Cursed Traveling Merchant

You’ve spent your life navigating the world. You studied the traditions, needs, and exports of cultures from across the land giving yourself a broad view of the world. You have worked on a merchant caravan, a ship, and even the occasional stall. Everything was going so well! You had a life of luxury, love, and comfort when you suddenly lost it all. Perhaps you angered a witch, devil, fey, or divine being. Whatever the case, you have a curse set upon you. Whether it be a rule or condition, or a form of blight. Possibly a brand? Whatever is may be, there’s a reason for it. And it causes thines own suffering. 

Your desperation has driven you to the career of adventurer. You don’t seek out dark dungeons and their monstrous inhabitants for excitement and glory; you do it because every other path is closed to you. But you have risen high on fortune’s wheel once before, and with luck and fortitude, you could do so again.

Feat: Pick a cursed Feat.

Skill Proficiencies: Choose two from among Insight, Arcana , Religion, Acrobatics, or Deception.

Tool Proficiencies: One type of artisan’s tools or musical instrument of your choice. One type of vehicle proficiency.

Languages: Choose one exotic language (Abyssal, Celestial, Deep Speech, Draconic, Infernal, Primordial, Sylvan, or Undercommon) Choose 1 other Language

Equipment: 1 uncommon ring of your choice, a set of traveler’s clothes, a half-empty bottle, and a pouch containing 13 gp

 

Suggested Characteristics

Years on the road — and under a curse — have hardened your wit and warped your worldview. You’ve bargained with saints, swindlers, spirits, and sometimes all three in the same day. Whether you face the world with humor, paranoia, or grim resolve, every trade and every scar is just another entry in your cosmic ledger.

d10	Personality Trait
1	I treat every bargain like it might be my last — I’ll haggle with fate itself if it means breaking even.
2	I stay unnervingly cheerful about my curse; optimism is cheaper than despair, and it sells better, too.
3	I don’t run from evil. Evil learns to cross the street when it sees me coming.
4	I’ve seen true misfortune, so when others complain, I just smile and nod — they’ve never bartered with doom.
5	A tavern brawl is just an aggressive form of negotiation — and a fine way to make local connections.
6	I trust neither the divine nor the damned; every blessing I’ve ever received came with an interest rate.
7	I collect charms, trinkets, and prayers from every faith I meet. One of them has to work eventually… right?
8	I can’t help but flinch around beings that share the same origin as my curse. Some debts are better left unpaid.
9	I never forget a face, a debt, or a deal. Those who cheat me once tend to regret it twice.
10	I see hidden meaning in everything — a sale gone wrong, a broken wheel, even spilled wine. It’s all part of the pattern… I just haven’t solved it yet.

d8	Ideal
1	Generosity. My misfortune taught me compassion — I give freely to those in need, even when I can’t afford to. (Good)
2	Retribution. Whatever cursed me will pay its due. I’ll drag the source of my suffering into the light, one deal at a time. (Chaotic)
3	Greed. Every deal, every haul, every coin — it’s not about wealth, it’s about proving I can take what fate tried to deny me. (Evil)
4	Freedom. No god, curse, or contract owns me. I trade where I will, and I answer to no one. (Chaotic)
5	Community. Civilization is just a network of bargains. I honor mine, and expect others to do the same. (Lawful)
6	Triumph. Every victory is a small rebellion against my curse — a reminder that I’m still the master of my own trade. (Good)
7	Defiance. My curse will not define me. If it cannot be broken, then it will learn to live with me. (Any)
8	Aspiration. I work tirelessly to become the best merchant on any road — cursed or not, my name will be remembered. (Any)

d8	Bond
1	My first caravan was my true family. I still carry the ledger of every name lost along that road.
2	I was cheated out of my fair share once; I swore then I would collect what was taken—by coin or by blade.
3	Bandits ambushed my traveling party and slaughtered everyone I trusted. I survived, but I remember every face.
4	The curse claimed the one person who ever loved me. I’ll see the world burn before I let it take anyone else.
5	I took the place of someone meant to bear this curse. Guilt walks next to me; one day I will earn my redemption.
6	This curse drove my lover (or family) away. I will do whatever it takes to bring them home, even if it breaks me.
7	My mentor or guild forged me into a trader; I owe them everything. I will repay that debt with loyalty, blood, or gold.
8	I defaulted on a loan from shady men and was driven from towns as bad luck. Either I repay my debt—or I confront those who made it.

d8	Flaw
1	The Curse’s Scapegoat. I blame the curse for my misfortunes—even when they’re clearly my fault. It’s easier than admitting I messed up.
2	Sticky Fingers. I can’t help but pocket shiny things. Old habits die harder than debts.
3	Bottle’s Grip. Once I start drinking, I don’t stop until the bottle’s as empty as my coin purse.
4	Passing the Burden. Part of me wonders what it’d feel like to hand my curse to someone else. I tell myself I’d never do it… but I’ve thought about it.
5	Pride’s Fall. I’d rather ruin a deal than lose face. My ego’s more expensive than any contract I’ve signed.
6	Haunted Sleeper. Nightmares and panic attacks stalk me like creditors. Some nights, I don’t sleep at all.
7	Paranoid Tradesman. I assume everyone’s trying to cheat me—because most of them are. The few who aren’t usually pay for my suspicion anyway.
8	Jealous Eye. I can’t stand those who live free of debt, curses, or consequence. Their happiness feels like theft.

