Hello, reader! Longtime lurker, this was my attempt to create some kind of plausible timeline in which Francis Drake lives a bit longer and encounters the Maroon, or Cimarróne, people in the Caribbean. So, sit back, take a read if you will, and tell me if this is something that should be continued or buried under newer posts. Thanks!
The State of the Cimarrónes: 1594-1601
In 1594, King Phillip the Second of Spain had a problem. You see, a little Englishman had managed to use a few underhanded tricks and the fickle favor of the weather to destroy the single largest fleet in Spanish history and prevent the restoration of a Catholic monarch in England. He’d also raided Spanish ships carrying gold from the New World, killing the experienced sailors of King Phillip’s and ruining his plan of shipping vast hordes of gold he’d righteously obtained from the mines of Mexico back to the vaults of Spain. As if this wasn’t enough, Drake allegedly sent a letter to the Spanish King asking for the 20,000 ducats the monarch had placed on his life, since he “was in possession of it.” It was little stuff like that which really got under the skin of the “Most Catholic Monarch.”
It came as no surprise, then, that after failing to take Las Palmas in the Canary Islands, Sir Francis Drake returned to do what he did best - raiding Spanish territories in the New World, disrupting their shipping lanes in the Caribbean and generally causing mayhem. By this time, Drake’s little Armada was an eclectic group of men - primarily Englishmen on his flagship, the Golden Hind, but with a fair mix of Portuguese and Dutchmen from his failed attack on Lisbon six years earlier. They struck out for riches in the New World, and in 1596, they found them.
After briefly flirting with the idea to invade Puerto Rico, Drake instead decided to intercept a Spanish Treasure Fleet in Panama. After thoroughly ransacking them, he moved on to Santiago, an island he’d been told by the Spanish seamen was lightly guarded. Since lightly guarded coastlines and Francis Drake went together like a wounded Gazelle and a Lion, the English Privateer descended upon the island. Between August 16th and September 6th of 1596, Drake’s Privateers bounced around the island like a rolling ball of murder and pillaging.
It was on September 3rd, 1596, that a fateful meeting for the history of Santiago would take place. As Drake planned on retreating, he ran into a small group of raiders planning on attacking St. Jago de la Vela, the capital of Spanish Santiago, which the English raiders had inventively taken to calling “Spanish Town.” These raiders were not Drake’s men, dissatisfied Spaniards, or any other Europeans, for that matter. The Spaniards had taken to calling them Cimarrónes, runaway African slaves from the Spanish plantations that had mixed with the local Taíno population on the interior of Santiago. The Spaniards had a history of attacking these Cimarrónes for the crime of not being enslaved, and the Cimarrónes had taken to striking back, despite lacking the advantages of firearms, metal armor, artillery, and so on. Nevertheless, these spirited fighters had taken advantage of the English attack on Santiago, striking at the city of St. Jago de la Vela, hoping to strike a blow against the Spanish imperialists.
It just so happened that Drake had sailed towards St. Jago de la Vela’s harbor with the intention of plundering the city before retreating to England. When he saw the ferocity of the Cimarróne attack on “Spanish Town,” Drake remembered his experience working with similar people on the Spanish Main over two decades earlier - nothing makes friends like opposition to the Spanish.
With their mutual dislike of the island’s current owners as a uniting factor, the Privateers and Cimarrónes struck a fateful bargain. In exchange for half of the firearms possessed by the English (although Drake’s journal suggests that they may have only handed over about a third of their guns), including a single cannon from the Golden Hind, as well as powder, shot, and ten horses, the Cimarrónes agreed to ally themselves with the English. The deal was a mutually beneficial one, as Drake got to continue to harass the Spanish while he went back to England, while the Cimarrónes were better able to fight against their Spanish oppressors.
Drake’s ships returned to England, triumphant in that they had stolen Spanish gold and disrupted Spanish industry, but not knowing what they had started with their alliance with the Cimarrónes in the Caribbean.
Over 1597 and 1598, during which time Francis Drake lived it up in England before having to deal with a debilitating case of dysentery. In the meantime, the Cimarrónes continued their guerrilla war against the Spaniards in Santiago. Despite their new weapons, they faced a series of serious setbacks during those two years. In April of 1597, Spanish reinforcements arrived in Santiago, building defenses and being generally intelligent in their actions, instead of searching for riches as their Conquistador predecessors had done. This made it rather difficult for the Cimarrónes, what with their tribal nature, lack of cohesion, and small number of firearms, to carry out successful attacks against the Spanish.
