The H Files by Helen Castor

The H Files by Helen Castor

The Art of the Deal

Richard II enters the Hundred Years War

Jun 16, 2026
∙ Paid
Upgrade to paid to play voiceover
Richard II’s arms, showing the cross and martlets of Edward the Confessor and the fleurs-de-lis of France as well as the lions of England, from the Wilton Diptych, c. 1396

Historians have to listen hard to their sources. Often, that means searching for nuance and subtext. Always, it means understanding context. Sometimes, it means hearing what’s actually been said.

And that presents a particular kind of challenge when what’s been said seems to make no sense.

The job of a historian is to make sense of things: to piece together evidence into a comprehensible shape, and then narrate, analyse and explain what it shows. And because our job is to make sense, we have an inbuilt predisposition to suppose there’s sense to be made in what we’re looking at, if we can only find it. The rational explanation must be there somewhere, we think, rationally.

Which brings me to 1395, and what I’m calling Richard II’s entry into the Hundred Years War between England and France.

The H Files by Helen Castor is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber – thank you.

In 1395 Richard was twenty-eight, and had been king of England for eighteen years. Of course that means he was already ‘in’ the war, and had been since he was ten.

(Also of course, no one then knew it was the Hundred Years War they were fighting – although by 1395, more than fifty years in, it was already the case that few people could remember a time before the whole thing started.)

But the main impression Richard had given so far was that he would much prefer not to be involved, if that was quite all right with everyone else.

At eighteen, when he was taken on campaign against France’s ally Scotland, he hated it, threw a tantrum, and insisted on going home. At nineteen, when a French armada was preparing to invade, he refused to engage with criticism in parliament other than by furiously threatening to ask his ‘cousin of France’ for help against his own angry and frightened subjects.

All in all, the writing had been on the wall since he was sixteen (the same age, we might note, as his father the Black Prince when he won his spurs and his heroic reputation at Crécy). In 1383 a planned expedition to rescue Flanders from the French had fallen apart because, as one chronicler laconically put it, ‘Rex laborare noluit’. To contemporaries, the Latin verb ‘laborare’ could mean ‘to travel’ as well as ‘to work’. A fair translation covering the entire debacle, therefore, might be ‘the king didn’t want to go’.

From 1389, however, it became clear that Richard still didn’t want to do the work even when the work wasn’t fighting, but negotiating for peace. In that year the war sputtered to a halt through the first in what proved to be a series of truces. The question remained: could a permanent settlement be reached?

For the next four years, Richard’s uncle John of Gaunt did everything he could to find some basis for agreement with the French. It was hard diplomatic labour. The issues at stake were deep-seated and complex. Would the English king give up his title to the crown of France, as claimed by Richard’s grandfather Edward III back in 1340? If so, what would he demand in return? Since the twelfth century English kings had been dukes of Aquitaine in southwestern France, and those territories were also in military and political play. Where should the borders of Aquitaine be drawn? Should the English king hold the duchy in full sovereignty, or did being Aquitaine’s duke make him a vassal of the king of France? If the latter was the case, did that mean he could be summoned to appear in the French king’s courts, or to do military service in his wars? If so, how on earth would that work in any future dispute between France and England?

None of these questions had easy answers – but Gaunt put his shoulder to the wheel. Little by little, he built constructive relationships with his opposite numbers in France. In 1393 they thrashed out a roadmap: by its terms, England would hold a generously drawn version of the duchy of Aquitaine in return for acknowledging French sovereignty over it. There were lots of thorny details yet to be worked out. Still, it was more progress towards peace than had been made in thirty years.

But, back in England in 1394, it turned out that the war had gone on too long and cost far too much, in both blood and money, for Gaunt’s countrymen to trust that he had found a way to end it without betraying England’s interests. The parliament summoned that spring would only accept the settlement with a string of conditions and modifications that left the proposals in ruins.

Gaunt salvaged another four-year truce from the rubble, and left for Aquitaine for a year. When more French envoys arrived at Westminster in 1395, therefore, Gaunt wasn’t there to meet them.

Richard had never before shown any interest in the detail of these protracted negotiations or the complex questions they raised. But this time the French delegation came with a much more personal proposal. Richard’s queen, Anne of Bohemia, had died in 1394. Should his next wife be one of the French king’s daughters?

Charles VI of France, detail from the Goldenes Rössl, 1405

The oldest of the French princesses was only five, but that did nothing to put Richard off. He loved the idea of a grand matrimonial alliance with a sovereign he’d always seen, despite the bloody realities of war and the pressing need to defend England’s geopolitical interests, more as a counterpart than an enemy.

And Gaunt’s absence left Richard to take direct charge of diplomacy for the very first time. The English embassy he sent to Paris in the summer of 1395 was led by two of his personal protégés, his twenty-two-year-old cousin Edward, earl of Rutland, and his childhood friend Thomas Mowbray, the twenty-nine-year-old earl of Nottingham. These young men were empowered not only to negotiate the king’s marriage to the little princess, but also to conclude a peace settlement on entirely new terms.

The size of the dowry Richard wanted along with his tiny bride was startling. His envoys were to open with a demand for two million gold francs – that is, more than £330,000 (at a time when Gaunt, who was rich beyond the wildest dreams of any other English nobleman, enjoyed an annual landed income of about £10,000). Still, it was clearly an opening gambit rather than a bottom line. If the French wouldn’t go for two million, Rutland and Mowbray were authorised to drop the price to one million, to be paid in instalments over the next four years.

However, if the dowry terms were startling, the instructions about the basis for a peace deal – to quote a historian who has written in thoughtful detail about these negotiations – ‘can only be described as breathtaking’.1

User's avatar

Continue reading this post for free, courtesy of Helen Castor.

Or purchase a paid subscription.
© 2026 Helen Castor · Privacy ∙ Terms ∙ Collection notice
Start your SubstackGet the app
Substack is the home for great culture