WI: Anne St. Leger Is Born Male

[Kellan Sullivan]

In case you don't know who the lady in the title is, she was the niece of Edward IV and Richard III and cousin of Elizabeth of York.

She was also the personification of some of the shady legal dealings that Edward pulled off in his reign. Her mom, Anne of York, was Edward's eldest sister. Anne (of York) had been married to the Lancastrian duke of Exeter since the age of 8yo. The duke of Exeter was descended from John of Gaunt's second daughter, Elizabeth, and by all accounts, not a nice character. Still, needs must and he and Anne had one child, a daughter, named Anne (yeah it might have just been easier if they'd just named them no. 1, no. 2, etc), who later married Thomas Grey, marquess of Dorset (son of Elizabeth Wydeville), but died without children.

Anne (of York) finally decided enough was enough and petitioned for an annulment of her marriage. She'd already taken up (apparently) with Thomas St. Leger. The annulment came through, and Anne (of York) and Thomas (St. Leger) got married. They had a daughter, Anne St. Leger. And then Anne (of York) died and this was where the shady legal dealings came in.

When Anne (Holland), only child of the now conveniently-accidentally-dead-looked-like-murdered duke of Exeter, had died, Edward IV had made it that her mother (his sister, Anne of York) was her beneficiary with the idea that Anne (of York) could pass all of this on to any other child she had. Of course, Queen Elizabeth Wydeville was all ears, and when little Anne (St. Leger) became the heiress, the queen wanted a second stab at trying to get her hands on the Holland fortune for her grandson (Thomas Grey's eldest son), and arranging the marriage of the two children.

Of course, things didn't happen that way. Richard III had other plans for Anne St. Leger apparently (ICR where he wished to marry her, but he was very conscious of her position as an heiress). And then Henry VII married her off to Baron de Ros and her descendants later became the earls and then dukes of Rutland. IIRC, it was through DNA from her descendants that the identity of the remains of Richard III were confirmed when they were discovered.

But what if she'd been born male? Does Edward (seems as likely a name as any, but mostly it's confusing with all the Thomases running around) St. Leger get the dukedom of Exeter? Or does he simply get the wealth to go with it but not the title itself? In Richard III's reign, would he be a more likely candidate for "heir" than the earl of Lincoln? How would he react to Richard losing at Bosworth? Flight to the continent (Burgundy, perhaps?) or would he wind up in an all-expenses paid vacation in the Tower? And if he's in the Tower, will he be able to ride out the storm and emerge alive? Or will he be like his cousins, Warwick, (possibly) Warbeck, and several de la Pole boys, and be made a head shorter?

 

[Tyler96]

But what if she'd been born male? Does Edward (seems as likely a name as any, but mostly it's confusing with all the Thomases running around) St. Leger get the dukedom of Exeter? Or does he simply get the wealth to go with it but not the title itself? In Richard III's reign, would he be a more likely candidate for "heir" than the earl of Lincoln? How would he react to Richard losing at Bosworth? Flight to the continent (Burgundy, perhaps?) or would he wind up in an all-expenses paid vacation in the Tower? And if he's in the Tower, will he be able to ride out the storm and emerge alive? Or will he be like his cousins, Warwick, (possibly) Warbeck, and several de la Pole boys, and be made a head shorter?

Regarding the prospect of being Richard's heir, IOTL Thomas St Leger was executed for being involved in the 1483 rebellion against Richard, assuming that still happens it'd be awkward trying to make Edward St Leger heir. In any case, I don't see Richard considering it- he's not a full grown adult who can act as an able lieutenant, like Lincoln (making Lincoln heir might also have had the ancillary purpose of trying to get active support from his father the Duke of Suffolk), and if you're going to make a kid heir you might as well go with Warwick (unless you believe those rumours about Warwick being simple-minded, which I don't)- the actual male-line heir, and the only legitimate male Plantagenet other than Richard himself (I know there was stuff about Warwick's claim being extinguished by Clarence's attainder, but that seems legally iffy).

Much would probably depend on where Edward St Leger is at the time of Bosworth, and whose custody he is in (and whether that person is proactive enough to spirit him off to the continent). It must be noted that Edward himself is only ~9 at the time of Bosworth, so what happens to him is entirely dependent on the adults around him. If his father still gets executed I imagine he becomes a royal ward? And the question is then where Richard sends him.