In June of 1597, the Spanish forces on the island launched an expedition into the interior of Santiago, hoping to drive out the Cimarrónes. They moved through the jungle with 700 men, although the terrain made it impossible to bring large contingents of cavalry or artillery into the jungle. On June 18th, the Spanish force entered what had been the primary Cimarrónes village, only to discover that, shockingly, the people in the village had chosen not to let themselves be handed over (back over, in many cases) into slavery. The Spaniards destroyed the village and followed the trail to the band of African-Taínos.
The following week was, frankly, an utterly shitty one for the Spanish force. The first four days saw oppressive heat that led to the Spanish shedding the majority of their armor, while the 22nd, 23rd, and 24th saw near-constant rains, rendering the majority of the firearms possessed by both sides useless. On the morning of the 25th, an advance force of 300 Spaniards awoke to what was described by one of the few survivors as inhuman screaming. The first few minutes of the attack saw over 200 deaths, with close to 100% of those deaths being Spanish soldiers. The casualties were a drop in the bucket for the vast resources of the Spanish Empire, and even in Santiago, it was a relatively small loss. However, it did lead to the capture of a significant amount of firearms and iron weaponry, as well as a significant psychological blow to the Spanish forces in Santiago.
Despite this, there was still a difficult road ahead of the Cimarrónes. Their main village had been burnt by the Spanish, and it took most of 1598 to recuperate, with the construction of the town that would later become known as “New Haven,” as well as the creation of such mundane things as farms and houses for the people. This would be set back significantly by a second Spanish raid in 1598, this one satisfied with killing a few parties of men and selling a few dozen children into slavery before returning to the heavily Spanish coast. Still, the Cimarrónes were far more powerful than they had been before Sir Francis Drake’s arrival. The Spanish feelings about this could be summed up in a single word:
Fuck.
In 1599, a cockney sea dog by the name of Michael Geare arrived in Santiago, commanding the pinnacle James and, like his peer Drake, looking to cause trouble like the neighborhood ruffians that they were. If the Caribbean could have been considered a neighborhood, that is.
Geare arrived with his compatriot David Middleton and a crew of English Privateers to do what Englishmen in the 16th century did best and loot the area. He landed in Portland Bight, to the south of St. Jago de la Vela, and began to plan a sneak attack on the Spanish city through the jungles of the island. Unfortunately, he failed to realize that the past two years had seen the Spaniards prepare for exactly that method of attack - although they were expecting the attackers to be of a distinctly darker complexion than Geare and his scalawags. An aborted attack saw nearly 20 of Geare’s crew killed or abandoned and the remainder scattered in the jungle.
The largest group that escaped the debacle was composed of 11 men, including Michael Geare, five sailors, two cooks, and three veteran soldiers from the Dutch Wars. They soon found themselves captured by the Cimarrónes, who believed them to be Spanish soldiers. It was only Geare’s quick thinking, having heard of Drake’s interaction with the group, that saved the eleven lives. In exchange for their freedom, the Englishmen would hand over all of their guns, cannons, and gunpowder. It wasn’t the best deal for Geare and his compatriots, but they agreed nonetheless. Being propositioned in such a manner while tied up tends to make English Privateers more agreeable to such suggestions.
When Michael Geare returned to the James, however, he realized that eleven men were nowhere near enough to sail the Atlantic back to England, and that the rest of his crew was likely lost to severe cases of malaria, starvation, or Spanish bullets. Stuck in Santiago, he decided instead to utilize the James to make the most of his situation. Taking a group of Cimarrónes onto the James, he became the first English Sea Dog to raid in the service of Africans. Of course, with a full crew, one would think he’d just sail back to England, but according to his journal, he feared that the Cimarróne element of his crew would eat him alive if he attempted to return to Europe. Modern historians, however, doubt that the Cimarrónes were cannibals, and instead suggest that he would have been given the more civilized justice of a spear wound had he fled to England.
