POD
What will happen if Edward, Prince of Wales died in 1540, followed shortly after by his devastated father? With Henry VIII dead in 1541, Catherine Howard would be the Dowager Queen, a young and rich widow free to remarry, while Mary Tudor will follow his father as Queen. In OTL Mary, after becoming Queen, wanted marry her cousin Charles V, not his son, the future Philip II of Spain, who was 11 years younger than her. In OTL Charles was against remarrying and also feel to old and proposed his already widowed son with advantageous condition for England and gave the Kingdom of Naples to his son for guaranteeing him the status requested by Mary. Here Philip is a 14 years old boy, engaged to Maria Manuela of Portugal, while Charles had lost his beloved Isabella two years earlier and while unwilling to remarry is still capable to generate children (in OTL his youngest illegitimate son don Juan will be born only in 1547). England is a too great prize for losing it or gifting to someone else (and the only other member of the family with the right age and status aka his brother is still married) and Mary is a 25 years old Queen, very conscious of her status and rank who want marry someone who is already a King in his own right.
 
Habsburg of Spain and England
Karl V, Holy Roman Emperor (1500-1560), King of Spain and Duke of Burgundy marry a) Isabella of Portugal (1503-1539) in 1526 b) Mary Tudor, Queen of England (1516-1562) in 1542
  1. a) Felipe II, King of Spain (1527-?) married a) Maria Manuela of Portugal (1527-1545) in 1543 b) Maria of Portugal, Duchess of Viseu (1521-1552) in 1446 c) Christina of Denmark (1521-?) in 1553
    1. a) Carlos II, King of Spain* (1545-?) married Elisabeth of Valois (1545-?) in 1560
      1. miscarriage (1565)
      2. Isabella II, Queen of Spain (1566-?) married Ferdinand VI, King of Spain (1556-?)*
      3. Felipe (1568-1575)
      4. miscarried son (1571)
    2. b) Juan (1548-?), cardinal
    3. b) Alfonso, Duke of Viseu and Aveiro (1550-?) married Juliana de Lencastre, Duchess of Aveiro (1560-?)
    4. b) Leonora Maria (1552-?) married Ernest I of Austria, Holy Roman Emperor (1553-?)
    5. c) Isabella Clara Eugenia (1554-?) married Carlo Emanuele, Duke of Savoy (1555-?)
    6. c) Ferdinand VI, King of Spain (1556-?) married Isabella II, Queen of Spain (1566-?)*
  2. a) Maria (1528-?) married Maximilian II of Austria, Holy Roman Emperor (1527-?) in 1545
  3. a) Ferdinand (1529-1530)
  4. a) stillborn son (1534)
  5. a) Juana (1535-?) married João Manuel, Prince of Portugal (1537-1554) in 1552
  6. a) Juan (1537-1538)
  7. a) miscarried son (1539)
  8. b) Henry IX Philip, King of England (1543-?) married Marie Stuart, Queen of Scotland (1542-?) in 1558
  9. b) Katherine Isabella (1545-?) married Francis II, King of France (1544-?) in 1562
  10. b) stillborn daughter (1548)
  11. b) Charles Edward, Duke of York and Milan (1550-?) married Isabella Beatrice of Austria (1548-?) in 1564

NOTES: ATL Spain will be composed by Castile, Aragon and Portugal as Charles II will inherit Portugal after the death of his cousin Sebastian, the last Avis King of Portugal
 
