WI: Anne Boleyn has a son in 1534, who then dies at the age of 14?

Not really. The Emperor had a lot of trouble and rember who Henry was still an anointed King and Mary his subject... The Emperor had too many enemies at that time for fighting also England over the question of Anne, Mary and Catherine and if he (like OTL already shortly before Anne's fall) need the alliance of England against France (and still more important need who England do not ally with France against him) and Henry had a male son by Anne, you can be sure who Karl V can be persuaded to recognize the validity of Henry and Anne marriage, recognize Anne as legitimate Queen of England and her son as Prince of Wales in exchange of an alliance and the support of English ship and soldiers against France

I was actually talking about the (admittedly remote) chances of Henry beheading Mary if she doesn't accept being made illegitimate, but fair enough.

Oh, and I forgot, Catherine of Aragon is still alive when *Edward was born, how do you think she'll react?
 
Well, Catherine will probably consider the boy no more than a bastard, unfortunately. She was a stubborn woman (and in a poll they did once of which of Henry VIII's wives you'd go out for drinks with, the order was 1) Anne Boleyn; 2) Catherine Howard; 3) Jane Seymour (although you'd have to put up with her brother tagging along); 4) Anne of Cleves; 5) Catherine of Aragon; 6) Catherine Parr), for instance, if you refused to address her by her title of Queen of England, she would refuse to talk to you.

She'll probably have to work ten times harder for her letters to the emperor or the pope to gain traction on Henry, since the fact of the matter is, Anne giving Henry a son confirms Henry's argument that his first marriage was "cursed" because he'd taken his brother's wife, plus it makes Catherine out for a liar (whether she is or not) in regards to her protests that the marriage hadn't been consummated.
 
If Henry has a living male heir and Mary do not accept what King Henry think is his place and her own, at the best poor Mary will end in the tower for the rest of her (likely short, considering the place, the situation and her always bad health) life and at the worst she will directly lose her life. Catherine is born as Spanish princess, so had protection from that but Mary was english by birth, daughter and subject of Henry so Spain had not any right to interfere in anything Henry decide to do at her...
Catherine of Aragon was a Spanish-born princess and an anointed Queen (but many other princesses and anointed Queens were in her same situation with less luck than her).
Mary Stuart's execution by Elizabeth was an outrage because Mary was not a subject of Elizabeth. She was a Scottish born (so foreign) princess, an anointed and ruling Queen of another nation so Elizabeth had not really right to kill her but Henry with Mary? He had all the right if he think that was needed
 
Princess Elizabeth would almost certainly be betrothed come 1547, and abroad no doubt. Anne Boleyn knew that to counter-act Mary's Spanish blood and Imperial ties she needed a prestigious foreign match for her child(ren) abroad - she had the political savvy to know she needed to do the same thing Henry VII had done after acquiring the throne: underline his own supreme and unquestioned royalty by marrying his children into the old, rich, prestigious dynasties on the mainland.

The Francophile Queen Anne would have pushed her son towards a French princess - though Charles V might have wavered enough in the years that followed to offer the Archduchess Eleanor or Margaret or Barbara to England too. We might even see a reconciliation with Rome once Catherine of Aragon was dead. Elizabeth would be in similar consideration for both pro-France and pro-Spanish matches, as Henry VIII flitted back and forth trying to wiggle his way into shoulder-to-shoulder line-up of Charles V and Francis Ier.
 
Henry VIII of England (b.1491: d.1547) m. Catherine of Aragon (b.1485: d.1536) (a), Anne Boleyn (b.1501: d.1564) (b)

1a) Stillborn Girl (c.1510)

2a) Henry Tudor, Duke of Cornwall (b.1511: d.1511)

3a) Henry Tudor, Duke of Cornwall (b.1513: d.1513)

4a) Henry Tudor, Duke of Cornwall (b.1515: d.1515)

5a) Mary Tudor (b.1516: d.1540)

6a) Stillborn Girl (c.1518)

7b) Princess Elizabeth Tudor (b.1533) m. Charles de Valois, Duke of Orleans (b.1522: d.1557) (a)

1a) Miscarriage (c.1550)

2a) Stillborn Son (c.1551)

3a) Henry de Valois, Duke of Cornwall (b.1552: d.1552)

4a) Edward VII of England (b.1554)

5a) Stillborn Girl (c.1555)

6a) Anne de Valois (b.1556: d.1557)​

8b) Edward VI of England (b.1534) b. Cecilia of Sweden (b.1540)

9b) Miscarriage (c.1536)

10b) Princess Margaret Tudor (b.1538) m. John III of Sweden (b.1537: d.1592) (a)

1a) John IV of Sweden (b.1559)

2a) Anne Cecilia Vasa of Sweden (b.1561)

3a) Henry Vasa of Sweden, Duke of Finland (b.1562)

4a) Miscarriage (c.1564)

5a) Isabella Vasa of Sweden (b.1569)

6a) Stillborn Son (c.1571)

7a) Miscarriage (c.1573)​

11b) Stillborn Boy (c.1540)

12b) Henry Tudor, Duke of York (b.1541: d.1541)​
 
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