Exploring Alternate Wars of the Roses: Henry Tudor’s Hypothetical Half-Brothers​

By Tyler Parsons


Portrait of Lady Margaret Beaufort

Margaret Beaufort is an extraordinary figure at the heart of the Wars of the Roses. From her earliest infancy, as the heiress to her disgraced father John, Duke of Somerset (d. 1444), her wealth attracted attention. As a child, she was briefly married to John de la Pole, the son of Henry VI’s favourite William de la Pole, Duke of Suffolk.


That match was dissolved after William’s death in 1450, and Margaret moved on to the marriage which would leave her mark in history. In 1455, aged 12, she wed King Henry VI’s half-brother Edmund Tudor, Earl of Richmond. That momentous year, too, saw England plunge into open conflict at the Battle of St Albans. It was at that battle that Margaret’s uncle, Edmund Beaufort, 1st Duke of Somerset, was slain by supporters of his rival Richard, Duke of York.


Further personal losses followed. The following year, Edmund Tudor would die of illness after experiencing a brief imprisonment at the hands of some of York’s adherents in Wales, among them one William Herbert. Margaret was left a pregnant, 13 year old, widow, and gave birth to Henry Tudor in January 1457.


Over the following three decades she would adapt to changing political circumstances in England, persevering through the Yorkist seizure of power in 1461, the brief Lancastrian Readeption in 1470-1, and Edward IV’s second reign thereafter. Throughout, she remained dedicated to the interests of her son, though the pair were often separated- young Henry spending much of the 1460s as the ward of his father’s Welsh rival William Herbert, and being in exile with his uncle Jasper after 1471.


As the Yorkist dynasty unravelled following Richard III’s seizure of power in 1483, Margaret continued to intrigue on her son’s behalf, playing a key role in the rebellion against Richard in October 1483, organising Henry’s crucial betrothal to Elizabeth of York, and ultimately being reunited with him after his victory at Bosworth in August 1485. Thereafter, she would be a central pillar of the early Tudor regime, living just long enough to oversee the accession of her grandson Henry VIII in 1509, as well as becoming a significant font of patronage.


Margaret’s life, however, could be made significantly more complicated. Her extraordinary career included two further marriages after Edmund’s death, to Henry Stafford and Thomas, Lord Stanley. Neither resulted in issue, with there being a general assumption that her youth and small stature at the time of her son’s birth left lingering issues that precluded her from having further children. If we butterfly this, and give Henry Tudor half-brothers, how would that effect the Wars of the Roses, and would it complicate Tudor’s path to the throne and early reign?


Henry Stafford


Margaret married Henry Stafford in early 1458, after the prescribed year of mourning for Edmund had ended. Stafford was the second son of Humphrey Stafford, 1st Duke of Buckingham, and the pair already possessed a familial connection- Henry’s elder brother Humphrey, Earl of Stafford, had married Margaret’s namesake cousin some years previously. That pair produced Henry Stafford, 2nd Duke of Buckingham, whose story would briefly intersect with Margaret’s own in 1483.


The match was also attractive on account of Buckingham being a powerful figure in the early years of the Wars of the Roses. He had spent much of the 1450s as a moderate and advocate of conciliation between York and Margaret’s Beaufort kin. His ultimately loyalty, however, was to the king, and he would die fighting for the Lancastrian cause at the Battle of Northampton in July 1460.


Margaret’s husband would maintain his father’s Lancastrian allegiance, and fought at the Battle of Towton in April 1461, but subsequently made his peace with the Yorkist regime of Edward IV. The couple were not regular features at the Edwardian court, perhaps kept away by Henry’s persistent ill-health or a lack of ambition. Nevertheless, they were on amicable terms with the King- Edward gifted them the manor of Woking in Surrey in 1466, which was afterwards one of their favoured residences.


Many of Stafford’s family, however, played more prominent roles in Edward’s regime. His Bourchier half-uncles were particularly prominent- Thomas, Archbishop of Canterbury, was elevated to Cardinal in the 1470s; Henry was named Earl of Essex and served as Treasurer during Edward’s second reign; and John, Lord Berners, was a Chamberlain to Queen Elizabeth Woodville. His stepfather, Walter Blount, had also been a fixture at the Yorkist court and sometime Treasurer in the 1460s.


