Horatio "The Commodore" Flashman

The truth of my origins is not something share all that often, but I suppose there is no harm in this instance. I mean look at you, who’s going to believe you?!
To the masses out there, I am Commodore Horatio Flashman, late Everwinter Sea Trading Company. I make a humble living as broker to the most respected of Merchants and Traders; I’ll ship your valuables on only the safest of ships for a very reasonable price, have the voyage insured through the Counting Houses of Verus, I’ll even buy you a well lubricated lunch to show my appreciation of your custom and assure you that I can always be found at the Port Trading House if need. I can see you have not quite caught on yet so let me break it down in a way that you can understand, the goods are not going to make it to their destination, but by that time I’ll be long gone and your gold with me. In truth, I was born Edward Meretricus in the Imperial colony of New Calderon , that’s in Altharad if you weren’t aware. My mother was an Elven whore, my father one of those Imperial cunts who settled on Elven lands after the conquest. Of course my mother couldn’t bring herself to love a half-breed so I was dropped off that the local orphanage where I lived for the first decade of my life. Shortly before my eleventh birthday, the bosun of a visiting cargo ship, the Olivia, showed up in search of a cabin boy, being among the older residences and a half-breed with little chance of adoption anyway, the Matron convinced the drizzled sailor that I was the obvious choice. I made no protest, anything to get out of that hell hole. Life at sea was tough for a boy not even in his teens, my pointed ears and bastard surname instantly gave away my heritage. I grew up tough and cunning, I got by through conning the dim-witted sailors out of food and coin, while my natural charm kept me on the right side of the Officers. Over the years I grew up to become an able sailor and a gifted swordsman (piracy across the Sea of Tiavyrm meant I got plenty of practice), but I will admit I also developed a great passion for inflicting pain on those who wrong me, and when you’re passionate about something you do tend to get rather good at it! By the time I was eighteen, my natural ability was finally noticed by the vessel’s First Mate, who took it upon himself to school me in the arts of Navigation and Vessel command. First Mate Hartree was a fat, drunken fool when we were ashore, but at sea he climbed the rigging with the speed of a first class athlete and his seamanship was unmatched. I will admit I liked the oaf, something of a father figure I suppose, if you buy into that shit. It wasn’t long before I surpassed the best of those stuck up brats that made up the Olivia’s class of Midshipmen and at aged 22 I was sent to the New Calderon Naval Academy to sit my Mates exams, it was finally a chance to escape my ragged heritage and build a decent life as ship’s officer in the Imperial Merchant Fleet. I sat in front of the board of examining Captains and for two hours they asked my every possible question on Navigation, Seamanship, and Imperial Maritime Law. I flew through that exam, answering every question confidently and correctly, after a brief recess I was informed by the head of the board that I had not met the required standard. I was angry, I’m man enough to admit that, I am still half human after all! I pressed the Captain, demanding the cretin tell me exactly what it was I had failed on, eventually he broke and angrily told me that there was no way a half-breed son of a whore would ever sail as an Officer in the Imperial Merchant Fleet. The good Captain was found in an alley later that night, unconscious with a broken jaw and a few cracked ribs, nothing to do with me of course! And there’s no proof at all that the hat, coat, and spyglass that found themselves into my possession ever belonged to him!
I never returned to the Olivia, I had already wasted too many years on the futile path. I stowed away on a leaving cargo ship, I didn’t care where she was headed. I moved from port to port and made a lot of friends along the way, people who helped me hone my less honourable talents. I took the name “Horatio Flashman”, and with the aid of a stolen badge of rank and forged Captain’s papers, quickly gained the trust local Merchants and Shipmasters. I ran three brilliantly simple criminal ventures. Firstly, I would “assist” wealthy Merchants in shipping their valuables and coin across the Sea of Tiavyrm for a discounted fee, I simply pocket the coin, fence the goods, and disappear once the standard sailing time has passed. Secondly, if I got wind of something of particular value being shipped, I would tip off my pirate contacts with the name of the ship and the passage she was taking. Once the ship has been successfully looted, I take my share. And lastly, I had a good run smuggling illegal goods by paying off Captains to use their free cargo space, unfortunately it was this enterprise that has landed me in my current, less than ideal, situation.
I had made a sizable sum of coin over the last four years and I will admit I had started to believe I was never going to get caught, the Ministry of Impartiality aren’t exactly recruiting from the cream of the crop! On a visit to Altharad, my maternal uncle reached out to me with a proposition, he had got his hands on a case of magically infused Elven spears. Of course I knew the risk, but the Empire’s heavy regulation of magical items, particularly of Elven origin, meant I could charge my buyers a fortune. The kind of fortune I could buy a ship with, possibly a fleet!
I knew just the Captain for the job, a slimy half orc as crooked as he was ugly. Even a small share of the final pay-out was enough for him to eagerly agree and I was sure I could trust his discretion. Unfortunately, I didn’t account for him opening his grotesque maw in the Officer’s mess within earshot of a rather disgruntled Chief Cook. No sooner had we reached the Duskember Coast than Agents from the Ministry of Impartiality were coming aboard with warrants for our arrest. The Captain was arrested immediately, but I slipped the net and led those fools on a merry chase up the coast for almost a month! I made it as far as Tethoris and had a berth secured on an incoming ship, I was THIS close! But the bastards' had a constable watching the Seaman’s Union and I was made. The trial was a joke; no jury, fabricated witnesses, and a judge who’d clearly grown up listening to exaggerated tails from the Altharadi/Imperial War. They gave me thirty years hard labour on the colonies, bold of them to assume they can hold me that long!

Basic Information:
Age - 26
Born - New Calderon
Race - Half Elf/Human