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Brittany, here, is nowadays very much a part of France. It formally joined it in 1547, having been independent for roughly the previous 600 years. But given that Brittany's neighbor was much larger, far more powerful, and shared its only land border, how did Brittany manage to hold out for so long? Why didn't France take Brittany centuries earlier? To begin, as of the mid-8th century, Brittany was divided into numerous small states.

The Frankish kingdom next door realised that conquering the Britons there would be tough, and so instead they appointed 1 of the region's rulers to collect tribute from the rest on their behalf. This arrangement didn't last too long because several decades later Vikings. The raiding along the Frankish Empire's coast meant that its attention was needed elsewhere and so Brittany was free to rebel. This saw it gain some freedom for a short time because like everybody else in Northern Europe, they too had to deal with the Vikings. Like many other small states, Brittany wasn't able to resist and found itself ruled by Norsemen until the mid-ninth century.

This was when the grandson of the last independent Breton ruler, Alan, was aided by King Æthelstan of England in reconquering Brittany. He was successful and thus became its duke, with Brittany becoming independent. In the century after this Brittany was a mess of rebellions and despite its weakened state France never invaded, and the reason why was that the French nobles whose lands neighboured Brittany intermarried with Brittany's rebels and lords which made intervention a problem. Unsurprisingly it wasn't long until the rulers of Brittany were soon dealing with the kings of France personally, who were very interested in keeping the duchy in line. Their opponents at this time were of course the kings of England, and both royal houses competed for the duchy's friendship, and it was this competition that gave the duchy a much greater degree of independence than it could have hoped for normally.

Brittany's position meant that it was valuable for England to open up another front in a war against France if it needed to, and for France, robbing England of that ability was worth giving any loyal duke some extra freedoms. And after England lost the Hundred Years' War, the only major state with a stake in Brittany was France, which didn't make any plans to invade or reduce the Duchy's freedoms. So why? Well, first of all, France was broken exhausted and so launching an expedition which would cost money and also leave it hoping to attack from Spain or the Holy Roman Empire was a no-no. And at this point, if you couldn't conquer a land, there was always plan B.

Wait for the ruler to only have a daughter and marry her. Which is what happened in 1498 when Duke Francis II died, leaving only his daughter Anne to rule the Duchy. To protect the Duchy from France, it was agreed that Anne would marry the heir to the Holy Roman Empire, Maximilian von Habsburg. It couldn't be done in person because travel had its risks and so it was done remotely. This annoyed the King of France, Charles VIII, because he didn't want Brittany being ruled by his rival next door and so he politely asked for it to be annulled.

By which, I mean he invaded. After defeating the Bretons, Charles forced Anne to marry him and sent her to Paris and using his own nobles to run Brittany in her stead. The 2 didn't have any heirs, and so when Charles VIII opted to spend some time in the afterlife, Anne returned to Brittany. For like, 5 minutes, because Charles' successor and cousin Louis XII had the same quarrel with an independent Brittany, and so Anne was forced to marry again. This time, they did have children, and the eldest, Claude, was married to the next King of France, Francis I, whose son, Henry, would go on to inherit both the Duchy of Brittany and the Kingdom of France, at which point the title of Duke of Brittany was abolished and the lands thereafter were simply ruled by the King of France, thereby ending Brittany's 600-year streak of independence against France's wishes.

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