Desperation Island: 21st Century Pirates in the Caribbean

By Keith A Hamilton

From the author of Nine Bear Lodge comes another novel. Modern-day pirates build a fleet and a crew, and terrorize small boat operators throughout the central Caribbean islands. When they come to the notice of national law enforcement teams, they face the wrath of modern technology as well as facing the revenge of one of their victims, a Russian mafia gang.

• Language: English
• Publisher: Tellwell Talent
• Release date: Sep 29, 2023
• ISBN: 9780228894643

Keith A Hamilton

Since the early 1990s, Keith A. Hamilton has lived and worked in small remote Indigenous communities throughout Northern and Western Canada. He has made Bella Coola his home since 2016. He and his wife and their dog enjoy the beauty and serenity of the Central Coast region.

Book preview

ONE

It didn’t look like much from the air. A small island surrounded by sea. The island seemed like it shouldn’t be there. There were no other islands nearby. No hints at which direction lay the nearest settlement. This was truly a remote spot.

Approximately one mile long by half a mile at its widest point, the land rose slowly out of the sea on the leeward side. Without any sort of reef, there was a shingle beach and a smallish inlet, suitable only to protect the smallest of craft from the wind and tides. A small creek gave evidence of fresh water, which came from a spring on the windward side.

The land rose slightly as you moved windward, following the creek. In the low lands off the beach there was very little vegetation: scrub grasses, sedge, some wind-borne grass seeds sprouting in clumps where there was some shelter from the sea breeze. Alongside the creek some dense brush, covered in aromatic tropical flowers, grew to about head-height. The constant wind kept the brush bent over and moving constantly, swaying like a cobra hypnotized by a snake charmer.

The highest point on the island stood perhaps 150 feet above the surf, constantly crashing below. The rock was ancient granite, weathered smooth by wave and wind action. On the cliff face the nests of various sea birds clung precariously. The top of the escarpment was worn smooth, like a billiard ball, with a top surface nearly flat.

From the lee side of the rock, a crack emerged from the underbrush, and a pool of water bubbled up to the surface of the small hidden spring, tumbled over the edge of the rock, and began its short journey as the unnamed creek, ending in the surf in the middle of the small inlet.

No one lived here, that was obvious; maybe nobody ever had. No one even knew this place existed. The mariners’ charts didn’t show this place. They were far from the usual sailing lanes. A quiet, secluded hole in the ocean. It was exactly what he was looking for. As far as he could tell, none of the myriad Caribbean nations claimed this forlorn rock as their territory. That was perfect for him. He would claim it himself. So like an explorer from the fifteenth century, he dismounted from his small coastal cruiser, anchored in the inlet close to shore, waded to the beach, climbed onto the shingle, and walked a few feet in shore. He reached a likely spot, pulled out a small square of painted canvas, placed it on the ground, and held it in place with loose shingle stones. The flag had been his own design, sort of a hybrid combination of a skull and cross bones and the Cross of St George. An homage to his English ancestry, if you will. He claimed he was a direct descendant of Sir Francis Drake, who was first a privateer in these waters, fighting the Spanish for a piece of their treasure ship fleet, then later the Admiral of the English fleet that beat back the Spanish Armada. His branch of the family missed most of the financial legacy, but he felt a close connection to his kin nevertheless.

I claim this island in the name of my many times great-grandfather, Sir Francis Drake. The life of a pirate in Drake’s day could be called desperate. In between fighting for their captures, the pirate crews would live in remote locations like this one as pariahs without any local support. The men who chased for prizes had to win or die. Their lives weren’t glamorous like in the movies. Desperate times lead to desperate measures. To honour those brave men who have gone before, I name this island Desperation Island. Thus begins the reign of King Ronald Drake I, ruler and sole possessor of this place. Long may he reign.

Ronald may have been his name, but Drake was an affectation. His legal surname was actually Johnson. He found out in high school, while doing a genealogy assignment no less, about his ancestral line. There was some doubt in the official record, and his teacher didn’t accept the result as verified. But he was convinced. He recalled he became a bit of a minor celebrity in school that year. His was the only family tree with famous roots (at least as he loudly proclaimed). The fact of his being a Black member of that White family line explained both the lack of financial wealth, as well, he supposed, as his growing up not on an estate in England but on the streets in Antigua.