If he stays in England under the Tudors much depends on his personality, how inclined he is towards plotting, to what extent he can buddy up to the Tudors etc. Given the historical track record of those with royal blood under the Tudors he'll want to tread very, very, carefully.

He does have a couple surviving uncles, who will likely be very interested in the life and career of their royal-blooded nephew. I don't know anything about them, but if they're feeling ambitious they might drag their nephew into trouble with plotting and what not.

The fact that he had a relatively humble father might help him fly under the radar a little bit, but OTOH if he's got all the Holland lands he might be a powerful figure that the Tudors want to keep an eye on. He'll probably be treated less harshly than Warwick though- Warwick's mere existence as the last true male Plantagenet undermined Tudor legitimacy.

Regarding the inheritance, is it possible that after the Yorkists are deposed the actual heirs come out of the woodwork and try and get the land back? Would Henry VII be amenable to such a suit? The closest blood relative to Henry Holland 3rd Duke of Exeter appears to Ralph Neville 3rd Earl of Westmoreland, who was the son of Henry's only sister Anne Holland, would he be the rightful owner of the lands? If so, the Tudors might not want to over-aggrandise him by letting him have all the Holland land.

Regarding Ed St Leger having a career as a Yorkist pretender- there are a lot of variables. There are plenty of other claimants, and impostors could still rise up. In the short term, if Ed does turn up in Burgundy, it's probably easier for anti-Tudor forces to use him than what happened IOTL (the whole thing with Lambert Simnel claiming to be the Earl of Warwick, despite the fact that Henry VII had the actual Earl of Warwick in his custody). Later on, it depends if Ed St Leger is seen by disaffected Yorkists as a better bet than someone like Warbeck or the de la Poles, and whether he's on board with any plotting.

Of course, even if he avoids being used as a Yorkist pretender/pawn in his youth he could still end up getting into trouble- maybe the Tudors deprive him of his legally dubious inheritance and he plots against them on that basis, maybe he keeps questionable company and is close to Buckingham or the de la Poles and goes down with them, maybe he is utterly blameless and completely loyal to the Tudor regime but loses his head anyway because of paranoia surrounding his royal blood.

 

[Kellan Sullivan]

Anne (of York)'s husband, also had a bastard son, Robert de Holand, who had two daughters (and who seems to have fought for Tudor at Bosworth - whether because he was a die-hard Lancastrian or whether he supported Lizzie of York IDK), but whom I can't find any thing on him beyond the fact that his wife was named Margaret, and he had two daughters

If the 3e duke of Exeter's inheritance is denied to Westmoreland, next in line would be Anne (de Holand)'s husband, James Douglas, a Scotsman who is also earl of Douglas, but the Tudors might just do as OTL and not recreate the dukedom, at the risk of the duke being an overmighty subject (a second Kingmaker Neville maybe), a foreign earl with no kids or a bastard (Robert de Holland). The legal iffiness of St. Leger's inheritance would probably mean that the dukedom isn't recreated, while his inheritance is left intact - but they might still recreate it at a later point if St. Leger proves his loyalty (although they only recreated it as a marquessate for the earl of Devon so who knows)

 

[Tyler96]

The legal iffiness of St. Leger's inheritance would probably mean that the dukedom isn't recreated, while his inheritance is left intact - but they might still recreate it at a later point if St. Leger proves his loyalty (although they only recreated it as a marquessate for the earl of Devon so who knows)

Conversely, I suppose if Ed St Leger does get in trouble he can be attainted and the crown can seize the Holland inheritance, to do with it as they wish.

 

[mcdnab]

The Exeter inheritance was settled by Act of Parliament in January 1483 - all bar a small settlement which went to the Queen's younger son would go to Anne and her future husband Dorset's heir - her father was stripped of his household posts by Richard III and Anne's custody and wardship appears to have gone to Buckingham, who with Dorset out of the picture might have been plotting a marriage of his own heir.
St Leger's death and Buckingham's fall meant that Anne was stripped of the inheritance by Parliament in 1484 - so she went from heiress to just a well connected young woman.

Exeter would under normal circumstances have lost his estates to the crown - so technically as with the Warwick estate the King decided to provide for relatives without the benefit of a proper attainder.

Richard III's reversal of the act meant the crown benefited a decade after it should have done - clearly the King wasn't that bothered about his niece - incidentally Richard didn't grant the estates to Ralph Neville either.