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Habsburg of Austria
Ferdinand I, Holy Roman Emperor (1503-1564), King of Hungary and Bohemia married Anna of Bohemia and Hungary (1503–1547) in 1521
  1. Elisabeth (1526-1545) married Sigismund II Augustus, King of Poland
  2. Maximilian II, Holy Roman Emperor (1527-?) married Maria of Spain (1528-?) in 1545
    1. Anne of Austria (1549-1569) married Sigismund III, King of Poland in 1565
    2. Ferdinand of Austria (1551-1552)
    3. Rudolf of Austria (1552-1558)
    4. Ernest I, Holy Roman Emperor (1553-?) married Leonora Maria of Spain (1552-)
    5. Elisabeth of Austria (1554-?) married Alexander I, Elector of Saxony (1554-?)
    6. Maria of Austria (1555-1556)
    7. Matthias of Austria (1557-?) married Anne Elisabeth of Austria (1559-?)
    8. stillborn son (1557)
    9. Maximilian of Austria (1558-?), grandmaster of the Teutonic Order
    10. Albert of Austria (1559-?), cardinal
    11. Wenceslaus of Austria (1561-1578)
    12. Frederick of Austria (1562-1563)
    13. Maria of Austria (1564-1564)
    14. Charles of Austria (1565-1566)
    15. Margaret of Austria (1567-?), nun
    16. Eleonore of Austria (1568-1580)
  3. Anna (1528-?) married Albert V, Duke of Bavaria (1528-?) in 1546
  4. Ferdinand II, Archduke of Austria (1529-) married a) Isabella of Poland (1519-1548) in 1544 b) Elizabeth of England (1533-?) in 1550
    1. a) Sigismund III, King of Poland (1545-?) married a) Anne of Austria (1549-1569) in 1565
      1. a) Sigismund (1566-?)
      2. a) stillborn daughter (1567)
      3. miscarriage (1568)
      4. Ferdinand (1569-?)
    2. a) Isabella Beatrice, Duchess of Bari and Rossano (1548-?) married Charles Edward, Duke of York and Milan (1550-?) in 1564
    3. b) Maximilian (1552-?) married Maria Anna of Bavaria (1551-?)
    4. b) Ferdinand (1555-?)
    5. b) Anna Elisabeth (1559-?) married Matthias of Austria (1557-?)
  5. Maria (1531-?) married Wilhelm, Duke of Jülich-Cleves-Berg
  6. Magdalena (1532-?), nun
  7. Catherine (1533-?) married Francesco III, Duke of Mantua
  8. Eleanor (1534-?) married William I, Duke of Mantua
  9. Margaret (1536-?), nun
  10. John (1538-1539)
  11. Barbara (1539-?) married Alfonso II, Duke of Ferrara and Modena
  12. Charles II, Archduke of Austria (1540-?)
  13. Ursula (1541-1543)
  14. Helena (1543-?), nun
  15. Joanna (1547-?) married Francesco I de' Medici, Grand Duke of Tuscany
 
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Avis of Portugal
Manuel I, King of Portugal (1469-1521) married a) Isabella of Aragon and Castile (1470-1498) in 1497 b) Maria of Aragon (1482-1517) in 1500 c) Eleanor of Austria (1498-?) in 1518
  1. a) Miguel da Paz, Prince of Portugal, Asturias and Girona (1498-1500)
  2. b) João III, King of Portugal (1502-1557) married Catalina of Austria (1507-?) in 1525
    1. Afonso, Prince of Portugal (1526-1526)
    2. Maria Manuela (1527-1545) married Felipe II of Spain (1527-?) in 1543
    3. Isabel (1529)
    4. Beatriz (1530)
    5. Manuel, Prince of Portugal (1531-1537)
    6. Filipe, Prince of Portugal (1533-1539)
    7. Dinis (1535-1537)
    8. João Manuel, Prince of Portugal (1537-1554) married Juana of Spain (1535-?) in 1552
      1. Sebastian I, King of Portugal (1554-1568) engaged to Marguerite of Valois (1553-?)
    9. António (1539-1540)
  3. b) Isabella (1503-1539) married Karl V, Holy Roman Emperor (1500-?) in 1526
  4. b) Beatriz (1504-1538) married Charles III, Duke of Savoy (1486-1553) in 1521
    1. Adriano Giovanni Amadeo, Prince of Piedmont (1522-1523)
    2. Ludovico, Prince of Piedmont (1523-1536)
    3. Emanuele Filiberto, Duke of Savoy (1528-?) married Marguerite, Duchess of Berry (1523-?) in 1554
      1. Carlo Emanuele, Prince of Piedmont (1555-) married Isabella Clara Eugenia of Spain (1553-?)
    4. Caterina (1529-1536)
    5. Maria (1530-1531)
    6. Isabella (1532-1533)
    7. Emanuele (1533)
    8. Emanuele (1534)
    9. Giovanni (1537-1538)
  5. b) Luís, Duke of Beja (1506-1555)
  6. b) Fernando, Duke of Guarda (1507-1534) married Guiomar Coutinho (c.1507-1534)
    1. Luísa (1531-1534)
    2. stillborn son (1534)
  7. b) Afonso (1509–1540), Cardinal
  8. b) Henrique (1512-) Cardinal
  9. b) Maria (1513)
  10. b) Duarte, Duke of Guimarães (1515-1540) married Isabella of Braganza (1514-?) in 1535
    1. Maria of Guimarães (1538–1577) married Alessandro Farnese, Duke of Parma and Piacenza (1545-?) in 1565
    2. Catarina of Guimarães (1540–?) married John, 6th Duke of Braganza (1543-?) in 1563
    3. Duarte II, 5th Duke of Guimarães (1541–?)
  11. b) António (1516)
  12. c) Carlos (1520-1521)
  13. c) Maria, Duchess of Viseu (1521-1552) married Philip II, King of Spain (1426-?) in 1546
 
