Henry VII: The Master Strategist Who Outsmarted Europe's Powerhouses
How a cautious king navigated treacherous political waters to secure his throne and elevate England's status
What happens when a king, driven by shrewd calculation and unwavering resolve, finds himself surrounded by Europe's most powerful rulers, each with their own agenda to either coerce or court him? In 1496, Henry VII was facing a web of complex alliances, opportunistic rivals, and persistent threats to his crown. But he was not to be underestimated. Henry deftly maneuvered through Europe's turbulent political landscape and not only secured his throne but elevated England's standing on the continental stage. He did this by signing two often overlooked but monumental treaties: The Holy League, or League of Venice, and Intercurses Magnus.
The European Chessboard
In 1496, Europe was a fragmented tapestry of kingdoms, duchies, and evolving states, each realm driven by its own quest for dominance and prestige. In the eye of this political hurricane were several key players:
France, under King Charles VIII, was aggressively expanding its territory, notably through a brutal invasion of the Italian peninsula aimed at claiming the Kingdom of Naples. Charles had pacified his royal rivals in the years prior before turning his full attention to this conquest.
Spain's Catholic Monarchs, Ferdinand II of Aragon and Isabella I of Castile, sought to curb French ambitions and extend their own influence across Europe. A few years prior, In 1492, they had finally overpowered the last muslim stronghold and conquered the Nasrid Kingdom of Granada. Following this success they helped bankroll a certain Genovese explorer set on finding a new trade route to the Indies. (We all know what Columbus ended up finding instead).
The Holy Roman Empire, led by Maximilian I, held personal resentment towards Charles VIII and French expansion. Frustratingly for Henry VII, the de facto Holy Roman Emperor had also championed Perkin Warbeck and was, not so subtly, backing the imposter's efforts to unseat Henry VII.
The Papacy, with Pope Alexander VI ( Rodrigo Borgia) at its helm, feared the encroachment of French forces into the Italian peninsula and sought allies to defend the Papal States.
Amidst these powerful entities stood Henry VII of England, a relatively new king focused on stabilizing his realm after years of civil war. Despite the fact that England was not considered as significant in sophistication or authority, Henry's strategic importance was undeniable. His alliances and enmities could tip the balance of power in Europe—a fact not lost on his contemporaries. As much as they probably hated to admit it, they needed Henry. The King of England, however, was not a man to be bullied into submission.
The Persistent Threat of Perkin Warbeck
Complicating Henry's position to keep his kingdom at peace was the enduring threat posed by Perkin Warbeck. Warbeck was the pretender claiming to be Richard of York, youngest of the Princes in the Tower and a legitimate heir to the English throne. Warbeck's claims were bolstered by significant backing:
Margaret of Burgundy, sister to Edward IV and Richard III, fervently supported her supposed “nephew” Warbeck, providing him with resources and legitimacy. Margaret proved to be an unbudging rival to Henry’s position. Duke Philip the Fair of Burgundy, Maximilian’s son, looked the other way from his step grandmother’s continued machinations in the years prior to 1496.
Maximilian I, the Holy Roman Emperor and step-son to Margaret, also extended support to Warbeck, seeing an opportunity to destabilize England and possibly place a pliable ruler on its throne. There’s also the possibility that the childless Warbeck named Maximilian his successor should he die without an heir.
Even with Henry reactively shutting down each threat, Warbeck continued flitting between Europes’s kingdoms and rallied support from each opportunistic ruler. Whether he showed it or not Warbeck posed a genuine threat to Henry's reign, forcing the king to remain vigilant and cautious in his foreign and domestic policies.
Balancing Acts: France, Peace, and Profit
Despite the pressures, Henry had managed to maintain a profitable peace treaty with France known as the Treaty of Étaples. Signed in 1492, this agreement sent Warbeck packing after receiving initial support from the Charles VIII. It also provided England with a substantial annual pension from France in exchange for peace and the end of English support for Brittany’s independence. Charles was able to move in on the vulnerable Duchy of Brittany, marry it’s young heiress, Anne of Brittany, and absorb into France.
This peace was lucrative and strategically beneficial for Henry:
It halted French support for Warbeck, reducing immediate threats to his throne.
It filled English coffers, strengthening the economy and Henry's ability to govern effectively.
It kept England out of costly military conflicts, allowing Henry to focus on internal stability.
However, the formation of the Holy League in 1495, an alliance aimed at countering French aggression in Italy, put Henry in a delicate position. Joining the league could threaten his profitable peace with France, but remaining outside could isolate England and diminish its influence.
Joining the Holy League: Caution Meets Opportunity
Isabella I of Castile and Ferdinand II of Aragon were eager to solidify England's participation in the league. They exerted pressure on Maximilian I to withdraw support for Warbeck. However, Maximilian's stubbornness and continued covert support for the pretender complicated matters. In this letter from Maximilian I’s ambassador to the leaders of the Republic of Venice on February 19, 1496 shows just how unyielding Maximilian was in regard to the matter:
“The King of the Romans made answer, that he had recently received letters from the Duke of York (Perkin Warbeck) informing him that his affairs were prospering, and that, through the disturbances imminent in England, he hoped for victory. That it would indeed be unfortunate—as the Duke had embarked in the undertaking at his (the King of the Romans') persuasion, and placed hope in him—if, through the negotiation for bringing Henry VII. into the League, the Duke of York's success should be impeded; by so much the more as, were the Duke of York to obtain the crown, the King of the Romans and the League might avail themselves of England against the King of France as if the island were their own.”
