Comparing the Unwanted: Lord Walder Frey and Thomas Stanley

Mihaela Raileanu
5 min readJul 24, 2024

The Cunning Strategies of Walder Frey and Thomas Stanley

In the tumultuous medieval England, loyalty and treachery were intertwined, and those who adeptly navigated these troubled waters often rose to power or fell from grace. Two notable figures who excelled in the art of opportunism are Lord Walder Frey, a fictional character in George R.R. Martin’s Song of Ice and Fire series, and Thomas Stanley, a real-life English nobleman during the War of the Roses. Despite the separation of fiction and fact, both earned their reputations through cunning strategies and calculated decisions, carefully choosing sides according to the advantages they could gain.

Pete Linforth, Pixabay

House Tully called the unsympathetic lord “The late Walder Frey” because, during Robert Baratheon’s rebellion against House Targaryen, he hesitated to bring troops until it became clear on whose side victory would fall.

Walder Frey can be compared to Ralph Neville (see the article A Source of Inspiration for Walder Frey). Still, it is equally valid that Ralph Neville is not known to have ever hesitated to offer military support. George R.R. Martin could have had someone else in mind when he created old Walder Frey. But what?

Those with more knowledge of medieval history

may remember Margaret Beaufort’s fourth husband (none other than Henry VIII’s grandmother Henry VIII’s grandmother), Thomas Stanley.

Thomas Stanley, 1st Earl of Derby

Thomas Stanley was known for his political opportunism and habit of giving military support only to those who would win. Stanley first played this strategy in 1459, when the House of York faced Henry VI’s army. At that time, Stanley ignored the royal command, refusing to bring his forces to fight House York at Blore Heath.

The Battle of Blore Heath, original painting by Graham Turner

Moreover, Stanley was accused of not only failing to intervene on the wrong side. Worse still, he positioned his troops not far from the battle scene. When the time was right, Stanley had no problem sending his forces to fight on the side of the Yorks. Because they were clearly the winners. He did this not because he wanted to help the Yorkists but because he was interested in the advantages of such support. Cunning strategy, huh?

About ten years later,

when Warwick (nicknamed the Kingmaker) tried to oust Edward IV from the throne, Stanley was expected to join him with much-needed military forces. It was well known that Edward IV was the king who had never lost a battle and had no intention of losing that one. But when Warwick’s ally, Margaret of Anjou, was late arriving for a decisive battle, Stanley held his troops in place, and all was lost. For Warwick.

Stanley was also initially a loyal friend of Richard III

even though he was married to the mother of Richard’s enemy (Henry VII). However, in the summer of 1485, Stanley begged Richard to allow him to leave for his residence in the North. Richard gave him permission but kept Stanley’s son hostage to ensure his father’s good behavior. Later, hearing that Henry Tudor (the future Henry VII) had invaded Wales, Richard ordered Stanley to raise his men and join him immediately. Stanley did not, claiming that he was suffering from ‘sweating sickness,’ a condition that claimed many lives in those days. We all know how the Battle of Bosworth ended with King Richard III’s death and Henry VII’s accession (Henry Tudor).

When Richard III and Henry Tudor finally met at Bosworth

Stanley held his troops in place, intervening neither on Richard’s side nor on Henry’s until it was clear who would win. In any case, frustrated that Stanley did not intervene, Richard III threatened to kill his son. Stanley would have replied:

Sire, I have other sons.

This line is very reminiscent of Walder Frey’s response to Catelyn Stark when she threatened to kill his wife if he didn’t release his son:

I’ll get another wife!

Lord Frey and some of his daughters

This strategy made Stanley rich. After the Battle of Bosworth, Henry Tudor defeated Richard III, and he showed his gratitude to his stepfather (Stanley was married to Margaret Beaufort at the time) by making him an earl. Henry would later make Stanley the godfather of his heir.

However, more was needed for Stanley’s loyalty. After only 2 years, Stanley had no problem betraying Henry in favor of the pretender to the throne, Lambert Simnel. We can say that Thomas Stanley was a political realist and a survivor par excellence. At a time when loyalty was at a premium, Stanley waited until the very last moment before deciding whose side he was on. However, he did this not just to survive, but also to ingratiate himself with the victor. Or was this more about opportunism than survival?

In Stanley’s defense, it was tough to respect one alliance or another during the War of the Two Roses. Many nobles were caught, like Stanley, in the game of the powerful ambitions of the day. As Lord Frey said:

Stark, Tully, Lannister, Baratheon… Give me one good reason why I should waste a single thought on any of you.

Thomas Stanley is worth saying a little more about. Some believe he was the one who masterminded the murder of the Princes in the Tower, the two heir sons of King Edward IV.

Stanley controlled access to and from the Tower of London when the boys disappeared (probably murdered). Henry VII felt unsafe on the throne if the true heirs were alive. Thomas Stanley knew this; he had the motive and opportunity to commit the heinous crime.

Thomas Stanley and Lord Walder Frey remain symbols of extreme opportunism and pragmatism in history and literature. In an age when loyalty was often a scarce and volatile commodity, both demonstrated that survival and prosperity were usually reserved for those who could intelligently play the games of power. By comparing these two characters, we can better understand how the art of political treachery and manipulation was essential to success in times of uncertainty and rapid change. As Lord Frey pointed out, alliances and loyalties are often fleeting, and the true mastery lies in navigating those alliances to always come out on top.

In a comprehensive outline, this is Thomas Stanley, to whom the too cunning and ruthless Lord Walder Frey may be compared.

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Mihaela Raileanu
Mihaela Raileanu

Written by Mihaela Raileanu

Researcher, writer, explorer of ideas. I write about films (Lord of the Rings, Game of Thrones) and how we can create a better world. Join for fresh insights!

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