Had Anne been a boy - then he would have been hampered a bit - his parents marriage was clearly odd given St Leger was a mere gentleman and the annulment of her first (we don't know the grounds used) marriage would be perhaps attacked as Edward IV's marriage was - in strict terms by a pro-Richard person - the St Leger boy would have been heir presumptive (discounting Edward IV's issue as illegitimate, George of Clarence's as barred by his attainder) but I doubt he would have figured much.

 

[Kellan Sullivan]

Interesting @mcdnab. So Edward St. Leger would be in a possibly even worse position than Anne was OTL? He's well-connected but of a lower marriage with his mom's annulment (the annulment's finalization dates to when Exeter would've been imprisoned in the Tower following the Readeption, which means Anne could've sued on grounds of "abandonment")

 

[Kellan Sullivan]

Can I just ask something about OTL's Anne St. Leger? Which of Dorset's sons (the eldest, Edward, or the second, Thomas) was she betrothed to? Because, in addition to struggling to find dates for Edward (or a marriage date, since his wife, Anne Jermingham was supposedly maid of honour to Mary Tudor in France,"which was where she and Grey married. But according to one source (actually the only source I can find with a birthyear mentioned for Anne), Anne Jermingham was born in 1484 - which would've made her 30yo by the time Mary goes to France! And rather old for a first time bride. Sir Edward is equally silent on birth and death dates. All I know about him is that he predeceased his dad.

It makes little sense to my mind, at least, for Anne St. Leger to marry Dorset's son and heir (who's already getting Cecily Bonville's money/estates). However, for Anne to marry a second son (who's getting a smaller share, if at all) and he perhaps be recreated duke of Exeter somehow does. I'm not sure if said husband WILL be created duke of Exeter in the event of an Edwardian Yorkist survival, but his (the second son) marriage to an heiress seems like it would arouse less resentment at court about the grasping Wydevilles than Cecily Bonville's son and heir.

 

[Kellan Sullivan]

A follow-up question about OTL Anne St. Leger, in a Yorkist survival scenario, say she marries Edward/Thomas Grey (whichever was the second boy). Would he be created "1e duke of Exeter" of a new creation? Or would Anne hold the dukedom in her own right, with her son succeeding her as 2e duke?

 

[isabella]

A follow-up question about OTL Anne St. Leger, in a Yorkist survival scenario, say she marries Edward/Thomas Grey (whichever was the second boy). Would he be created "1e duke of Exeter" of a new creation? Or would Anne hold the dukedom in her own right, with her son succeeding her as 2e duke?

Likely Anne would be the Duchess in her own right but at the same time her Grey husband would be Duke “jure uxoris” as that was the most common situation at that time

 

[Kellan Sullivan]

Likely Anne would be the Duchess in her own right but at the same time her Grey husband would be Duke “jure uxoris” as that was the most common situation at that time

Any ideas what lesser titles were/would be attached to it? If it's Dorset's firstborn he would get Marquess of Dorset, Baron Ferrers of Groby. But AIUI noble estates in England weren't in the habit of partitioning stuff unless circumstance abc required it.
The only title I could maybe see a second born Grey boy inheriting are a title that is apparently marked with a question mark (Baron Astley - in theory belonging to the senior male in his descent from Baroness Astley (Elizabeth Wydeville's grandmother-in-law)) and Baron Harrington (Cecily Bonville's title but which none of her kids seemingly inherited).

 

[mcdnab]

The titles are as follows Baron Astley (debated whether it passed from Joan to her descendants or not - none of the Grey's used it - if it was extant then would have been forfeited in 1554), Baron Ferrers of Groby (inherited by the 1st Marquess of Dorset on his grandmother's death), Baron Harrington and Baron Bonville - held by all the Marquesses of Dorset.
Dorset, Ferrers of Groby, Harrington and Bonville all were forfeited on the execution of Henry Grey. Had he not been executed the Dukedom of Suffolk would have been extinct - Dorset would have passed to his younger brother's and their male line descendants (who later become Baron's Grey of Groby and then Earls of Stamford) - the Baronies of Ferrers of Groby, Bonville and Harrington would have gone into abeyance between the three Grey daughter's (if they died without issue then the abeyance would have terminated in favour of their uncle)

 

[mcdnab]

Likely Anne would be the Duchess in her own right but at the same time her Grey husband would be Duke “jure uxoris” as that was the most common situation at that time

Extremely unlikely in my view likely Exeter would have been a new creation for dorsets heir. She had no legal claim on the title unlike the countess of Warwick for example

 

[isabella]

Extremely unlikely in my view likely Exeter would have been a new creation for dorsets heir. She had no legal claim on the title unlike the countess of Warwick for example

Well, Anne would be the second Duchess after her mother...