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Tudors
Henry VIII, King of England (1491-1541) married a) Catherine of Aragon (1485–1536) in 15 annulled 1533, b) Anne Boleyn (c.1507–1536) in 1533 c) Jane Seymour (c.1508-1537) in 1536 d) Anne of Cleves (c.1515–1557) in 1540 annulled 1540 e) Catherine Howard (c.1523–?) in 1540
  1. a) stillborn daughter (1510)
  2. a) Henry, Duke of Cornwall (1511-1511)
  3. a) stillborn son (1513)
  4. a) stillborn son (1515)
  5. a) Mary, Queen of England (1516-?), married Karl V, Holy Roman Emperor (1500-?) in 1542
  6. a) miscarried daughter (1518)
  7. b) Elizabeth (1533-?) married Archduke Ferdinand of Austria (1529-?) in 1550
  8. b) miscarried son (1534)
  9. b) miscarried son (1536)
  10. c) Edward, Prince of Wales (1537-1541)
 
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Notes on the scenario
NOTES on this scenario

While Spain's numeration follow that of Castile, I am pretty sure who Ferdinand VI of Spain will be also called Ferdinand III in Aragon and Ferdinand II in Portugal. I ended giving only a surviving daughter to Carlos and Isabella and then marrying her to her half-uncle (under order of Felipe II) was quite natural... Plus another Isabella and Ferdinand on the Spanish throne? I was unable to resist...

I know who maybe I have put too many intermarriages here but really European royals were almost all kins and after inheriting Spain the Habsburg had developed a strong tendency to marry in the family so...

After the death of Sebastian few months before their wedding Marguerite will elope with Henry of Guise while her mother was defining the details of her engagement to the heir of Navarre... The chronicles reported who the King Francis' reaction to the news and the fury of his mother in reporting that was a prolonged laugh and this request: "Mother, please... Now you can stop to intrigue?"... In many suspected who the King had blessed the escape as he was against the Navarrese's match and liked Guise but feared his mother's reaction...
Francis II is born healthier and will live and reign many years and have children by Katherine, his sister Claude will be married to the Duke of Lorraine as OTL. Henry II died as OTL during the tournament for the wedding of Elisabeth to the Prince of Asturias but Catherine de'Medici here will never be in power as regent and instead will be remembered as the feared French "Queen of Intrigues" and for being the cause of her children's embarrasses and exasperation (King Francis II most cited quote was "You know my mother, there is little who I can do..."). In the end Francis exiled her in her lands of Auvergne and Boulogne in 1573...