Despite her husband’s apparent standoffish approach to politics, Margaret was an active figure during the turbulent years of 1469-1471. During that period Edward IV was betrayed by his cousin Richard Neville, Earl of Warwick, and brother George, Duke of Clarence. In the aftermath of the Battle of Edgecote Field in 1469 William Herbert, the guardian of young Henry Tudor, was executed. The King was brought under the rebels’ power for a brief period, and during this window Margaret and her husband applied to Clarence to receive custody of her son.


Nothing came of this, as Warwick and Clarence’s grip on government proved shortlived, and Edward was swiftly returned to his full royal dignity. Some see the King’s subsequent decision to elevate Henry Stafford’s younger brother, John, to the peerage as Earl of Wiltshire, as a snub directed at Henry Stafford for treating with Clarence.


Nevertheless, Stafford remained loyal to Edward in the years that followed. He helped suppress a rebellion led by his wife’s stepbrother Richard, Lord Welles in March 1470, which resulted in the execution of Welles and his heir. Later that year Edward was briefly deposed by an alliance composed of the traitorous Clarence and Warwick and the exiled Lancastrians. Margaret took advantage of this brief Lancastrian Readeption to reunite with her son, and took the boy to meet with his uncle, the restored Henry VI- a meeting that would assume great significance in later Tudor propaganda.


Stafford was more reluctant to engage with the Lancastrian regime, however, and for good reason. Edward returned to the country in 1471 and swiftly won back his throne. Despite the entreaties of his wife’s cousin, the Lancastrian stalwart Edmund Beaufort, 3rd Duke of Somerset, Stafford ultimately committed to Edward. Having received severe wounds in Edward’s service at the Battle of Barnet in April 1471, he would die in October.


As Edward’s second reign dawned, then, Margaret found herself seeking another husband.


Thomas, Lord Stanley


Quartered arms of Sir Thomas Stanley, 1st Earl of Derby. Image created by wikimedia user 'Geraldiker ' and shared under the CC BY-SA 4.0 licence.

Thomas Stanley was notoriously cautious, and spent much of his career refusing to commit to either side. This served him well, with he and his brother William spending the Wars of the Roses becoming the dominant figures in Chester and Lancaster. Despite refusing to commit in the battles of 1471, Thomas was appointed Steward of the King’s Household by Edward IV after Barnet. Margaret would take him as her fourth husband the following year. She was not yet thirty.


True to form, Thomas maintained his equivocatory position when Richard III seized the throne, and avoided any complicity in his wife’s plots in 1483. He then, famously, declined to join either side in the campaign leading up to Bosworth. It would be William who decisively intervened in that battle, bringing about Richard’s death.


Thomas nevertheless ascended further under the new regime, being named Earl of Derby by his stepson, and accumulated further offices. William would ultimately turn against the King in favour of the pretender Perkin Warbeck, and be executed in 1495, but Thomas would die peacefully in 1504, his self-interested career having survived five decades and five kings.


What would history look like if Margaret had had another son by one of these figures?


First, I think it is important to consider how Margaret’s own behaviour might be effected, particularly in that key period during Richard’s reign. How strong is her bond with distant Henry when she has a younger son to bond with? Does her determination to get Henry back from exile dim a little with the knowledge that any plotting might endanger not only her own life and livelihood, but that of her other child? Could such a child somehow become a hostage to Margaret’s good behaviour, and thus constrain her efforts on Henry’s behalf? Ultimately, I think, given her character, Margaret would still work to reunite her family. In the context of 1483-5, the best way to do that is still to try and bring Henry back as a King.


A Second Son of Margaret Beaufort and the Later Wars of the Roses


In the context of the Wars of the Roses, a son of Margaret and Henry Stafford is the more interesting option because, if born in the first half of their marriage, he’d be a full-fledged adult for those crucial years of 1483-5. We’ll call him ''John'' for the purposes of this scenario.


