Crime doesn’t sleep in this city. Neither can I. Too many people have been hurt or lost or people they love to these vicious thugs and low-lives. I am no different. But unlike the city guard, I know where and how to hurt them back and make them lose just as much. Because I am one of them. I was raised within the circles of crime and violence that plague the city streets. But then I met Mari, and I realized that I would do anything for that woman. She let me into her life and began to teach me that there was more to life than what I knew. She taught me some of her skills – skills that I was able to marry to my own, turning them into something new and different. She pulled me out of the lifestyle that was fast corrupting me. She saved me. The bosses didn’t much like that, and they let me know.
I came back to our home one evening to find Mari’s throat cut open, our bed stained with her life’s blood, now turned a sickly brown in color. Her green eyes that once had so much light and life in them stared blankly up at the ceiling. Her lips, once warm and red were drained of color. Her face that never seemed to have anything other than a smile was twisted into an eternal mask of pain. I knew who was responsible, and I promised Mari that they would pay dearly for what they had done to her. I took the skills that I had developed over the last few years and went hunting.
It didn’t take long. I found them drinking in a small hole in the wall with the coin they had earned with her blood. I studied the scene. They were both deep in their cups, and the dagger that had torn out Mari’s throat was tucked into one of their belts. It still had some of her blood on it. I walked up and grabbed the dagger from the surprised killer. Then I buried it up to the hilt under his chin. As his life spilled out onto the table I incapacitated the second one and left the dagger on him. By the time the city guard showed up, I was long gone. The killer’s accomplice is still sitting in a jail cell for the murder of his mate. I hope he never sees the sun again.
As for me… well, you know the rest of the story. I knew I couldn’t leave it at that. Taking that vengeance felt good. So I invented the identity of the Red Alley Avenger, letting criminals know that the streets would be painted with their blood for what they had so long done to the city. And if I might brag a little bit, I have been doing very… very well.
I was recently poking around some of the class options that I often look at but never really thing about putting onto virtual paper, as I am wont to do in my spare time. Usually, nothing much comes of the idea, but this time I hit what I think could be a very fun character to bring to a city based campaign – Triskan, or “The Red Alley Avenger” as he is more commonly known to the people of the city. Entertainer by day, vigilante by night.
I honestly had a hard time in choosing between the Criminal background and the Haunted One from Curse of Strahd, and you could pretty easily swap one out for the other if you so choose, depending on how brooding you want to make the character. The Mobile feat was chosen with the bard’s blade flourish ability in mind, giving this character a walking speed of 50 ft. in a round as long as he makes a melee weapon attack in the round. But I had also entertained the idea of taking Defensive Flourish to help keep his AC up against incoming attacks. As far as advancement is concerned, there’s no reason that he couldn’t continue on the bardic path. There are any number of interesting spells on that list that would fit the them of the character. However, I could also recommend multiclassing into rogue and picking up the Swashbuckler archtype from Xanathar’s Guide to Everything to capitalize on your Charisma score already being higher than average, as well as giving you better damage potential with sneak attack dice. Cunning action also allows you to get more out of the Mobile feat’s interaction with the Dash action.
This character was built with the D&D Beyond Character Builder
https://www.dndbeyond.com/profile/darkcyril/characters/5578232