You kind of have to love that level of audacity.
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Throughout the negotiations Maximilian I remained a thorn in Henry's side. The English king initially hesitated entering the league, leveraging his indecision to extract assurances from other members of the league. He already had a union in the works with the Spanish monarchs, The Treaty of Medina Del Campo, which sought to marry their youngest Spanish Princess, Catherine of Aragon to Henry VII’s heir Arthur Tudor. This would bring the kingdoms into a prosperous trade and military alliance. By having this agreement ongoing Henry effectively isolated the Holy Roman Emperor, reducing his capacity to interfere in English affairs.
In the end Maximilian buckled. Henry officially joined the League of Venice on July 18th, 1496 much to the joy and celebration of everyone in the confederacy: Ludovico Sforza Duke of Milan, Republic of Venice, Pope Alexander VI, Isabella I and Ferdinand II, Maximilian, Holy Roman Emperor. The King of England wisely ensured that his involvement was nominal, refraining from direct military action against France to preserve the benefits of the Treaty of Étaples. Although he was pressured to attack France from Maximilian he stood his ground only agreeing to do as much as the other rulers as stipulated in the treaty.
Henry officially joined the League of Venice on July 18th, 1496 much to the joy and celebration of everyone in the confederacy: Ludovico Sforza Duke of Milan, Republic of Venice, Pope Alexander VI, Isabella I and Ferdinand II, Maximilian, Holy Roman Emperor. The King of England wisely ensured that his involvement was nominal, refraining from direct military action against France to preserve the benefits of the Treaty of Étaples.
The Intercursus Magnus: Economic and Political Mastery
Henry's next masterstroke was the negotiation of the Intercursus Magnus in 1496, a comprehensive trade agreement with Duke Philip of Burgundy, son of Maximilian I. This treaty also had profound implications:
Economic Benefits: It restored and enhanced trade relations between England and Burgundy, benefiting merchants and bolstering the English economy.
Undermining Warbeck: As part of the agreement, Margaret of Burgundy had to cease support for Perkin Warbeck, stripping the pretender of a significant ally and resource base.
Diplomatic Leverage: The treaty demonstrated Henry's ability to balance economic interests with political strategy, securing his position at home and abroad.
Even with incomprehensible financial strain and pressure Henry held out on his imposed trade embargo against Burgundy for 3 years! By moving his trade route from Antwerp to Calais Henry could have completely collapsed his economy. However, the steadfast king held on with his signature steely patience no doubt white knuckling every letter from the discontent merchants.
In the end it paid off.
Duke Philip ceded to Henry’s demands. He no longer sat on his hands. He pressured Margaret to end support of Warbeck. Had she continued to support the pretender she could have faced:
Losing her coveted dower lands which she had fought for exhaustively in the previous decade
The drying up of the lucrative trade economy with England and resentment from nobility and merchants affected
Isolation from Duke Philip and Maximilian’s court which was a significant source of her influence
Legacy of a Strategic King
Can we all agree that Henry VII's actions during this tumultuous period exemplify the power of strategic diplomacy and unwavering resolve? Faced with external threats and complex political dynamics, he navigated challenges with caution, intelligence, and boldness when necessary.
While the reigns of Henry VIII and Elizabeth I dominate popular history, let’s not overlook the pivotal achievements of Henry VII. His strategic brilliance and political acumen as the 15th century drew to a close solidified the foundation of the Tudor dynasty. It’s time to give these often-overlooked triumphs the recognition they deserve:
Securing the Tudor dynasty, paving the way for the prosperity and influence of his successors.
Strengthening England's economy and international standing, setting foundations for future expansion.
Demonstrating the effectiveness of diplomacy over warfare, a lesson echoed throughout history.
Henry's legacy is that of a king who understood the intricate game of politics and played it masterfully, ensuring that England emerged stronger and more resilient in the face of formidable adversaries.
What do you think of Henry VII's diplomatic maneuvers? Do you see him as a cautious strategist, a bold risk-taker, or like me, both! Let me know in the comments
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Until then,
Fair Thee Well
Further reading and sources:
Henry VII and the Tudor pretenders, Nathen Amin - subscribe to the historian and author’s fantastic substack here
The Winter King, Thomas Penn
Calendar of State Papers Relating To English Affairs in the Archives of Venice, Volume 1, 1202-1509. Originally published by Her Majesty's Stationery Office, London, 1864. https://www.british-history.ac.uk/cal-state-papers/venice/vol1/pp226-252
I also really really enjoyed listening to both of these podcasts, the following episodes were well researched and very interesting on the Holy League and the history of Naples, Netherlands and all the complexities of the Holy League. Enjoy!
Tides of History:
History of the Netherlands
Fairtheewell, I enjoyed learning more about the people around Henry VII. Especially Maximilian’s involvements. I appreciate you sharing these. Hope you’re well this week? -Thalia
I found this so interesting! Particularly how I (not a Tudor expert!) often think he comes across in paintings as quite peaceful and passive, yet we have to remember that he must have been a fierce strategist, politician, and military leader to achieve all that he did. I'd love to hear more about his achievements: like you say, he is often overshadowed by his son and granddaughter, yet he arguably played a greater part in shaping the political stage than they did!