That said, Geare’s situation was not as bleak as it might have seemed. He and his Cimarróne first mate, Obi, an escaped slave from Cuba, reportedly became fast friends, launching daring raids on Spanish forces and, in January of 1600, the two and twenty-three other Englishmen and Cimarrónes attacked the Spanish dock of Ocho Rios under the cover of night, burning three ships in the harbor and making off with the fourth, a Spanish Galleon which the two christened the “Devil’s Dog.” All the while, New Haven continued to grow, until Geare offered to take three hundred Cimarrónes to the coast, where they could found their own port in which they could store the James and the Devil’s Dog. The town, known as Gearestown, was founded along the southern coast of Santiago, with Geare overseeing the construction of the docks, which he deliberately built enclosed by a palisade and ditch, just in case the Spaniards got any bright ideas. Bright ideas like his own attack on Ocho Rios, that is.
Geare would have been perfectly content with his little base of operations had he not been usurped by the biggest name in the Privateering industry, Sir Francis Drake. Having recovered from his dysentery, and at any rate always up for killing some Spaniards, Drake had heard rumors of Gearestown as a haven for English Privateers, and in July of 1600, the Golden Hind drew into harbor at Gearestown.
It should be noted that Gearestown was nothing particularly special as far as ports went. The docks had rudimentary defenses, and there were some houses that were certainly not structurally sound. To put it bluntly, a poor fishing village in Wales could put Gearestown to shame many times over. Nevertheless, most Privateers had to accept “any port in a storm,” and when that storm was an angry Spanish fleet, Gearestown would have to do.
Yes, there was a Spanish fleet headed towards Gearestown. Three Galleons, accompanied by ten pinnacles of varying sizes, they were commanded by Juan Maldonaldo Barnuevo, the Spanish Governor of Cuba, who was searching for the 20,000 ducats Phillip II had placed on Drake’s head. The Cimarrónes and Drake, whose successes had come from hit-and-run tactics, resolved to flee to fight another day, but Geare managed to stall them long enough to force them to stay and fight. Not out of heroism or stalwartness, but rather because he stood to lose a large amount of treasure if Gearestown fell. So, the two Privateers and a bunch of runaway slaves and natives had to fight off a small Spanish fleet.
Here, the distinction between as ship and a boat becomes important. While there’s no “official” definition of the difference, a ship has masts, sails, and requires lots of trees to construct. Generally, they’re what counts in a naval engagement, and Governor Barnuevo had these in abundance. A boat, on the other hand, has no source of movement other than the current, rowing, and other laborious activities. They are also usually far smaller than ships, and can be constructed out of a single tree. It would be boats that would decide the Battle of Gearestown.
Since it seems that one cannot teach old sea dogs new tricks, Drake resolved to replicate the winning tactics from his fight against the Spanish Armada twelve years earlier. On the night of August 2nd, 1600, thirteen hollowed-out logs filled with gunpowder were launched from the shore of Santiago, each with a single man rowing atop them and sporting a white flag. It being slightly after midnight, the Spanish guards assumed they were deserters coming to join the fleet and save their lives, and didn’t fire on the logs. When the impromptu fireships reached the sides of the Spanish pinnacles, the men lit fuses and dove into the water, swimming back to shore as quickly as possible. The plan was only partially successful - of the thirteen, five sank before they reached the Spanish ships, only three went off, and only seven men managed to make it back to shore, but the three explosions did manage to incapacitate two pinnacles and began to flood a third.
With that ruse at least minimally successful, Drake and Geare mounted their attack with the Golden Hind, James, and Devil’s Dog. The ships had shifted all of their cannons to a single side, firing a devastating broadside that raked the Spanish pinnacles with cannon-fire.
A few explosions and the broadside weren’t enough to turn the tide of the Spanish blockade of Gearestown, but an unexpected attack in the middle of the night, coupled with, according to several sources, the war cries of the Cimarrónes, unnerved the forces of the Spaniards, who turned heel and fled the scene, much to the chagrin of Governor Barnuevo, who slept through the event, and failed to see how the threat of being eaten by the Cimarrónes merited a full retreat. Apparently, it was common for Europeans to believe that anyone they didn’t recognize would eat them given half a chance.
The Battle of Gearestown is marked by many as the beginning of the independence of the Cimarrónes, so much so that it’s currently a national holiday in Santiago. This isn’t entirely accurate, however. They had managed to throw back a Spanish fleet, but the war with the Spaniards was only half-over. The battle for Santiago was only just beginning, and in the years to come, the Cimarrónes and Englishmen would battle with the Spanish fleet over the island, and would result in the shattering of the Spanish domination in the Caribbean.
