Rackham and Bonny also flee Nassau overland with their share of pearls. However when they are almost clean away, Rackham has a change of heart. He insists he wants to keep his name by going to Nassau to take the pardon. When Rackham attempts to garner a pardon, he is taken into custody. Rogers warns Rackham that if the pearls are not returned, the Spanish will invade.
Rackham eventually agrees to send a letter to Bonny seemingly instructing her to turn over the cache. However, he has secretly given Bonny instructions to take the cache and run. On learning that Governor Rogers has Rackham in their custody, the Spanish demand that both the gold and the man who stole it are handed over.
He prepares to deliver them to the Spanish, departing Nassau in a convoy accompanied by a large contingent of armed soldiers. Jack is banged up pretty badly, but alive, and he and Anne share a passionate kiss. Vane urges Flint to take the pearls and run ahead, while he frees Rackham from his chains. Billy Bones is sent back to Nassau to try and stir resentment towards Rogers and rescue Vane.
As they prepare for the English fleet to attack the island, Rackham asks Flint to command the Walrus during the battle. He persuades Teach join the fight. While the two fleets engage cannon fire, Bonny leads a boarding party swimming unnoticed to capture one of the English ships. They open fire on the rest of the fleet, forcing them to retreat. The victory may have won Rackham some respect from Teach. After their victory on the Maroon Island, Rackham and Bonny sails with Blackbeard as the pirates set their sights on retaking Nassau.
What was supposed to be an invasion of overwhelming force, only ends in disaster. Woodes Rogers continues to demonstrate his cunning, sinking ships as a hidden blockade to the harbour. However, Jack is blinded by the stars in his eyes when he stands on the quarterdeck next to Blackbeard; his ego demands he go down in history. However, Bonny confides that she no longer has any room in her heart for vengeance; not on Eleanor, nor on Max. Go after Rogers it is. Rogers springs his trap and a bloody battle ensues.
In the end, the unthinkable happens; Blackbeard is captured. Rackham watches helplessly from aboard The Revenge , and unfurls the white flag. In the aftermath, Jack and Bonny look on as Blackbeard is callously keelhauled three times, dragging him under the ship covered with razor sharp barnacles.
When Rogers learns that Nassau has fallen, he orders his lieutenant to take his sloop and deliver the pirates to Port Royal to hang. Milton bludgeon some of the pirates to death one by one. In the bloody brawl that follows, Bonny is almost pummelled to death, but desperately manages to grab the keys, and free her brethren.
They take the ship, but Bonny is left barely clinging to life. At sea, Featherstone wants to leave before the Spanish spots them, but Rackham opts to wait for anyone who survives the day. The two ships plan to head for the Maroon Island and regroup. Arriving in Philadelphia, Rackham plans to win Joseph Guthrie as a partner in imprisoning Rogers for causing the death of his granddaughter. However, Guthrie is in the company his respectable business partners, and shows him the door.
Rackham decides to bring Max to help make their case with Marion Guthrie. Jack Rackham must kill the one man who will continue the never-ending circle of violence in Nassau; James Flint. Recruiting an old sailor who once sailed with Avery , Jack makes it to the uncharted island, just as Rogers is leading the attack on the Walrus. After rescuing the survivors, Jack grudgingly allows Flint to take command of the pursuit of Rogers.
During the boarding, Rackham spots Rogers through the chaos, and the pair face-off. Rogers seems to be getting the upper hand, when Flint joins the fight.
Finally outmatched, Rogers is defeated and the pirates overtake the ship. Before the deal is struck, Rackham requests one more favour; to be involved in the writing of an affidavit against the disgraced Governor Rogers.
In the end, Nassau is a legitimate flourishing port under new Governor Augustus Featherstone, although the real power behind the throne is Max. While piracy is officially disapproved of, Rackham and Bonny still covertly sail under the black. Among their crew is a young kid by the name of Mark Read.