Contacts

Traveling Merchants are cultured, well-traveled, and worldly. Every deal leaves an impression — some good, some burned beyond repair. You’ve earned friends who still trade with you despite your curse, and enemies who cross the street when they see you coming.

Choose two or three Contacts who still offer you help, and two or three Former Associates who refuse to deal with you. Together, they form the trail of debts, loyalties, and grudges that define your cursed career.

Once per long rest, you may call in a minor favor from a contact — such as safe passage, a small loan (up to 100 gp), information, or temporary storage. Each use deepens your debt counter with that contact; push too far, and they’ll avoid you or demand repayment.

You may also call in one major favor — a dangerous or costly request, like forged papers or smuggled passage. When you do, that connection ends forever. Whether by betrayal, fear, or fate, they vanish from your ledger for good.

d12	Contact
1	Caravan Master. A veteran trader who still remembers your reliability on the road. You gain advantage on checks to join or organize caravans, and travel costs are reduced by 25% when moving with them.
2	Wagonsmith. A skilled craftsman who maintains your gear out of respect (or pity). Vehicle repairs or modifications cost half price, and travel mishaps involving wagons or carts are easier to fix (DM may grant advantage on related checks).
3	Beast Handler. Knows every trick to calm a stubborn camel, ox, or owlbear. Stable fees are waived, and you gain advantage on Animal Handling checks when working with pack or draft animals.
4	Arcanist Merchant. A traveling spell trader who dabbles in enchantments. Gain 10% discount on scrolls, potions, or minor magical trinkets, and you can sometimes identify unknown items without cost if they owe you a favor.
5	Security Captain. Once your hired muscle, now an ally who still calls you “boss.” Gain advantage on Persuasion checks when hiring guards or mercenaries, and they’ll offer 15% lower rates for protection contracts.
6	Clandestine Acquisitions Specialist. A fancy term for your favorite smuggler. You gain access to illicit goods (DM’s discretion) and advantage on checks to source contraband or forbidden wares.
7	Thieves’ Guild Fence. An underworld broker who buys what others won’t. Gain 10% higher resale value for stolen or “untraceable” items and advantage on Deception checks involving black-market deals.
8	Black Market Leader. A crime lord who admires your nerve and discretion. You can request illegal passage or forged documents at half the normal price once per month, no questions asked.
9	Banker or Loan Agent. They trust your ledgers, not your luck. You may secure small loans (up to 100 gp) without collateral and gain advantage on Persuasion checks to renegotiate debts.
10	Appraiser. An old friend who still respects your eye for value. Gain advantage on Investigation checks to appraise or authenticate valuable items, and legitimate buyers treat your valuations as credible.
11	Skyship Captain. A daring trader of the clouds who enjoys your company and your whiskey. Gain discounted sky passage (25%), and you may ride along free once per year if the captain owes you a favor.
12	Real Estate Broker. A professional who still believes in your prospects. You can secure temporary storage or lodging in most major cities, often at half cost, thanks to their network of trusted clients.

d12	Non-contact
1	Caravan Master. Once your road companion, now wary of your “bad luck.” Caravan groups charge you double rates or deny passage unless you prove your worth anew.
2	Wagonsmith. Grew tired of your unpaid repairs and strange incidents. You pay 50% more for vehicle parts or repairs, and some workshops refuse your business outright.
3	Beast Handler. One too many animals died under your care. Disadvantage on Animal Handling checks with pack or draft animals until you earn a new handler’s trust.
4	Arcanist Merchant. Claims your curse “contaminated” their wares. Magic items cost 20% more, and identifying enchanted goods takes twice as long without assistance.
5	Security Captain. Lost good people guarding your caravan. You must pay full advance wages up front when hiring mercenaries, and they treat you with suspicion.
6	Clandestine Acquisitions Specialist. You were too loud, or too honest. You lose access to black-market goods in one major city, and the underworld has placed you on a quiet hitlist.
7	Thieves’ Guild Fence. Claims you sold them counterfeit goods. You get only 50% resale value for illicit items and may be harassed by guild agents in larger towns.
8	Black Market Leader. You called in a favor one too many times. You are blacklisted from local smuggling routes, and anyone caught helping you risks reprisal.
9	Banker or Loan Agent. Your name is on a parchment of shame. You can’t secure loans in legitimate institutions and may face collection attempts or bounty hunters.
10	Appraiser. You “forgot” to return a borrowed gemstone. Appraisers and auction houses apply a 25% fee up front, and rumor paints you as a con artist.
11	Skyship Captain. Your curse nearly downed their vessel. You are barred from sky passage with most reputable captains; smugglers might still take you—for a steep premium.
12	Real Estate Broker. You vanished with valuables left in their care. You are denied access to safehouses, storage, or property networks, and urban landlords may charge triple rent if they recognize you.