Five sleek rundown galleys were haphazardly docked on an otherwise desolate coast mid-way between the cities of Pentos and Myr. Their flags didn't carry any kind of skulls on them but anyone with even an iota of common sense could see that they were all pirate ships.
At the moment, most of the crew were standing in the shade of a few trees with only one large man with a crooked hat sitting comfortably on a light wooden chair.
"Where are they? Where are all the fucking ships laden with goods that you promised me, Huh?" Captain Jack growled, his hands gripping the handle of the chair so tightly that it almost crushed them. The sun was about to set for the third time since they had laid an ambush here in this god-forsaken place to wait for the prey... but their target was still nowhere in sight.
Most of the nearby pirates hurriedly scurried away from the center leaving behind two shivering pirates, Frank and his nephew, in the middle to take on the wrath of the Captain.
The Captain looked like a typical pirate with a hat, an eyepatch and a gold tooth and while he wasn't completely insane like some of the other famous pirates, he was still an... unpredictable man. One minute he could be singing and drinking with you and in the next something would set him off and he would dump you into the ocean while laughing his ass off. So the crew usually tried their hardest to not run afoul of his temper because when he gets angry, it is very... ugly.
"M-Maybe they got d-delayed, Captain—" Frank stammered as he tried to come up with some way to wiggle out of the situation but the Captain didn't have much patience for him.
"Shut up!! I've had enough of yer excuses!!" Captain Jack thundered as he slowly rose from his seat. He was a massive man, almost a head taller than everyone else, so when he came to stand before the two pirates they almost pissed their pants, "You told me that seven ships left Bravoos laden with goods with less than 100 fighters on board and that they would be here soon... So where the fuck are they!! I've been sitting on my ass here for three fucking days with not a single ship in sight. Which means that you lied to me and there were no such ships to begin with because no matter how delayed they are, it can't take them more than three days to reach here from Pentos..."
Unlike what most people think, being a pirate involves a lot more than just drinking, sailing and looting. A lot of delicate intelligence gathering, planning, and patient ambushes were involved before they even got to the fighting and looting part, especially for the pirates here in Essos.
There were not a lot of places in the world where pirates were welcomed so one of the most limiting factors for the pirates was a base where they could supplies. Thankfully the Stepstones were all under the control of forces friendly to pirates but only the most powerful pirates could station their fleet on Stepstones at all times and attack trade ships that came within their striking range which means that the other middling and smaller pirates had to leave the islands in search of targets in other places.
The Stepstone was like a massive tree from which the pirates spread out like branches into the nearby port cities' waters to prey on merchants' vessels. Some of them targeted the northern cities like Pentos, Myr, and Tyrosh while the others went downwards towards Volantis, Lys and the others.
Thankfully Essos wasn't a Kingdom or an Empire under a single ruler which meant that there were a lot of abandoned places and villages in between the cities where there was no government and no regular patrol so that they could set up temporary bases to supply themselves. But even after finding a place to set up, the work of a pirate is far from over, the next thing they need to do is to find targets to hit.
Most pirates always keep scouts in one or more of the nearby port cities so that they can scour the ports all day long searching for the fattest target that their fleet can take on. And when they find something like that, they immediately try to get the information, to their captains as quickly as they can, about when the ship is leaving and where.
If the Captain was happy with the target, they set sail immediately to the nearest uninhabited coast in the target ship's route and then dock there to wait for the target to arrive. A few sentry ships are sent to patrol at some distance from the coast so that they can always keep a lookout for all the passing ships. And since ships in this world aren't able to navigate if they don't sail while hugging the coast, it is usually possible to see all the passing ships even with the naked eye, though some ships sail far enough that they may not seem more than a dot, it is still more than enough to identify if it's their quarry or not.
The moment they identify their target, the sentries immediately raise the alarm, so that the pirates on the coast can board the ships as fast as they can.
After that, it is a race between them and their target if they set off from the coast fast enough. The pirates are usually able to catch up to their target more than eighty per cent of the time since trade ships are usually a lot heavier and slower than the more slender pirate ships which don't contain anything more than a few crates of food and a few barrels of booze. So the only place where they can mess up is if the sentries miss their target...
