Okay, I'll bite. It's not about winning, I just love talking about old PCs!
Milo Yurinov (AKA "Healinov" AKA "Dimitrious Healinov")
A quick note before I go into the character - this was for a modification of Mystara my group played in for a while. It was set in a semi-post apocalyptic future of the setting. Our original characters were part of the setting's history. If any of them were still alive, they'd be in their nineties. Dimitrious Healinov was the character of another player that did not continue on. I built this character off of his, taking it in a slightly different direction.
The Traladaran people of Karameikos knew the name Healinov. In his youth, he was an adventurer, a man that walked out of his simple life on a wooded farm and into the vast world. He was a man that journeyed from one end of the continent to the other, fought alongside dragons, and helped stop a war between rival empires. But, more impressive to the people was the fact that, after all this was finished and his glory and fortune was set, he came back to those woods, settled among his people, and defended them from monster, beast, and prejudiced Thyatian. Long into the twilight of his life, he remained active in the region. You could always tell it was him by the pair of twin short swords he fought with, his family name and the name of his dead sister - taken by a vampire lord years ago - carved in the blade.
What people didn't know about Healinov, was that he had a ward. One day in the woods he found a small boy alone and scared. The boy told him his parents were dead. Healinov took pity on the child, who said his name was Milo, and cared for him like a father would. He taught him to track animals through the woods like one of their own kind would. He taught him which berries were safe and which were dangerous. He taught him to fight with short swords in the same manner that Healinov did.
Over the years, Milo grew strong and handsome into a youth seventeen years of age. Healinov would send him into the local towns to trade for goods the land could not give them. After one such trip, Milo returned to their hollow tree and cottage to find things oddly quiet. He called out for Healinov, but heard no response. Venturing in, Milo saw his mentor dead. Investigating, Milo found that age had not taken the old ranger. The corpse was withered, drained of its energy. It had been a vampire.
Milo knew the stories Healinov told about the vampire lord that took his sister. He suspected it was this same lord. He grieved openly for his mentor, the only father he could now remember. He burnt the body, knowing Healinov would want it done to prevent him from rising as one of the loathsome undead. Through the flames of that funeral pyre, Milo swore one day he would make the vampire lord pay.
No one knew about Milo Yurinov. But the name of Dimitrious Healinov was both respected and feared. Milo took up the studded leather and short swords of his mentor, fashioning himself gloves of tanned leather to cover his hands and a leather mask to obscure his face. He had Healinov's weapons, armor, and fighting style, and now he would claim Healinov's name.
Milo, calling himself 'Healinov,' went out into the woods. He became a specter, protecting the villages and taking the law into his own hands. With each act, the legend of his mentor grew, and people began to recognize Healinov as much by his sword as by his mask. The Queen of Karameikos sent her agents to find him, hoping a legendary hero such as himself would help her fight the civil war that was sweeping over Karameikos. Her brother, allied with a mysterious death knight, fought her for possession of the throne and was winning. In her service he went head-to-head with her brother on more than one occasion until he was forced to flee with the young princess and her bodyguards into exile when the capital fell.
Through it all, he continued to search for the whereabouts of the vampire lord, finally tracking him into the heart of Glantri. The Principalities had fallen to the undead nearly a decade before, but Milo traveled through the dark mists that covered it, searching for the vampire lord's estate. But finding it was only half the mission; he fought his way past the undead that guarded the estate, but the winding staircase to the tower home of the vampire, and to the door of its very resting place. There, he learned the horrible truth.
Dimitrious Healinov had slain the vampire lord when it took his sister. But he was foolish. He knew only folk lore about vampires. He never destroyed his sister's body. She rose as a creature of the night, and Healinov could not bring himself to kill her. She had come back to him that day in the woods, years later, to visit him before he died. She offered him the gift of undeath, but he refused. She never meant to kill him. It was an accident. She hadn't known about Milo. When the stories of Healinov's exploits continued to reach her ears, she thought he had risen as one of her kind.
Milo ripped the mask from his face, revealing the truth about 'Healinov.' He fought the vampire on her terms in her place of rest, finally winning when, without an escape left, she immolated in the rising sun.
No one ever saw 'Healinov' again. As to Milo's end, some say they heard tales of a youth that fought the undead in Glantri. Some say he helped the few pockets of the living there escape. It was dismissed as a myth, but the refugees in Darokin claim it is true. They carry a charm they swear wards off the dead. It is a tiny little mask of leather, tanned brown, with green lines across it at an angle like the claw marks of a beast.
Description
Milo stands five feet, nine inches tall. Like all Traladarans, he is of fair complexion with dark brown hair, almost black in appearance. He has a soft face with high cheekbones that almost has a feminine appearance to it, were it not for the constant growth of stubble on his chin. He wears his hair long - shoulder length - but leaves it untamed. He has an athletic build, one made not for feats of strength, but endurance.
When dressed for his role as 'Healinov,' Milo wears brown studded-leather armor that is covered in dark bit of metal that do not gleam in the day's light. The mask that protects his identity is made from the tanned hide of a cow, stretched over a wooden frame and boiled until it retained its shape. It has holes for the eyes, nostrils, and mouth, but otherwise obscures everything up to the top of his forehead. He has used pigments from the forest to paint a green design at an angle across the front of it, a design witnesses have likened to the claw marks of an untamed animal. In truth it is just camouflage, but Milo's strength is in nature, not art. Healinov's matching short swords are very old but well maintained, always cleaned and oiled before a fight. The hilt is wrapped in suede for comfort, and large Traladaran letters spell out 'Healinov' and 'Ikatarina' on opposite faces of each blade. He wears a reversible cloak - one side tan for the warm months, the other gray for the cold months - and a light green tunic and breeches with knee-high leather boots. His swords are worn on his belt, one on each hip, and Milo reaches across his body with both arms when drawing them. He wears the holy symbol of Halav loose around his neck even though he is not a cleric or particularly religious. His vendetta against vampires has caused him to embrace things they are weak against, regardless of his personal beliefs.
In combat, Milo fight's defensively, relying on tactics such as disarming or tripping a foe to gain the upper hand. He is fond of hit-and-run movements, using his speed to offset the smaller, piercing weapons he uses.
Key Event
During the first raid on the keep of the Baron that opposed the Queen, we made our way into the inner sanctum relying on stealth and a healthy does of psionics from the party psionicist. Since I was the closest thing to a thief we had, I (luckily) snuck into the room to eavesdrop on the Baron and his death knight ally. Now, none of us were the proper level to be fighting these people, which naturally means I failed my move silently attempt to sneak back out of the room. The rest of the party came to my aid, distracting the Baron and death knight long enough for me to get behind the wheeled desk in the room and run right at them with it. Next thing you know, I was riding a desk down the stairway with a very vexed death knight pressed against the front of it. It was a good thing I jumped off at the top of the stairs before its momentum carried it down and through the front door. It kept the death knight away long enough for us to escape and avoid that 10d6 fireball that would have reduced us all to ashes! After that, I took to lots of cinematic tactics; the DM enjoyed the change of pace and usually let me do anything that I had a reasonable chance of pulling off based on my non-weapon proficiency choices.