For Michael Geare, however, it was time to get back to work. With the Devil’s Dog and a seasoned crew, he ventured off, sailing for England with a Cimarróne ambassador in tow and a plan to win himself fame in the New World.
The State of the Cimarrónes: 1594-1601
In 1594, King Phillip the Second of Spain had a problem. You see, a little Englishman had managed to use a few underhanded tricks and the fickle favor of the weather to destroy the single largest fleet in Spanish history and prevent the restoration of a Catholic monarch in England. He’d also raided Spanish ships carrying gold from the New World, killing the experienced sailors of King Phillip’s and ruining his plan of shipping vast hordes of gold he’d righteously obtained from the mines of Mexico back to the vaults of Spain. As if this wasn’t enough, Drake allegedly sent a letter to the Spanish King asking for the 20,000 ducats the monarch had placed on his life, since he “was in possession of it.” It was little stuff like that which really got under the skin of the “Most Catholic Monarch.”
It came as no surprise, then, that after failing to take Las Palmas in the Canary Islands, Sir Francis Drake returned to do what he did best - raiding Spanish territories in the New World, disrupting their shipping lanes in the Caribbean and generally causing mayhem. By this time, Drake’s little Armada was an eclectic group of men - primarily Englishmen on his flagship, the Golden Hind, but with a fair mix of Portuguese and Dutchmen from his failed attack on Lisbon six years earlier. They struck out for riches in the New World, and in 1596, they found them.
After briefly flirting with the idea to invade Puerto Rico, Drake instead decided to intercept a Spanish Treasure Fleet in Panama. After thoroughly ransacking them, he moved on to Santiago, an island he’d been told by the Spanish seamen was lightly guarded. Since lightly guarded coastlines and Francis Drake went together like a wounded Gazelle and a Lion, the English Privateer descended upon the island. Between August 16th and September 6th of 1596, Drake’s Privateers bounced around the island like a rolling ball of murder and pillaging.
It was on September 3rd, 1596, that a fateful meeting for the history of Santiago would take place. As Drake planned on retreating, he ran into a small group of raiders planning on attacking St. Jago de la Vela, the capital of Spanish Santiago, which the English raiders had inventively taken to calling “Spanish Town.” These raiders were not Drake’s men, dissatisfied Spaniards, or any other Europeans, for that matter. The Spaniards had taken to calling them Cimarrónes, runaway African slaves from the Spanish plantations that had mixed with the local Taíno population on the interior of Santiago. The Spaniards had a history of attacking these Cimarrónes for the crime of not being enslaved, and the Cimarrónes had taken to striking back, despite lacking the advantages of firearms, metal armor, artillery, and so on. Nevertheless, these spirited fighters had taken advantage of the English attack on Santiago, striking at the city of St. Jago de la Vela, hoping to strike a blow against the Spanish imperialists.
It just so happened that Drake had sailed towards St. Jago de la Vela’s harbor with the intention of plundering the city before retreating to England. When he saw the ferocity of the Cimarróne attack on “Spanish Town,” Drake remembered his experience working with similar people on the Spanish Main over two decades earlier - nothing makes friends like opposition to the Spanish.
With their mutual dislike of the island’s current owners as a uniting factor, the Privateers and Cimarrónes struck a fateful bargain. In exchange for half of the firearms possessed by the English (although Drake’s journal suggests that they may have only handed over about a third of their guns), including a single cannon from the Golden Hind, as well as powder, shot, and ten horses, the Cimarrónes agreed to ally themselves with the English. The deal was a mutually beneficial one, as Drake got to continue to harass the Spanish while he went back to England, while the Cimarrónes were better able to fight against their Spanish oppressors.
Drake’s ships returned to England, triumphant in that they had stolen Spanish gold and disrupted Spanish industry, but not knowing what they had started with their alliance with the Cimarrónes in the Caribbean.
Over 1597 and 1598, during which time Francis Drake lived it up in England before having to deal with a debilitating case of dysentery. In the meantime, the Cimarrónes continued their guerrilla war against the Spaniards in Santiago. Despite their new weapons, they faced a series of serious setbacks during those two years. In April of 1597, Spanish reinforcements arrived in Santiago, building defenses and being generally intelligent in their actions, instead of searching for riches as their Conquistador predecessors had done. This made it rather difficult for the Cimarrónes, what with their tribal nature, lack of cohesion, and small number of firearms, to carry out successful attacks against the Spanish.
