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Exploring Alternate Wars of the Roses: King Holland

By Tyler Parsons

Arms of Henry Holland

Henry Holland, Duke of Exeter, has much in common with his brother-in-law George, Duke of Clarence. Like Clarence, Exeter was a volatile royal duke with an impressive pedigree who simply… never amounted to much. Like Clarence, it didn’t have to be this way…

Exeter: A Life

The Exeter title derived from Henry Holland’s grandfather, John. John was a half-brother of King Richard II, and did well out of Richard’s reign. In the 1380s he was created Earl of Huntingdon and married the King’s cousin, Elizabeth of Lancaster. The promotion to the Duchy of Exeter came in 1397, after he had assisted in Richard’s removal of his enemies, the Lords Appellant- an action which infamously included the murder of the King’s uncle Thomas, Duke of Gloucester.

In 1399 Richard was deposed by his cousin, and John’s brother-in-law, Henry IV. John did not profit from his connection to the new King, being stripped of his ducal title and ultimately executed in early 1400 after plotting to restore Richard to the throne. His son, also named John, loyally served Henry V and Henry VI in France, earning back Huntingdon in 1416 after his valorous conduct at the Battle of Agincourt, and Exeter towards the end of his life in 1444.

Henry Holland succeeded his father in 1447, aged 17. Late in his father’s life he had been married to Richard, Duke of York’s daughter Anne, though she was still a child (born in 1439). Despite his ducal title Exeter remained relatively impoverished, the family having never been great landowners. Exeter’s father had bolstered his financial standing by successive marriages to wealthy widows, the benefits of which would not pass to his son, and Henry faced further problems with the loss of territories granted to his father in France and a stepmother who enjoyed her dower lands until her death in 1457.

Aggressive attempts to expand his patrimony and improve his financial standing saw Exeter acquire a reputation for violence and brutal conduct. The family seems to have had a tendency towards recklessness, with the first Duke having infamously murdered Ralph Stafford in 1385. His grandson would enter into a feud with Ralph, Lord Cromwell, seizing Cromwell’s manor of Ampthill, Bedfordshire in 1452 with an armed party. Resentment at the wealth enjoyed by Cromwell, as well as the fact that the property had previously been held by his step-grandfather, may have further motivated Exeter. As justification for his actions, he had concocted a fraudulent claim and began directing spurious accusations of treason at Cromwell.

The following year the realm was plunged into uncertainty with King Henry VI’s descent into catatonia. One might expect Exeter to benefit from his father-in-law York being named Lord Protector in March 1454, but the relationship between the two was not amicable. In May Exeter attempted to incite a rebellion, being joined by Thomas Percy, Lord Egremont- who was himself engaged in a deadly feud with York’s Neville supporters. The Nevilles, for their part, had allied with Cromwell in 1453, when Richard, Earl of Salisbury’s son Thomas wed Cromwell’s niece and co-heir Maud Stanhope.

Exeter reportedly laid claim to the Duchy of Lancaster, attempted to ally with the Scots, and claimed the government. The first two seem likely to be exaggerations made by his enemies, with the crux of the matter being Exeter’s challenge to York’s status as Lord Protector, an office he felt entitled to as a closer relation to the King than his father-in-law.

In any case, the rebellion was a failure, and Exeter was imprisoned in Pontefract Castle for the remainder of York’s Protectorate. He was released in March 1455 after the King’s recovery, only to be re-incarcerated after York’s victory at St Albans in June. In the meantime, Ampthill was recovered by Lord Cromwell, though his subsequent death meant Exeter escaped potentially ruinous litigation.

In the uneasy period of truce between 1455 and 1459 Exeter further aligned with York’s enemies, feeling his authority as hereditary Lord Admiral being impugned by the piratical activities of York’s ally Richard Neville, Earl of Warwick. Despite this alignment, and his status as the King’s second-cousin, Exeter was never in the Lancastrian inner circle, being briefly detained in Queen Margaret’s Berkhamsted Castle after he had imprisoned a lawyer in the Tower for reasons known only to himself.