In early adulthood ''John'' could seek advancement under the tutelage of his Bourchier great-half-uncles- Henry, Earl of Essex, remained Treasurer until 1483, and Cardinal Thomas, Archbishop of Canterbury, lived until 1486. If we constrain the butterflies and assume Margaret still remarries Thomas Stanley, then ''John'' will also have a highly placed stepfather. He might also secure a further in at court via marriage and the acquisition of influential in-laws. Perhaps he manages to find a minor place in the Edwardian establishment in this manner, only to be drawn into the chaos when Richard III’s usurpation and the subsequent rebellion upends this establishment. A more direct route into the chaos might involve ''John'' attaching himself to his volatile cousin Henry Stafford, 2nd Duke of Buckingham. If this was the case, he might share in his cousin’s meteoric rise and equally spectacular fall in 1483. ''John'' might even provide some connective tissue between Buckingham and the rebels organised by his mother, leading the rebellion against Richard in October 1483 to some greater coherence. There are potential difficulties here, though. The vain and egotistical Buckingham might not want to associate with a younger cousin with an arguably superior claim to the throne.


Part of me would be intrigued to see ''John'' betray his cousin, become a Ricardian stalwart, and then stare down his own brother at Bosworth, but that doesn’t seem especially likely. The most minimalist change possible, of course, would involve ''John'' getting involved in the rebellion against Richard, joining in the glut of exiles afterward, and joining up with his half-brother to fight at Bosworth.


The Tudor Rose Combination of the Red Rose of Lancaster and the White Rose of York. Image by Wikimedia user 'Sodacan' and shared under the CC BY-SA 3.0 licence.

By contrast, a son of Margaret and Thomas Stanley will be twelve at most by the time of Bosworth. He’d only really come into his own as a political figure as the 1490s dawned, at the earliest.


A Second Son of Margaret Beaufort and the Early Tudor Regime


The early years of the Tudor regime were incredibly shaky. Henry faced outbreaks of unrest in Northumberland in 1489 and Cornwall in 1497, a rebellion led by Richard III’s nephew John de la Pole, Earl of Lincoln (son of Margaret’s childhood ‘first husband’) and the impostor Lambert Simnel in 1486-87, and multiple incursions by another impostor, Perkin Warbeck, in the 1490s. It was for alleged support of the latter that William Stanley was executed.


An impeccably loyal figure to represent the King’s interests and royal authority could be useful to the Tudor regime in this period, but would Henry’s half-brother fulfil such a description? Margaret will presumably work to maintain harmony between her sons, but there may be points of contention. The younger brother might feel he is not being sufficiently endowed with lands by King Henry, or hopes to marry one of the younger York princesses might be dashed- IOTL Princess Cecily was married to Margaret’s half-brother John, Viscount Welles. Might a younger brother of the King feel himself a more appropriate match? A royal member of the well-established and English Stafford or Stanley families might also be inclined to think themselves more suitable for the throne than the Welsh Henry, whose grandfather Owen could be denigrated as a mere household attendant.


In general, I think Henry’s relationship with a ''John Stafford'' is more likely to be harmonious. The two would have some familiarity with eachother- Margaret and Henry Stafford remained in contact with Henry Tudor throughout the 1460s and had intermittent meetings. If ''John'' crossed the channel and marched alongside his half-brother throughout the Bosworth campaign, that might also encourage some fraternal feeling.


A son of Stanley, on the other hand, will be born after Henry departed into exile and thus the two will be complete strangers. He might also have a chip on his shoulder- not only is he a younger son of Margaret, with all the material uncertainty that implies, but he is also a younger son of Stanley, who had three sons by a prior marriage. If he is denied what he feels to be appropriate grants from his royal brother, in addition to only getting a sliver of the properties of his two very wealthy parents, that could spark discontent. Feeling poorer or less trusted than his non-royal Stanley half-brothers might be a particular grievance.


Perhaps he could drift into the orbit of his similarly discontented uncle, William Stanley, who also felt inadequately rewarded by the Tudor regime, and thus fall into mischief. Given the plethora of difficulties Henry faced IOTL- de la Poles, multiple impostors, Cornish rebels- an extra vector of instability at the centre of his court would be distinctly unhelpful.


Even if things in this period play out mostly as IOTL, the existence of a half-brother of Henry VII would have major repercussions going forward, given the Tudor dynasty’s notorious reproductive difficulties…

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