The date is September 12, 1721. Jolly leads a massive invasion of Tortuga during a Meeting of the Guilds in an attempt to wipe out the Marceline guild and its protectors once and for all. As the ships begin to arrive, pirates, navy, and EITC alike grab their sword hilts and and run to the beaches. The townsfolk quickly construct barricades at strategic locations on the island. They Wait... Suddenly they hear a booming voice scream " FIND ME JACK SPARROW! KILL THE PIRATES, SLAUGHTER THE ENTIRE TOWN, BURN IT TO THE GROUND! LEAVE NO SURVIVORS! " The undead hordes come upon the pirates with such ferocity that several inexperienced pirates are overwhelmed and slain on the spot. Their lines crumble and eventually, they are forced to fall back to the barricades. There, several groups of less than 100 pirates each all around the island make a stand at the barricades. They are magnificent. Some pirates are so powerful and mighty they take on a dozen undead at a time. Little do they know that the tide of the battle will soon turn drastically, towards Jolly's favor...
Jack Swordmenace hears screams coming from the graveyard. " What in the seven seas is going on here?", he asks. Suddenly, the ground comes alive with skeletons emerging from the ground and chasing after him. Jack grabs the hilt of his broadsword and when the skeletons grow near him, he draws his sword and slays 4 undead in a single stroke. But suddenly, at least 50 undead have emerged and are sprinting towards the lone man. Out of nowhere, a group of some two dozen pirates and soldiers ambush the undead from the trees as they chase Swordmenace towards the Faithful Bride. " We'll hold them off, get to the beach and lead the men!"
When Jack arrives at the Beach, the scene is horrendous. Dead pirates lay everywhere, and bones of the undead are so numerous that Jack couldn't take one step without stepping on a bone. A small group of some 43 navy soldiers and around 30 pirates are fiercely fighting undead off near a cluster of chairs and wagons that form a makeshift barricade. Jack draws his broadsword and engages a small group of undead, impaling them. He steps in and together, they slay the undead. However, suddenly, a voice is heard. " NEXT BRIGADE, ATTACK!" The worst was yet to come....
After countless hours of fighting the pirates and soldiers feel all is lost. With moral low and many dead, the pirates realize the only way most of them would be getting of the island was in a body bag. The barricades are overwhelmed and the surviving pirates and soldiers flee into the plaza of the Faithful bride, rallying around one last barricade and holding the undead off, who at this point had them surrounded on all sides, cut off from any reinforcements. After some fighting, the men guarding the entrances were slain by Spanish and French skeletons, and the undead infiltrated the plaza. The siege became a one on one struggle to defend the tavern. Jack hacked and slashed his way through the battlefield, occasionally pulling his repeater pistol and firing a few rounds at skeletons at point blank range. " WE HAVE TO BREAK THIS SIEGE! PUSH THEM BACK! " Just then, they hear ferocious explosions at sea. The Navy had come! A group of some 7 Man of War had engaged Jolly's fleet, and since they had caught them by surprise, were able to sink almost all of the Undead ships. Seeing this, the pirates morale soared and they began to fight like demons. Jack Swordmenace leads the defense force and together they manage to force the skeletons to retreat out of the plaza, the pirates waste no time to purse, cutting the skeletons down in the hundreds. Suddenly, the same booming voice of Jolly Roger, now infuriated, is heard. " MUST I DO EVERYTHING MESELF?! FOOLS!!" Jolly sprints to the edge of his ship, jumps off and hits the ground running, slashing his way to the Faithful Bride. He shoves against a large piece of wood that a group of pirates have placed to block the entrance, over powering them and shooting them as they lay on the ground. Just then, Jack draws his Sacred Repeater and let's out a shot, which grows straight through Jolly's eye and through his head. Clutching his head in agony, Jolly is defenseless. Jack siezes the opportunity and draws his Sacred Saber, driving it deep into Jolly's heart. Jolly shouts in pain and dissolves into the mist, still alive, though badly hurt.
The skeletons begin to flee, but the Navy has by now sunk the entire undead fleet. With nowhere to go, they panic, running around in circles and screeching. Groups of townsmen and pirates wielding muskets pick them off from the rooftops. And thus ends the Legend of the Longest Siege in History.
Ultimately, the siege would have a dramatic aftermath. After the battle, at least 400 pirates lay dead, hideously slaughtered by the undead. The entire undead army of over 20,000 lies lifeless on the ground. The Undead fleet of over a dozen ships lays on the ocean floor, along with several navy flag ships. It is a sad victory.