Rackham begins the series as the Quartermaster of the Ranger, and the brains behind captain Charles Vane's brawn. He is stylish, witty, well-read, and very proud of his wits, which he takes every opportunity to flaunt. However, Rackham is initially not a very good pirate. However over the series, he has proved time and again that he is very capable at what he does, culminating in his victory against an overwhelming English fleet at the Maroon Island.
Captain Vane as one of the few famous pirates that operated out of the pirate heaven and trading base " New Providence " located in the Bahamas. The rise of the influence of Jack Rackham happened in after Captain Vane decided to retreat after at the end of the long pirate run he confronted large French warship that was least twice of the size of The Ranger.
Vane was a seasoned sea commander at that time, and he saw that attacking such a large vessel was an impossibility for his small ship that recently went through several pirate raids and was in need of repair and resupply. The retreat caused discord in the crew, with Rackham taking charge in accusing Vane of poor decision making. In the end of the discussion, 15 crew members supported Vane in the retreat, while the other 75 argued that if captured the French vessel would not only bring them large riches but also a new base of operation that would enable them to become pirate crew with one of the largest and best-equipped ship in the Caribbean.
On November 24, , Rackham called to the vote in which Vane was removed from captaincy and branded as a coward. The crew promptly elected John "Calico Jack" Rackham to be a new captain of The Ranger, while Vane and his supporters were allowed to leave on a small ship carrying a supply of food and ammunition. After being promoted to a position of a captain, Calico Jack continued with the pirate runs that were mostly oriented toward smaller merchant and passenger transport vessels.
During one of his numerous runs he managed to gain control of the several larger ships, but the largest prize he ever managed to snatch happened to be from withing the holds of the large Jamaican vessel Kingston.
He fought and captured this vessel with skill, but sadly for him, this battle happened within sight of the Port Royal harbor, in view of all the government officials and merchants stationed there.
Outraged by the deeds of the now semi-notorious pirate, merchants in that city joined and outfitted pirate hunting Spanish ship with the task to capture and punish Captain Calico Jack. The events that followed were disputed by some historians, but eventual result was that Captain Jack and his crew managed to avoid the hunt.
According to the report written by the Captain Charles Johnson in his book "A General History of the Robberies and Murders of the most notorious Pyrates", John Rackham avoided Spanish pirate-hunting ship by taking advantage of the low tide that prevented Spanish warship from approaching anchored pirate sloop near the shore of the Cuba. During the night, Calico Jack and his crew managed to row with boats to the small sloop captured by the Spanish that was anchored near the warship.
They overpowered guards on it and sailed away, with Spanish Warship noticing the pirates were gone only in the morning when it was too late to pursue them. Other accounts of that tale tell of the different events where Spanish pursuers managed to ambush Calico Jack's flagship Kingston that was anchored near the Isla de Los Pinos off of Cuba. Rackham and most of his men avoided capture by hiding on the shore and waiting until pirate hunting ships left taking with them all their possessions, including all their rich plunder.
But, the affair was not over. On November 24, , Calico Jack branded Captain Vane as a coward, called for his removal and asked for a vote from the crew to see if they agreed. Overwhelmingly the pirates approved and Vane was removed from the captaincy, making Rackham the next captain.
The crew then set Vane and his 15 supporters adrift on a smaller boat, along with a small supply of ammunition and goods. Rackham and his men then cruised the West Indies and the waters near Bermuda plundering small vessels close to the shore. In December, Rackham and his crew captured a Jamaican merchant ship called the Kingston. The ship had a rich cargo and the crew made the new vessel their flagship. Unfortunately, the pirates had been seen and the outraged merchants of Port Royal hired bounty hunters to go after the thieves.
The bounty hunters caught up with the Kingston as it was anchored off Cuba in February The crew, in the meantime, were onshore and able to escape into the woods, but, they lost their ship and its cargo. Rogers provided a general amnesty and royal pardon for any pirate ready to accept it in exchange for discontinuing their illegal endeavors.
Captain Jack and his crew asked for the pardon, claiming that Captain Charles Vane had forced them to become pirates. Rogers, who hated Vane, granted the pardon and soon Rackham moved to New Providence. There, while frequenting the taverns, he met a woman named Anne Bonny.
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