.
 
Well, let's see. Wosley was made a Cardinal in 1515 by Pope Leo X. He participated in only two elections during his lifetime, which gives us a very narrow window unless we end the life of one of the Popes prematurely.

In 1521, Wosley reportedly received the third most votes, eight out of thirty-nine. Although he received some additional minor support, he fell out of favor quickly when they realized how young he was (48!). In order to win, Wosley needs to make his age a non-issue. Perhaps if there is a sentiment not to have an election in at least a decade, a la JP2, he may have a chance. It would also help to somehow either discredit the other candidates or have one of them throw their support behind Wosley.

The Papal Conclave of 1523 is much easier. Wosley received twenty-two votes, just two votes below the necessary number. Just have him give an inspirational speech or have one of the absent Cardinals attend to draw support to him. Although this scenario is much easier, it gives Wosley less time to make a significant impact on the Church.
 
But Wosley would find the same problems the rest of his contemporaty popes found: England is nicely far,far away in northern Europe, while Emperor Charles has his army right there in Naples.
 
Well for one thing we can be sure is that he would have called himself Adrian as a Pope to honour the only English Pope Adrian IV... As for the election Wolsey had to face Cardinal Medici who wanted St. Peter's Chair badly... Giulio de Medici controlled 1/3 of the conclave and a potential alliance with Cardinal Farnese's party could easily block Wolsey's candidacy but not achieving 2/3 +1 majority. For Wolsey to be elected Pope he would have to lure Farnese to his side and also form an alliance with Cardinal Colonna (was controlling 13 Cardinals) which would have given him sufficient votes for election. For Giulio de Medici since he needed only Colonna's party votes it was simpler but Colonna refused to support him. So the comclave was deadlocked and Medici threw the name of Cardinal Adrian of Utrecht in the table and Colonna supported it. Cardinal Adrian gathered 28 votes (15 from Medici party and 13 from Colonna party) and got elected.
In 1523 conclave Colonna's party had shrunk significally while Medici's party had grew slightly but the key to this conclave were the French and the Imperial Cardinals. The French party was unstable supporting at first Cardinal Fieschi then Cardinal Farnese Farnese and in the end Cardinal Orsini. Wolsey indeed reached 22 votes but his candidacy was quickly dropped when French switched to Cardinal Orsini thus pushing Colonna to direct his 20 Cardinals to vote for Medici (because he didnt want to see his bitter rival Orsini occupying the Throne) thus making Medici Pope Clemens VII...
 
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