Nevertheless, when hostilities resumed Exeter sided firmly with the King, and served in most of the major battles of the 1459-1461 period. This included Wakefield in December 1460, which resulted in the death of his father-in-law York and brother-in-law Edmund, Earl of Rutland, as well as Salisbury and his son Thomas. The final confrontation of this period, however, would prove to be a resounding Lancastrian defeat. At Towton, in March 1461, Exeter’s brother-in-law Edward secured the throne for the House of York. Exeter lost two bastard brothers in the battle and its aftermath, though he himself escaped. Subsequently, he fought at an assault on Carlisle Castle in mid-1461 and with Jasper Tudor, Earl of Pembroke, at Twt Hill in October. Thereafter he went into exile, first in Scotland and then, by 1463, on the continent.

In his absence the entirety of his estates were vested in his wife Anne of York by her brother Edward IV. The couple’s only child, Anne Holland (born somewhere between 1455 and 1461), was married to Edward’s stepson Thomas Grey in 1466, though she had died without producing issue by 1474.

Exeter would eventually return to England in 1471, after Warwick had betrayed Edward IV and restored Henry VI to the throne. The restoration was fleeting, however, with Warwick defeated and killed at Barnet in April, and the remaining Lancastrians defeated at Tewkesbury in May. The latter battle saw the death of the Lancastrian heir Edward of Westminster, and its aftermath saw Henry VI quietly disposed of in the Tower.

Illustration of the Battle of Barnet (14 April 1471) on the Ghent manuscript

Exeter himself was grievously wounded at Barnet, and ultimately committed to the Tower. During his imprisonment there his wife secured a divorce, and carried Exeter’s lands into her new marriage to Thomas St Leger. He would only see the outside of the Tower in 1475, after he had ‘’volunteered’’ to join Edward IV’s expedition to France. On the return journey he ‘’accidentally’’ fell overboard and drowned, with the King a likely culprit. Drowning at the instigation of Edward IV, of course, provides another point of comparison with Clarence and his malmsey wine.

The purported motive of Edward IV is that after the death of Henry VI and his only son in 1471 Exeter- as the senior legitimate, English-born, descendant of John of Gaunt- could arguably claim to be the Lancastrian heir to the throne.

He was not the sole potential Lancastrian claimant- Clarence himself had supposedly been recognised as next-in-line after Edward of Westminster during his lukewarm participation in Henry VI’s restoration, and John of Gaunt’s senior legitimate heir was Afonso V of Portugal- but he was certainly a credible one.

Could anything have come of this claim?

Exeter: A King?

If he had been spirited away after Barnet, or even managed to slip away during the French expedition in 1475, Exeter could easily still be eking out an existence in exile come the great crisis of the House of York in 1483.

Legally, he’s a more convincing candidate than Henry Tudor- Tudor’s claim derived from the Beauforts, an illegitimate line previously barred from the throne, whilst Exeter’s descent is unimpeachably legitimate. Of course, the idea that a claim to the throne can pass through the female line does tacitly acknowledge that the House of Lancaster were usurpers to start with and the House of York are the rightful rulers, but that little fact didn’t stop Tudor IOTL.

There are other considerations, however, that might prove an impediment.

If he’s feeling brazen Tudor might refuse to fall in behind Exeter as the Lancastrian claimant, trying to use his status as Henry VI’s nephew to boost his own claim. Such division within the exiled Lancastrians would be a major hindrance to any attempt to regain England.

Even if that situation is avoided, there’s the fact that Exeter isn’t an especially appealing candidate for Kingship. He has a known propensity for violence and brutality, and has never enjoyed much success in battle over his long career. Additionally, his long exile makes it doubtful he could rally much support in England on his own merits- Tudor at least had his Welsh heritage and his uncle’s popularity there to leverage for support.

The most severe problem, by far, is that Exeter is a man in his fifties with no legitimate children. Fighting to restore him to the throne only to have him die without an obvious heir or, at best, a young child from a hasty marriage after securing the throne, would be an unappealing prospect.

Theoretically, Exeter’s heir is his nephew Ralph Neville, 3rd Earl of Westmoreland (from 1484), but Westmoreland is something of a nonentity, causing no trouble for Richard III or Henry VII IOTL. A nephew to whom he is a complete stranger is hardly a promising heir on which Exeter could rest any attempt to claim the throne.

