Siege of Middleton (1407)

The 1407 Seige of Middleton was the second of several conflicts between the inhabitants of Middleton and groups of Barbary Corsairs. Ali Karam led a force of some 500 corsairs against 50 fighting men of the Middleton Watch commanded by Pero Entenza and supported by some 200 townsmen. The battle is noted for the heroism and ascension to power of Sergeant Phillipe Cadron.

Background
In 1407 Middleton was the only town on Middleton Island, technically a part of Brunant but with little interaction. The Corsairs, due to their conflicts with the Venetian influenced Brunant,  were looking for a base of operations close to Brunant. Middleton Island appealed for several reasons: It had a population (roughly 1000 in Middleton town and several hundred in the surrounding area) small enough to be easily controlled but large enough to support the pirates if neccesary; It was a small enough island to be defensible; and it was surrounded by cliffs leaving only two easy landing points (Middleton Harbour and Hindon beach) which could be easily defended.

Brunant
By 1407 Brunant was facing it's first signs of internal instability. Karam believed (correctly) that Brunantian military would be unwilling to send assitance to Middleton, preventing a repeat of 1388. It was thus that Karam set out towards Middleton in September 1407 with 1 galley, 2 fustas and several small ships.

Battle
A fisherman with keen eyes managed to give the Men of Middleton more than an hour of warning. By the time Karam arrived in Middleton Harbour, Entenza and the 50 men of the watch stood ready to defend the city walls, supported by a growing number of poorly armed townsmen. Those inside the walls were forced to watch as Karam and his men made quick work of the people and the single ship left outside the walls. Realising that he had lost the element of surprise, Karam set up camp outside the walls, not bothering to set up seige for the people of Middleton had nowhere to flee to. The next morning Karam called the first attack on Middleton. Middleton's defenders fought valiently and held out for two days, suffering fewer injuries than the pirates.

Counter Attack
After 2 days the town defenders were exhausted and, despite inflicting heavier losses on the corsairs, the odds of victory were growing increasingly slimmer. Entenza's lieutenant Phillipe Cadron suggested a counter attack as a desperate measure, but Entenza chose to commit all his men to the defense of the town. Seeing sure defeat at the hands of the far superior corsair forces, Cadron went against orders and prepared for a counter attack. Unable to command men of the watch, Cadron was forced to recruit the from the supporting townsmen, ultimately recruting 30 poorely equipped men. As the sun rose and the pirates prepared to attack, Cadron and his men left the city. At 9am Karam launched his attack and by 11am the corsairs had breached the wall. Two counters, the second led by Entenza, failed to dislodge them and Entenza was seriously injured. With their Captain injured, their Lieutenant nowhere to be found and a breached wall, the defenders of Middleton quickly fell back. It was at this moment that Cadron launched his counter attack. With the element of surprise, Cadron's men had quickly dispatched the 20 corsairs left to guard the ships. With their lack of training and equipment this was no small feat, and their success was mainly due to the ferocity of Cadron and Isabella Hortiz, a woman who, disguised as a man, had joined the force. They now set about lighting the ships on fire, scoring a particular victory on one of the Fusta's which was full of gunpowder. The explosion on the Fusta was enough to draw the attraction of the corsairs to their ships, which by now were blazing heavily. The twenty men who had been left guarding the camp attacked Cadron, but again Cadron's men dispatched of them, Isabella being said to have killed 4 men herself, saving Cadron's life before succumbing to mortal wounds. Karam knew he could not afford to lose his ships, even a few of them, for that would leave him stranded and exposed to any Brunantian action that might eventually occur. With the fires as they were, he ordered 200 men to the ships to save them. Apparently watching the corsairs withdraw, Sergeant Alfons Cabra led a coutner attack. Depsite still facing an equal number of better trained and equipt pirates, the defenders of Middleton managed to drive them from the town, at great cost. Meanwhile the other pirates had managed to save all but one of the small ships, although one of the fustas was hardly water-worthy. Cadron and his surviving men had escaped into the wilderness and quickly returned to the town. Cadron was quickly hailed as a hero and when the injured Entenza, despite showing signs of recovery, died, apparently due to his wounds, Cadron became Captain of the Watch.

Victory
With just over 300 men left and having lost one ship and having another invalidated, the gains to be had from victory were quickly being outweighed by the costs. The following day Karam led the final assault on Middleton. The defenders, led by the corageous Cadron and Alfons, held their positions and after Karam was injured, allegedly by Alfons, the pirates withdrew. Now lacking sufficient men to both guard the ships and assault the town, Karam called an end to the attack and the next day the pirates sailed away to the cheers of the townspeople.