Cayleb Ahrmak seems like he was destined for the sea, whether he liked it or not. Born on the Isle of Medeogotli, his parents were Taldan expatriates who, along with the rest of their extended family, smuggled coffee aboard the Roaring Lion. Moving coffee to the mainland and undercutting their mwangi business rivals. Cayleb, like the rest of his cousins, was always taken out to sea with the family to teach him their trade. On their relatively frequent stops in Ilazgamorti, Cayleb was taught to be simultaneously suspicious and courteous to anyone you didnt know, for who knows who among the citzens of the isle were members of the infamous red mantis?
When he was 14, his parents lost their ship in a particularly fierce hurricane. While everyone was able to make it safely ashore, the real harm was in losing their valuable cargo, for their partners, who funded half their stock, were not the kind of people you would care to owe money too. Upon hearing of the loss of their money, they immediately sent bounty hunters out searching for the family Ahrmak, eventually catching them up to them near westcrown. The older members of the family, including his parents Doritian and Xemne were sold into slavery, While Cayleb and his cousins were shackled with the relatively minor punishment of indentured servitude.
Cayleb was picked up as a very cheap swabbie aboard the pirate vessel Leviathan’s Wake. He never really had a taste for the pirate life, but aboard the Leviathan’s Wake wasn’t the place to learn a respectable trade. He rather quickly gained a name for himself, both for knowing the workings of a ship better than many lifelong old salts, and for being an insubordinate pain in the ass. This arrangement wasn’t fated to last, since, as the old adage goes, there is always a bigger fish, leviathan or not.
The Last Word, the flagship of the chelish navy, boarded the Leviathan after a grueling 2 day chase, and upon the capture, showed very little quarter, leaving only young cayleb and a priest of Gozreh alive, one in the hopes of rehabilitaion, and the other for fear of angering the sea himself. Surprisingly enough, Cayleb finally found something he liked less than hardships of the pirate life, and that was the discipline of the navy, for at least the pirates were honest about it. The shiftless lad quickly learned the taste of the lash, for insolence. This only taught him new, more subtle ways to be insubordinate, and the more important lesson of picking your battles, and always having the advantage. To this end, he became a quick study of people, and just how far in general he could push them. After about a year of this hell, he was able to slip the tight leash the chelish officers kept on him, slipping quietly into the night on a routine port stop in the chelish city of Corentyn.
In his new home, he actually did quite well for himself. He picked up a job with the local fishermen, going out everyday, coming back, and peddling the day’s fresh catch (he even learned how to cook). The crew he worked with was friendly, and no one would dream of using the lash. He was able to impress his boss, and was even given stewardship over his own boat. It was a good couple of years, until Cayleb royally screwed up. He had caught the eye of the fleet owner’s daughter, and like any red blooded male, took her up on her offers. One night, her extremely conservative father was having a nightcap after a bad night of sleep, and saw Cayleb, clothes and hair askew, coming from the direction of his little princess’s room. As much as he liked the boy, he was not about to let some taldan punk ruin his daughter’s future. so he had him quietly drugged, and put aboard a slave ship on its way to the shackles.
Once again finding himself aboard a strange ship, Cayleb didnt waste a bit of time escaping. Convincing some of his fellow capturees, as soon as the ship put into port, they immediately overpowered their guards, and escaped into the dark streets of Port Peril.
Deciding to celebrate his new found freedom, Cayleb stopped in the Formidably Maid. Having learned his lesson, he watched his drinks, watched the door, let no one behind him, and entertained no one at his table, spending his meager coin on some ale. On his way out, he was followed by the press crew, who coshed him, and dragged him to the harbor to fill out the ranks of the Wormwood. That had to be some sort of record, not even a day between escaping one ship and getting pressed on another.
Cayleb never really sought a captain’s power, because he didn’t really want a captains problems. All he is really looking for in life is a little adventure and independence. After serving under Captain Pari, though, he has learned there is definitely worse fates than being in charge. After becoming captain, he decided to abolish the practices Pari started that he couldn’t abide, such as slavery. He keeps to the pirate life mostly as the best means to keep his freedom. Despite his skill at arms, he dislikes fighting, usually just intimidating a ship into letting him loot it, and then sailing away. Being forced into combat tends to put him on edge, putting him in a markedly worse mood (he is normally pretty happy go lucky). Due to a competitive streak, that doesn’t apply to other pirates, generally, and slavers can count themselves dead. He prides himself on being able to out-sail, out-fight, and out-perform anyone else who flies the red flag of piracy. He values competence, and likes putting the right person to the right job. He likes his ship being well run (the one artifact from his time with the navy), and will occasionally drill his crew in how to handle a situation. Knowing he works his sailors harder than most would, he lets them unwind in anyway they choose, and has few bordering on no rules concerning times they aren’t on watch, stepping in only when it threatens the ship. Being a young, fit male, he flirts with pretty much every cute girl he sees, in the hopes of a friendly tumble. He distrusts alcohol, seeing as how people seem to try to keep drugging him with it, instead drinking coffee that he prepares himself, a habit he remembers from his parents.