In June of 1597, the Spanish forces on the island launched an expedition into the interior of Santiago, hoping to drive out the Cimarrónes. They moved through the jungle with 700 men, although the terrain made it impossible to bring large contingents of cavalry or artillery into the jungle. On June 18th, the Spanish force entered what had been the primary Cimarrónes village, only to discover that, shockingly, the people in the village had chosen not to let themselves be handed over (back over, in many cases) into slavery. The Spaniards destroyed the village and followed the trail to the band of African-Taínos.
The following week was, frankly, an utterly shitty one for the Spanish force. The first four days saw oppressive heat that led to the Spanish shedding the majority of their armor, while the 22nd, 23rd, and 24th saw near-constant rains, rendering the majority of the firearms possessed by both sides useless. On the morning of the 25th, an advance force of 300 Spaniards awoke to what was described by one of the few survivors as inhuman screaming. The first few minutes of the attack saw over 200 deaths, with close to 100% of those deaths being Spanish soldiers. The casualties were a drop in the bucket for the vast resources of the Spanish Empire, and even in Santiago, it was a relatively small loss. However, it did lead to the capture of a significant amount of firearms and iron weaponry, as well as a significant psychological blow to the Spanish forces in Santiago.
Despite this, there was still a difficult road ahead of the Cimarrónes. Their main village had been burnt by the Spanish, and it took most of 1598 to recuperate, with the construction of the town that would later become known as “New Haven,” as well as the creation of such mundane things as farms and houses for the people. This would be set back significantly by a second Spanish raid in 1598, this one satisfied with killing a few parties of men and selling a few dozen children into slavery before returning to the heavily Spanish coast. Still, the Cimarrónes were far more powerful than they had been before Sir Francis Drake’s arrival. The Spanish feelings about this could be summed up in a single word:
Fuck.
In 1599, a cockney sea dog by the name of Michael Geare arrived in Santiago, commanding the pinnacle James and, like his peer Drake, looking to cause trouble like the neighborhood ruffians that they were. If the Caribbean could have been considered a neighborhood, that is.
Geare arrived with his compatriot David Middleton and a crew of English Privateers to do what Englishmen in the 16th century did best and loot the area. He landed in Portland Bight, to the south of St. Jago de la Vela, and began to plan a sneak attack on the Spanish city through the jungles of the island. Unfortunately, he failed to realize that the past two years had seen the Spaniards prepare for exactly that method of attack - although they were expecting the attackers to be of a distinctly darker complexion than Geare and his scalawags. An aborted attack saw nearly 20 of Geare’s crew killed or abandoned and the remainder scattered in the jungle.
The largest group that escaped the debacle was composed of 11 men, including Michael Geare, five sailors, two cooks, and three veteran soldiers from the Dutch Wars. They soon found themselves captured by the Cimarrónes, who believed them to be Spanish soldiers. It was only Geare’s quick thinking, having heard of Drake’s interaction with the group, that saved the eleven lives. In exchange for their freedom, the Englishmen would hand over all of their guns, cannons, and gunpowder. It wasn’t the best deal for Geare and his compatriots, but they agreed nonetheless. Being propositioned in such a manner while tied up tends to make English Privateers more agreeable to such suggestions.
When Michael Geare returned to the James, however, he realized that eleven men were nowhere near enough to sail the Atlantic back to England, and that the rest of his crew was likely lost to severe cases of malaria, starvation, or Spanish bullets. Stuck in Santiago, he decided instead to utilize the James to make the most of his situation. Taking a group of Cimarrónes onto the James, he became the first English Sea Dog to raid in the service of Africans. Of course, with a full crew, one would think he’d just sail back to England, but according to his journal, he feared that the Cimarróne element of his crew would eat him alive if he attempted to return to Europe. Modern historians, however, doubt that the Cimarrónes were cannibals, and instead suggest that he would have been given the more civilized justice of a spear wound had he fled to England.
That said, Geare’s situation was not as bleak as it might have seemed. He and his Cimarróne first mate, Obi, an escaped slave from Cuba, reportedly became fast friends, launching daring raids on Spanish forces and, in January of 1600, the two and twenty-three other Englishmen and Cimarrónes attacked the Spanish dock of Ocho Rios under the cover of night, burning three ships in the harbor and making off with the fourth, a Spanish Galleon which the two christened the “Devil’s Dog.” All the while, New Haven continued to grow, until Geare offered to take three hundred Cimarrónes to the coast, where they could found their own port in which they could store the James and the Devil’s Dog. The town, known as Gearestown, was founded along the southern coast of Santiago, with Geare overseeing the construction of the docks, which he deliberately built enclosed by a palisade and ditch, just in case the Spaniards got any bright ideas. Bright ideas like his own attack on Ocho Rios, that is.
