Trouble

New D&D character! He's a Tiefling named Trouble.

Trouble was born to a human couple, nobles by the names of Errol and Malin Riverguard. His Father Errol, horrified and disgusted by the Tiefling child, insisted that they kill him on the spot. His Mother however, took pity on the infant and discreetly delivered him to an orphanage in town in the dead of night.

His time at the orphanage was miserable. He was treated with cruelty due to his race, outcast and ostracized both by the other children and the caretakers. There, he was only referred to as “boy” no one had bothered to give him a proper name.

His only comfort, was the occasional letter from his mother. In these letters, she would lie, saying she was poor and couldn’t afford to have a child. She would make up stories of how she was trying to get her life together, so she could come back for him and they would live as a happy family. None of this was true however, and though she felt guilty enough to send the letters, she never intended to give the child a home. The letters suddenly stopped after his 12th birthday. Unbeknownst to him, his mother Malin would continue to keep tabs on him throughout his life.

At the age of 18 he was cast aside and expected to fend for himself. He panhandled, and sometimes stole to survive. He was often treated poorly when he begged. On one occasion, he had asked the wrong noble, and received a horrible beating as a result.

After this, he was determined to teach himself to fight. He routinely got in trouble starting brawls with anyone who treated other beggars poorly, or whoever he decided deserved it. He was even jailed for a few years for attempted murder after nearly beating a man to death after he had watch him give a woman a black eye.

Eventually, he had caught the attention of a group of thugs, looking to have him join them. This is how he earned his name. A much older, muscular dwarven woman, with an impressive red beard had approached him. Her first words to him were “You look like trouble. I like that.” She introduced herself as Naleen, a former private investigator who’s reputation and career was ruined. She offered him a way to earn more money than petty thievery and panhandling. He accepted her offer, and together with the others, they were unstoppable. They stole only from those who were well off, had personally wronged the group, or just simply “deserved it.” They refrained from ever killing innocents. However, this didn’t stop the group from occasionally dishing out some serious damage. But they were always careful to never take a beating too far.

The group consisted of a total of 6 people. Nimble River, a Tabaxi rogue, Hazir, a Half Orc barbarian, Vierna, a Drow warlock, Valkira, a Dragonborn paladin, and of course Naleen and Trouble, both fighters. Over the years, he grew close with all of them, considering the crew his family. Especially Naleen, who he saw as a maternal figure.

One day, Naleen approached the group with a plan for a new heist. They were to target human nobles, who were none other than Errol and Malin Riverguard, Trouble’s birth parents. After Naleen had learned the truth about Trouble’s parents through some investigation, she decided they ought to pay his folks a visit.

Trouble was outraged to learn of his mother’s lies. He felt they had robbed him of a good life. They were far more than capable of providing for him. He burned the letters he had held on to and cherished, vowing to get his revenge on his parents. Though he didn’t wish them dead, he still wanted them to pay, literally.

The night of the heist, however, did not go as planned. The guards were on high alert and prepared for a fight. They were quickly spotted, and while the fight was difficult, they persevered. While they were able to incapacitate the guards, they took a beating, and had woken the rest of the household.
Most of the group was injured, and wanted to take what they could and leave as soon as possible. But Trouble insisted that they keep going.

Naleen was caught off guard while the group was distracted stuffing their pocket and exploring the manor further. Errol had seen just her, and had managed to sneak up behind her, stabbing her repeatedly in the back. She yelped in pain and fell to the floor like a bag of bricks. Trouble rushed over, and as the others followed suit Errol realized he was outnumbered. He made his hasty retreat.

Trouble fell to the floor at Naleen’s body, cursing, sobbing like he’d never in his life. He took Naleen’s silver necklace as a memento, clasping is around his neck. They had little time to mourn however, quickly making their escape before city guards could come to apprehend them.

Without Naleen to lead them, the group was lost, and eventually disbanded. Trouble felt more without purpose than he’d felt since meeting Naleen.

Now more than anything, Trouble wanted revenge. He didn’t just want to put a dent in his father’s fortune, he wanted his head.

Now in his late 20’s, Trouble finds himself always looking for a new crew. Though he wishes his had never went their separate ways. He’s constantly wondering what became of his friends, and hopes to at least run into them one day on his travels.