This is just an idea I've had bouncing around for a while, it doesn't move too quickly from the OTL for now, mostly since I'm uncertain of Henry's behavior with a surviving possible male heir (i.e. if it will change or stay the same)
1522 – Young Lord Henry Brandon, eldest child of the duke of Suffolk and the former French queen, recovers from a particularly violent but unknown illness. Lord Henry’s cousin, the Princess Mary, only legitimate child (although she has both a bastard half-brother and sister) of the king has recently been betrothed to her twenty-two year old cousin, the most powerful man in the world, Charles, Holy Roman Emperor, King of Spain (which also happens to include all the good bits of Italy the French want and which don’t belong to the Holy Roman Emperor, as well as most of the known world over the Atlantic Ocean), and Duke of Burgundy.
1523 – The French queen gives birth to another son, named Charles, after his father. The former queen of Scots – older sister to the French queen – gives birth to son, Robert Douglas, by her second husband, the Earl of Angus.
1524 – Lady Mary Boleyn gives birth to a daughter that everyone at court is ninety-nine percent sure is the king’s illegitimate daughter. However, unlike with his two older bastards, there is no fanfare, nor even a public acknowledgement. Although, Mary is very hastily married off to Sir William Carey, a gentleman of the king’s privy chamber.
1525 – In June, Queen Katherine’s failure to produce a son is highlighted by the investiture of both the King’s bastard son, Henry FitzRoy, as Duke of Richmond & Somerset, Earl of Nottingham, “with precedence over all nobles save the issue of the king lawfully begotten”, and of Lord Henry Brandon as Earl of Lincoln. It is considered telling by those in the know, as well as later historians, that FitzRoy’s titles of Richmond and Somerset have both been elevated from their previous earldom status, making the boy a “double duke” in a time where, as a modern biographer puts it: ‘the only dukes were the king’s uncle [Norfolk] and the king’s brother-in-law [Suffolk] and now the king’s bastard’.
However, the glimmer of hope extends in the fact that her daughter, Mary, future Holy Roman Empress and Queen of Spain, is sent to the Welsh Marches at Ludlow Castle, where Katherine’s ill-starred marriage to the late Prince Arthur had played out. Mary will serve as the king’s representative on the Welsh Marches, with many of the royal preroragtives that would normally be borne by a legitimate brother.
1526 – The Emperor-King Charles with Henry VIII’s permission, breaks his engagement to the soon-to-be-ten year old Princess Mary, in order to wed the more age-appropriate Infanta Isabel of Portugal. Naturally, Queen Katherine is rather upset at this, since she saw her daughter as the next Empress Matilda – wife of the Holy Roman Emperor, and Queen of England in her own right.
Mary Boleyn, the king’s former dalliance, is delivered of a son. Although legally the boy is the son of Sir William Carey, the whispers at court abound that Mary Boleyn hasn’t barred the king from her bed just because she’s married. Then again, the French king has also referred to her as ‘that great prostitute’.