Geare would have been perfectly content with his little base of operations had he not been usurped by the biggest name in the Privateering industry, Sir Francis Drake. Having recovered from his dysentery, and at any rate always up for killing some Spaniards, Drake had heard rumors of Gearestown as a haven for English Privateers, and in July of 1600, the Golden Hind drew into harbor at Gearestown.
It should be noted that Gearestown was nothing particularly special as far as ports went. The docks had rudimentary defenses, and there were some houses that were certainly not structurally sound. To put it bluntly, a poor fishing village in Wales could put Gearestown to shame many times over. Nevertheless, most Privateers had to accept “any port in a storm,” and when that storm was an angry Spanish fleet, Gearestown would have to do.
Yes, there was a Spanish fleet headed towards Gearestown. Three Galleons, accompanied by ten pinnacles of varying sizes, they were commanded by Juan Maldonaldo Barnuevo, the Spanish Governor of Cuba, who was searching for the 20,000 ducats Phillip II had placed on Drake’s head. The Cimarrónes and Drake, whose successes had come from hit-and-run tactics, resolved to flee to fight another day, but Geare managed to stall them long enough to force them to stay and fight. Not out of heroism or stalwartness, but rather because he stood to lose a large amount of treasure if Gearestown fell. So, the two Privateers and a bunch of runaway slaves and natives had to fight off a small Spanish fleet.
Here, the distinction between as ship and a boat becomes important. While there’s no “official” definition of the difference, a ship has masts, sails, and requires lots of trees to construct. Generally, they’re what counts in a naval engagement, and Governor Barnuevo had these in abundance. A boat, on the other hand, has no source of movement other than the current, rowing, and other laborious activities. They are also usually far smaller than ships, and can be constructed out of a single tree. It would be boats that would decide the Battle of Gearestown.
Since it seems that one cannot teach old sea dogs new tricks, Drake resolved to replicate the winning tactics from his fight against the Spanish Armada twelve years earlier. On the night of August 2nd, 1600, thirteen hollowed-out logs filled with gunpowder were launched from the shore of Santiago, each with a single man rowing atop them and sporting a white flag. It being slightly after midnight, the Spanish guards assumed they were deserters coming to join the fleet and save their lives, and didn’t fire on the logs. When the impromptu fireships reached the sides of the Spanish pinnacles, the men lit fuses and dove into the water, swimming back to shore as quickly as possible. The plan was only partially successful - of the thirteen, five sank before they reached the Spanish ships, only three went off, and only seven men managed to make it back to shore, but the three explosions did manage to incapacitate two pinnacles and began to flood a third.
With that ruse at least minimally successful, Drake and Geare mounted their attack with the Golden Hind, James, and Devil’s Dog. The ships had shifted all of their cannons to a single side, firing a devastating broadside that raked the Spanish pinnacles with cannon-fire.
A few explosions and the broadside weren’t enough to turn the tide of the Spanish blockade of Gearestown, but an unexpected attack in the middle of the night, coupled with, according to several sources, the war cries of the Cimarrónes, unnerved the forces of the Spaniards, who turned heel and fled the scene, much to the chagrin of Governor Barnuevo, who slept through the event, and failed to see how the threat of being eaten by the Cimarrónes merited a full retreat. Apparently, it was common for Europeans to believe that anyone they didn’t recognize would eat them given half a chance.
The Battle of Gearestown is marked by many as the beginning of the independence of the Cimarrónes, so much so that it’s currently a national holiday in Santiago. This isn’t entirely accurate, however. They had managed to throw back a Spanish fleet, but the war with the Spaniards was only half-over. The battle for Santiago was only just beginning, and in the years to come, the Cimarrónes and Englishmen would battle with the Spanish fleet over the island, and would result in the shattering of the Spanish domination in the Caribbean.
For Michael Geare, however, it was time to get back to work. With the Devil’s Dog and a seasoned crew, he ventured off, sailing for England with a Cimarróne ambassador in tow and a plan to win himself fame in the New World.