But he was going to change all that. He made a study of all that could be known of his erstwhile famous ancestor. Like Drake before him, he planned to make his fortune the old-fashioned way, as a privateer. He had no illusions about gold from the Spanish Main, but he knew there was plunder, and he was going to have it. He had no illusions about morality or right and wrong. He would have been diagnosed as a sociopath had he ever had an interview with a psychologist. He felt there was one right, and that was what was right for him. Nothing and nobody else mattered.

The first step was now done. He had his hideout. Now to build his base and recruit his gang. He had to be careful not to draw attention. He would buy supplies from many different sources, trying not to get too much from one place. He could only take small loads at a time on his boat. He didn’t want to answer awkward questions about where he was going with building materials, so he always had a cover story ready. His uncle or his cousin or some other unnamed relative wanted his help on a DIY project.

He had been working a series of menial jobs most of his life, just trying to get by. He was lucky he now had a job as a custodian in his old high school. The job came with various employment benefits thanks to the union. He thought of his pension funds as his privateers’ fund. Now he had a reason to use it. He made his withdrawals in smallish pieces—enough to buy the latest shipment of supplies and materials and tools. He had a cover story there too. He told his banker he was supporting a woman from another island. This was common enough that the banker didn’t question it. He wasn’t responsible for his client’s future pension, after all.

His work shift was seven days on and four days off, leaving him time on his breaks to collect his materials and make his way to Desperation Island. His first recruit was a co-worker, Jemmy. Jemmy was a man of considerable size and great muscular build. As a privateer he will be very intimidating, thought Ronald, and as a builder’s assistant even better. He was sworn to secrecy and then sworn in as the first member of Cap’n Drake’s crew—his First Mate.

For several weeks, together they slowly built first a small dock, then a small shelter in the middle of the island, near the creek. It was primitive, but it was enough to keep the rain out and provide shelter from the constant sea breeze. In between building assignments, Ronald spent time teaching his First Mate his duties. Most Antiguans had a knowledge of the sea, but Jemmy was not like most. He had never been off the island, not even to go fishing. The intricacies of navigation were beyond him, but with repetition he began to understand the ways of boat handling. He may never understand currents or tides, but he was becoming adept at pointing the boat in the direction you wanted and keeping it on track to its destination.

Next, the hard part, thought Ronald. He needed to secure some weapons. He wasn’t a killer, he thought, and didn’t intend to use the weapons, but he knew if you didn’t show the weapons you’d not convince anyone to hove to and be boarded. It wasn’t that he was against killing. After all, pirates have always been known to kill their victims, and he was a pirate. But his self image was as a pirate king, and such people always had henchmen to do their bidding. He thought he could reap the rewards without having to do the dirty work himself. So not only was he going to need weapons but also someone on the crew who could use them. Antigua, being a British colony, had British laws, including weapons control. Ronald, and indeed Jemmy, had never owned or for that matter used a gun, either a long gun or personal protection piece. He was going to need to recruit another crewman.

Ronald started spending his spare time at the docks. Since everything on the island came in by boat, it made sense he would eventually find someone at the docks who knew how he could get his guns. This was the dangerous part. Jemmy had been a co-worker, one who had heard of Ronald’s connection with Francis Drake and had heard the stories of some day becoming a privateer himself. Jemmy was, if Ronald was honest, a bit simple-minded. Simple-minded people often made the best friends, he thought, and they were very loyal. Jemmy was an excellent, hard worker who took direction very well. He wasn’t prone to thinking about things much. He accepted what he was told by Ronald almost without question. Like Ronald, the question of morality was not something he thought about. He’d been taken advantage of for most of his life, until he became large enough to physically stand up for himself. He believed, and Ronald supported him in this, that you look out for number one, because nobody else will.

So far what they were doing didn’t cross any lines. Nobody would go to jail for building a private clubhouse. But the next member of the crew needed to be their triggerman. This person would need to be ruthless, not hesitant to use violence to achieve his objectives. This guy wouldn’t be interested in fantasy stories about pirates. He was looking for a criminal. Someone who would look forward to robbing people on the high seas. Finding this person without calling attention to himself among the police informants, and then convincing him to join the crew, took several weeks of careful surveillance of the docks, and it cost Ronald a fair amount of coin at the local pubs.

Farley was Jamaican, his dreds falling nearly all the way to his waist. He was a drifter, and his