To challenge a king, he needed a vision. To rule like one, he needed ambition.

Let’s talk about Simon de Montfort—because he’s one of those historical characters who refuses to fit neatly into the box marked “hero” or “villain.” He was a French noble who married into the English royal family, led a rebellion against a king, and—whether by design, destiny, or both—helped lay the groundwork for England’s parliamentary tradition.

And then he was killed. Brutally. By the king’s son.

But we’re getting ahead of ourselves.

A Foreigner with Big Ideas

Simon wasn’t born English. He came from a powerful French family with crusader credentials and ambition to spare. In 1238, he married Eleanor, sister to King Henry III—a move that raised a few eyebrows and earned him the earldom of Leicester.

At first, he seemed loyal enough. But Henry’s reign was… not exactly smooth sailing. Extravagant spending, foreign advisers, and a knack for ignoring the barons didn’t win him many friends. De Montfort, initially an insider, became one of the loudest voices for reform.

The Rebel with a Council

In 1258, de Montfort and other barons forced Henry to accept the Provisions of Oxford—basically medieval checks and balances. It called for a council of barons to guide the king’s decisions. Sound familiar? It should. It was a baby step toward parliamentary government.

But Henry didn’t take kindly to being managed. The reforms faltered, and England slid toward civil war.

War, Power, and a Radical Parliament

By 1264, de Montfort was done talking. He raised an army and defeated the king at the Battle of Lewes, capturing both Henry and Prince Edward (yes, the future Edward I—the hammer of the Scots). Suddenly, de Montfort was England’s de facto ruler.

And in 1265, he did something extraordinary: he summoned a Parliament that, for the first time, included not just nobles and clergy, but knights and burgesses—representatives of towns and shires. Ordinary men. People who had never been invited into governance before.

It wasn’t democracy, but it was a shift. A ripple.

The Fall at Evesham

Simon’s rule didn’t last. He played favourites. He gave jobs to his sons. He alienated some of his own allies. Meanwhile, Prince Edward escaped captivity, raised an army, and met de Montfort at Evesham.

What happened there wasn’t a battle so much as a slaughter. Simon was outnumbered, surrounded, and killed. His body was hacked to pieces—his head displayed on a pike. Grisly, yes. But to some, he became a martyr. Pilgrims came to his grave at Evesham Abbey until the cult was shut down.

So Who Was He, Really?

That’s the complicated part. De Montfort was a reformer, no question. But also a power-seeker. A man who wanted to limit the king’s power—so he could wield it better himself. He fought for a voice for the people—but wasn’t above stacking the deck with his own kin.

He was, in other words, human.

But his 1265 Parliament planted a seed. Parliament would be suppressed, then reshaped, then reborn—but the idea that the king was not above the law had taken hold. And it never fully let go.

Legacy

Today, you won’t find Simon de Montfort’s face in portraits lining Tudor galleries. No Holbein, no armour-clad oil painting. But you will find his fingerprints on democracy—and his name carved into schools, universities, and the story of how England learned to question its kings.