 

[Kellan Sullivan]

Extremely unlikely in my view likely Exeter would have been a new creation for dorsets heir. She had no legal claim on the title unlike the countess of Warwick for example

So we'd have Edward Grey, 1e duke of Exeter, rather than Anne, 3e duchess of Exeter? Would the subsidiary titles be included in his creation? If so, what? Earl St. Leger, maybe?
P.S. I like the idea of him getting the barony of Astley (by mere dint of it not being held by the Dorset line OTL), maybe it getting bumped up to a viscountcy or an earldom at some point.

Well, Anne would be the second Duchess after her mother...

I imagine Edward V would want to distance himself from the dodgy deals of his dad regarding inheritance (Richard III reduced her to merely Lady Anne St. Leger IIRC), and would create his half-nephew "duke of Exeter" Its hardly as though they were going for continuity here. Anne de Holland was duchess. Then her mother (a York/Plantagenet) succeeded her, only to be succeeded by her younger daughter (St. Leger). Next duke will be Grey. He is not claiming it in rght of his de Holland descent, nor is his wife - so I could see that Edward V/Parliament would want a sort of legal figleaf to cover it.

 

[mcdnab]

Firstly on the death of the 3rd Duke of Exeter his title became extinct. Anne de Holland was never Duchess of Exeter in her own right (and she died before her father and mother)
Commonly at this period widow's tended to use their highest rank even if they remarried - the Queen's mother was usually styled Duchess of Bedford (even after her remarriage) as did the Duchess of Norfolk - so Anne of York was usually styled Duchess of Exeter rather than Lady St Leger - even though she had actually divorced Exeter and remarried before his death - again she was never Duchess of Exeter in her own right.
The Exeter annulment was based on their relationship consanguinity - Exeter argued with only four witnesses the papal dispensation covered it - however unsurprisingly Anne had far more witnesses and the Church ruled in her favour.
The Holland estates had been settled on Exeter's former wife in 1461 at the same point the couple separated and Exeter was attainted a remainder to their daughter Lady Anne Holland was made in 1467 - on the death of Lady Anne 1st wife of the Marquess of Dorset - the estates were dealt with by Parliamentary Act and settled on Anne St Leger (after the death of her mother) and Richard Grey - Edward's stepson.
Now assuming Anne St Leger married Dorset's heir as was planned - it is possible that the Exeter inheritance added to to Dorset's own family inheritance would mean a future King Edward V might raise his half-nephew to Ducal rank and the obvious would be to create him Duke of Exeter of a new creation.
In due course he would of course become 2nd Marquess of Dorset etc - so there wouldn't be any real need for further subsidiary titles (it wasn't a requirement as heirs of peers were often simply the Lord ... etc at this period) - the future Grey Duke's of Exeter would be in addition Marquess of Dorset and Baron Ferrers of Groby, Harrington and Bonville.
The dukedom was extinct so no fig leaf was really needed - titles went extinct from time to time and were sometimes recreated for a distant connection (the Earldom of Essex for the Devereaux family who were descended from the Bourchier Earls of Essex for example) but often were simply handed out because they were free.

 

[mcdnab]

Assuming that Anne Duchess of Exeter dies giving birth to Edward St Leger instead of Anne - then there is far less incentive for Edward to settle the entire inheritance on to the boy (in OTL - it gave Edward's stepson power and wealth and made up for the death of his first wife Anne Holland) - Edward may instead divide it in a different way - a proportion to Anne's widower Sir Thomas (a loyal member of Edward's household who had already received some generous grants dating back to the 60s) with some for his son, some for the King's younger stepson Richard Grey and perhaps the rest to the Crown.

Technically Exeter would have been attainted and his lands forfeit anyway - though Edward's actions in the 1470s certainly penalised the Holland co-heirs who in normal circumstances should have inherited them - principally the 3rd Duke's sister Anne Countess of Douglas and her son Ralph Neville (later 3rd Earl of Westmorland though his father had also been attainted).

Under Richard III the lands were not granted to Ralph - though he did gain some properties from Richard and the reversion of the Countess of Richmond's lands.
The lands eventually ended up with the Stanley's (from Richard III and confirmed by Henry VII) but the vast bulk went to the King's mother Margaret Beaufort in 1485 she also gained some of the Holland Earls of Kent's lands as well.