The Birth Of The British Republic

Here's a WI that most Americans (and probably some British) probably haven't thought of (or knew) a whole lot about:

What if Simon de Montfort's rebellion against Henry III had somehow succeeded? According to Wikipedia:

After the rebellion of 1263 and 1264, de Montfort became de facto ruler of England and called the first directly elected parliament in medieval Europe. For this reason, de Montfort is regarded today as one of the progenitors of modern parliamentary democracy.

Would a Republican England had managed to survive in the 13th Century? Or would de Montfort have become a Cromwell-esque dictator, starting yet another civil War?

(I just read about this myself, so I hope you'll excuse any hubris or ignorance in my fantasy :))
 
I doubt England would've become a Republic, or even remotely democratic. The Parliament summoned at this time wasn't particularly democratic at this time since it was mostly limited to landowners. Also considering Montforts royal connections (he was married to Eleanor of England), he would probably angle to set himself up as King, more than anything else.
 
I sincerely doubt the de Montfort was interested in any sort of Republic, despite his attachment to popularly elected representatives; he assumed power in England because he regarded the current King as intolerably incompetent. He never attempted to take the throne for himself, or to disinherit Prince Edward. If you'd like an earlier, more democratic or more radical Parliament from this, though, the key is de Montfort's relationship with Prince Edward. You probably need to have King Henry die at an opportune moment, although how you get young King Edward to trust and admire his Lord Steward I'm not really sure. Alternately, you can have Edward die young; his younger brother Edmund has clear title to the throne but probably is too young, and before that point has too few personal estates, to govern in opposition to de Monfort's Parliament.
 
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