Perhaps you could concoct some scenario where Exeter and Tudor can come to some agreement, whereby Exeter names Tudor his heir in default of any children, but such an uneasy arrangement isn’t a great foundation on which to build an alliance. Even if they were successful things could still fall apart- with the fate and marital prospects of Elizabeth of York likely a major point of tension. Exeter could try to marry her himself, but marriage to an elderly brute likely to die without producing issue would be an unappealing prospect to Elizabeth and her Woodville relations. Tudor would similarly be opposed to such a match for fear it will produce issue and displace him in the succession. By contrast, if Tudor endeavours to marry Elizabeth, Exeter may fear this is a prelude to being deposed.

A more interesting possibility would arise if Exeter were to possess legitimate descendants. There are two possibilities here, which I will discuss in turn. The first scenario is his daughter Anne surviving to produce issue with her husband Thomas Grey. The second is providing Exeter with a son, either in place of, or in addition to, Anne.

As a quick note, this analysis will proceed on the assumption that the Rebellion against Richard III in October 1483 goes reasonably historically. The precise dynamics are likely to be different with a surviving Exeter as a plausible Lancastrian claimant, but a foiled rising that results in many Edwardian loyalists getting forced into exile still seems likely. A more in-depth look at this Rebellion and its AH potentialities will be the focus of a future article in this series.

Edward IV meets his wife-to-be, Elizabeth Woodville as painted by James William Edmund Doyle

Anne Holland and Thomas Grey

Thomas Grey, Marquess of Dorset, was the eldest son of Edward IV’s Queen, Elizabeth Woodville. Richard III’s seizure of power in 1483 resulted in the execution of his uncle Anthony Woodville, Earl Rivers, and full brother Sir Richard Grey; the withdrawal of his mother and half-sisters into sanctuary; and the disappearance of his two young half-brothers into the Tower. Dorset subsequently joined the rebellion against Richard in October and fled to the continent in the wake of its failure.

Historically, he joined Henry Tudor in exile, but his support was lukewarm. Indeed, he attempted to defect back to Richard III at his mother’s behest, after she had made her peace with the King. He was intercepted without getting very far, and on account of his doubtful loyalties was left behind in France as surety for a debt when Tudor sailed for England in August 1485. Nevertheless, he was restored to his estates after Tudor’s victory at Bosworth, with his descendants further entangling with royalty and his great-granddaughter Jane being exalted to the throne for a vanishingly brief period in 1553.

In our scenario, Anne Holland has survived and the couple have a few young sons by 1483. When Dorset flees to the continent there is no need for him to defer to Tudor, because his father-in-law possesses the more plausible Lancastrian claim. Their relationship may be tense- Dorset has spent several years enjoying Exeter’s hereditary estates, and Exeter may share the widespread view of the Woodvilles as parvenus- but some sort of working partnership can be struck up if they both accept it’s their best chance for returning to England.

So, Exeter styles himself as Lancastrian heir to the throne, the succession is assured by the existence of his Grey grandsons, and Dorset brings with him connections to the disaffected Edwardian Yorkists. Is such a partnership better or worse off than Tudor was IOTL?

Exeter’s claim is theoretically superior to Tudor’s, but when you’re at this level of remoteness such legal niceties don’t matter a great deal. Exeter’s reputation for violence might make him less appealing than Tudor, who had been in exile since his teens and was essentially a blank slate to potential supporters in England, but that reputation may have faded over two decades of exile (especially given the attrition suffered by the English nobility over the period). Tudor had other advantages, however- his stalwart uncle Jasper at his side, a formidable mother working on his behalf in England, and the Stanley step-father and step-uncle who played such a crucial role at Bosworth. Exeter’s closest ally is a son-in-law he barely knows, and he possesses no real close ties within England.