I have not thought too much to the children for both Francis II of France and Henry IX of England but I know who Henry IX' eldest son will be Charles II James, King of England, Scotland, Ireland and Duke of Burgundy and Lord of the Netherlands and he will be a good friend of his cousin Charles IX of France.
Christine of Lorraine will be the only surviving daughter and heiress of Charles III and Claude of France, but I am uncertain about her wedding… she will likely end as Queen of England or France (or Lorraine, marrying Henry IX’s second son)…

As was asked why Sigismund of Austria and not Johan Vasa as king of Poland after Sigismund II:
Isabella of Poland died when her son was three and the boy was under Elizabeth’s supervision (who was a great supporter of her stepson as heir of Poland, as that would have made her sons as heirs of their father) starting from four years. Sigismund II here never married Catherine of Austria because Barbara Radzwill lived but they remained childless. When Sigismund was around ten year old, his stepmother sent him to his uncle in Poland as ward and the Sejm pretty much accepted him as heir (in OTL they were pretty desperate to have an heir from Sisgimund). Johan is only married to a Jagiellon princess while Sigismund is son and grandson of two Jagiellon princesses and was partially raised in Poland and his wedding to Archduchess Anne was arranged between Sigismund II and Maximilian II. So I do not think who Johan will have great chances against someone who is practically a Polish prince with just the wrong surname...
 
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Do the English kings now hold any land within the Holy Roman Empire?
Yes, as ATL the whole Burgundian inheritance will go to Henry IX, while his younger brother will be given Milan (and is married to a cousin with Sforza blood)
 
Yes, as ATL the whole Burgundian inheritance will go to Henry IX, while his younger brother will be given Milan (and is married to a cousin with Sforza blood)
I ask because this to me looks like some messy, super corrupt imperial elections are i the future of this timeline. I had caught the part about Milan.
 
I ask because this to me looks like some messy, super corrupt imperial elections are i the future of this timeline. I had caught the part about Milan.
Not really, as the English Kings will care very little about imperial elections, as they do not have much interests in that part of the world
 
on the last phase of Italian wars
Another interesting thing is who the Italian wars will be highly influenced by this butterflies, at least since the 1542-1546 campaign. Sure in OTL Henry VIII was allied with Austria, but Charles having direct control over England and his armies is a different thing, so maybe Francis will think thrice before starting that war? Also the conclusion will be different as now Charles has already a son who is heir to Burgundy and Netherlands and can hope in another to put as heir of Milan so he will not be so interested in playing the young Charles d’Orleans against his elder brother Dauphin Henry, if that mean depriving his own sons from part of their inheritance
 
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so maybe Francis will think thrice before starting that war?
I have developed my anti-habsburg, pro-france dream team! Viva la France! So it consists of France, Portugal? (maybe the join because they are intimidated by the Habsburgs), the Ottomans, the Scandinavian states (if they can stop fighting one another, Russia (when that becomes an option), Irish and German states (disloyal to England and the Habsburgs) and Poland-Lithuania (if it can be convinced to join). I know it is unlikely but I could see a few of these countries coming together, especially France and the Ottomans,
 
I have developed my anti-habsburg, pro-france dream team! Viva la France! So it consists of France, Portugal? (maybe the join because they are intimidated by the Habsburgs), the Ottomans, the Scandinavian states (if they can stop fighting one another, Russia (when that becomes an option), Irish and German states (disloyal to England and the Habsburgs) and Poland-Lithuania (if it can be convinced to join). I know it is unlikely but I could see a few of these countries coming together, especially France and the Ottomans,
Portugal will NEVER join an anti-Habsburg alliance, Poland-Lithuania would NEVER ally with the Ottomans (and were willing enough to work with the Habsburg), most of the German states and Poland-Lithuania would not join an alliance in which the Ottomans are involved, Scandinavian states are not so interested in join such alliance (as Denmark and Sweden have their fights). Resign yourself to the idea who here France is screwed as circled by three of the five branches of the Habsburg
 
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