"M-Maybe they stopped to e-eat or they got l-lost at the sea—" This time the other pirate, Frank's nephew, tried to find a way for them to out of the situation but only made the problem worse as the Captain became even more mad.
"Hang these curses to trees and let 'em burn to death in the sun." The captain scoffed before going back towards his chair.
"No!!" "P-Please Captain!! Just give us one more chance!!"
"Captain Jack," And just as the rest of the crew were about to merrily carry their former friends off to hang them, the only man, without a beard on the coast, spoke, "It would be a waste to just kill them. Why don't you give them another chance, I am sure they won't make the same mistake again."
The man without a beard was the only one on the crew who could speak up and whom the Captain couldn't ignore easily. He was someone whom his father had sent to 'help' him learn. The crew only knew him as the Advisor and knew that he was the only one who wasn't intimidated by their captain's anger.
"Fine!" Jack grumbled before turning back towards the two pirates who had already been looted and almost stripped naked by the rest of the crew, "Frank, you'll go to Bravoos and try once again, and make sure that this time you get reliable information because if you don't then," the Captain suddenly smiled maliciously while looking at the nephew, "then yer lad here will be sold to the slavers to recover some of the cost of this trip."
From an economic point of view, every single trip for a pirate captain is a form of investment, and a costly one at that. With the cost of food, drink and the repairs of the ships being some of the unavoidable things, if they don't get good loot every few trips, they would go broke very soon.
"B-But—"
"Or I can sell the both of you right now and get my money even sooner," The captain cut off the pirate's pleas with that statement.
"No! I-I'll try my best and make sure that I get a good target this time, Captain," Frank said reluctantly.
"No! I want you to find that same fleet from last time," the Captain said with a gleam in his eyes, "I am sure that since we missed them, they probably completed their trip and made some good profit this time... which means that they are going to be an even fatter catch now..."
...
The one thing that the pirates were right about was that Jon's trip went without a single hiccup and was a mighty successful one.
In fact, by the time the pirates were expecting them between Pentos and Myr, they had already bypassed Tyrosh and were halfway through their trip and had even passed the Stepstones in the night without being spotted a single time. They didn't make any stops to trade in any of the ports before the Stepstones since the trade between cities such as Bravoos, Pentos, Myr, and Tyrosh was already flourishing very well.
Their only long stops were at Lys and Volantis, where they easily sold every single thing onboard into the waiting merchants' eager hands and on the way back they picked up as many local goods as they could to fill their ships.
When the fleet finally made their way back to Bravoos after a successful trip they were all welcomed with shocked exclamations from the crowd at the port.
"W-Why are they already back? It's been less than three weeks... Could it be that they failed the trip?"
"No! No! It can't be that. Look at all the goods that they are unloading from the ships. From the looks of it, it seems to have been a very successful trip."
"B-But that can't be right... You don't believe that they went all the way to Lys and Volantis in just three weeks, right? It usually takes at least three weeks just to reach there even if you only stop in the ports along the way for just a day."
"Maybe they didn't go all the way and just came back after going to Myr and Tyrosh..."
"Can't you see what the goods being unloaded are? Those intricate and beautiful tapestries and those wine barrels are definitely from the Lys and everyone knows that those crates filled with Sugar beets can only be found in Volantis. So they definitely went all the way..."
"But how did they complete the trip in less than half the time?"
"Maybe it was just a fluke... and the winds were just in their favour."
"But what if it isn't a fluke..."
Slowly but surely people's perception of the Company changed as they stopped believing that it was just a scam to trick them and even though not many believed in the company's boast about 100 per cent success, the shop still slowly started to fill with customers.
It was a completely different scene when Jon finally started to prepare for their second trip after resting for a week. For their first trip, they had to convince, coerce and even give discounts to the merchants to lure them in as customers, but for their second time, they didn't even have to do half as much. All the cargo space for the ships was filled shortly after they opened the slots.
While more than half of them were filled with returning customers who wanted to try their luck a second time, the rest were filled with apprehensive newcomers who wanted to try and take a gamble to see if they too could make the same profits as the others.
But what Jon didn't know was that his smooth and successful trip was having a very adverse effect on the life of a few pirates...
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