Finally, and perhaps most crucially, Tudor was able to pledge to marry Elizabeth of York as a sweetener to win the support of Yorkists alienated by Richard III. Supporting Tudor was thus a way for Edward IV’s daughter to become Queen, and for his grandson to become King. In our scenario, supporting Exeter and Dorset is a way to get… a stepson of Edward IV as the son of a King, and eventually a great-nephew of Edward as King. That is a fair bit more tenuous. Dorset was also far from universally popularly amongst the Edwardian establishment- his rivalry with Edward’s staunch friend William, Lord Hastings, helped make Richard III’s coup possible.

Evenifthe Edwardian Yorkists can bring themselves to back Exeter and Dorset- placing the desire to see their exile ended and properties restored over any vestigial loyalty to Edward IV’s memory- and they subsequently manage to depose Richard III, the claim of an unmarried Elizabeth of York would be a cause of major tensions in early in the reign of King Exeter. Unfortunately, the most obvious way to resolve the issue, marrying Elizabeth to Exeter’s eldest grandson to unite the Lancastrian and Yorkist claims, seems unpalatable- both because nephew/aunt marriages are distasteful (and not just to modern sensibilities, as demonstrated by the public opprobrium at the rumours Elizabeth would marry her uncle IOTL) and because of the likely age difference.

Young Exeter

The alternative is that Exeter and Anne of York have a son. Such a child is presumably raised in Yorkist England, it being unlikely Exeter could find the time or opportunity to abscond with the boy whilst fleeing into exile. The child would then inherit the Holland estates upon his mother’s death in 1476 in his mid- to late-teens, and possibly be recreated Duke of Exeter by his uncle Edward IV.

Such a child provides a potential peaceful route to the throne for the House of Holland. If he stays loyal to his uncle he could take John de la Pole’s place as Richard III’s favoured nephew, and be named heir after the death of Richard’s own son Edward of Middleham. Alternately, Young Exeter could, like Dorset, find his way to the continent after involvement in the Rebellion against Richard in October 1483- Anne of York’s second husband, Thomas St Leger, was executed for his participation historically, so it seems likely Young Exeter could be drawn in.

There he could make common cause with his estranged father, with the elder Exeter providing some credibility with the long exiled Lancastrians and the younger being a familiar face to the disaffected Yorkists. An adult son and heir puts Exeter’s potential kingship on a firmer footing, and if Young Exeter is reasonably personable he might counteract his father’s rougher edges. If unmarried- not unreasonable given Young Exeter is in his early 20s- he could also take up Tudor’s OTL pledge to marry Elizabeth of York, thus securing the support of the Edwardian Yorkists and uniting the Yorkist and Lancastrian claims. For this reason I’d judge it a better chance of success than the Exeter/Dorset alliance.

Young Exeter might also have built up a reasonable affinity during Edward IV’s reign, giving him his own support base and personal ties of loyalty to draw on, something not always available to those who been in exile for a prolonged to period. The core of the Holland patrimony was in the Southwestern England, whilst Henry had tried with limited success to establish himself in Bedfordshire and Northamptonshire.

The minutiae of an alternate campaign is beyond the scope of this post, but it seems likely that a Holland-centric attempt to unseat Richard- in either of the permutations we’ve discussed- would focus on the West Country rather than taking the Tudors’ route through Wales. Such a strategy would place the likely confrontation further from Richard’s northern power base, which might adversely affect the number and reliability of the troops he can summon. Many prominent exiles from Richard’s regime also had influence in the area- IOTL Giles Daubeney and John Cheyne were both ennobled by Tudor for their support, whilst Edward Courtenay was restored to the attainted Earldom of Devon- which can be allied to whatever forces Dorset or Young Exeter can rouse.

On the other hand, it doesn’t seem likely that there’s comparable depth of feeling for the Hollands in the West Country as there was for the Tudors in Wales. Additionally, Richard III had deputised his good friend Francis, Viscount Lovell, to guard southwest England when bracing for an invasion in early 1485. As a stalwart supporter of Richard, Lovell seems likely to provide vigorous resistance to a hostile landing. This stands in contrast to the men Richard had entrusted with the defence of Wales, Rhys ap Thomas and Walter Herbert, who readily defected to the Tudors IOTL.

Regardless of whether the alternate geography of such a campaign is advantageous or disadvantageous for Richard, ultimately everything would, of course, come down to the luck of battle…



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