You’re an agent of the Shadowmasters of Telflamm, a thieves’ guild that is strongly linked to the worship of Mask. The Shadowmasters rule Telflamm in secret through their web of spies and thieves, rivaling the influence and power of the local nobility and clergy. You are, or at least were, just one tendril of the sprawling shadow that the Shadowmasters cast over the city. You might have even briefly escaped the guild and its machinations, but, willingly or not, everywhere you go, you further the seedy agenda of the guild’s elite, the shadowlords.
- Skill Proficiencies: stealth, deception
- Tool Proficiencies: One of your choice
- Languages: One of your choice
- Equipment: A crowbar, a set of dark common clothes including a hood, and a pouch containing 20 gp
There are many kinds of criminals, and within a thieves’ guild or similar criminal organization, individual members have particular specialties. Even criminals who operate outside of such organizations have strong preferences for certain kinds of crimes over others. Choose the role you played in your criminal life, or roll on the table below.
| d8 | Criminal Specialty |
|---|---|
| 1 | Blackmailer |
| 2 | Burglar |
| 3 | Enforcer |
| 4 | Fence |
| 5 | Highway robber |
| 6 | Hired killer |
| 7 | Pickpocket |
| 8 | Smuggler |
The Shadowmasters are adept at gathering information and have eyes and ears everywhere. In every town, city, or other settlement, you know of another Shadowmaster Agent who you can rely on to fill you in on information about the settlement’s main features, figures, locations, and organizations, as well as other underworld activity in that settlement and you have access to the shadow network, which allows you to communicate with other members of the order over long distances. If you write a letter in a special arcane ink, address it to a member of the Shadowmasters, and cast it into a fire, the letter will burn to cinders and materialize whole again on the person of the agent you addressed it to.
Spell List
If you are a spellcaster, the spells on the Shadowmaster’s Agent Spells table are added to the spell list of your spellcasting class. (If you are a multiclass character with multiple spell lists, these spells are added to all of them.)
| Spell Level | Spells |
|---|---|
| Cantrip | chill touch, minor illusion |
| 1st | expeditious retreat, silent image, sleep |
| 2nd | crown of madness, darkness, shadow blade |
| 3rd | haste, nondetection, spirit shroud |
| 4th | dimension door |
| 5th | mislead |
Your spells might manifest in the form of shadows and whispers, creating blurry afterimages of your targets and even temporarily create dim ambient light as you cast them.
Suggested Characteristics
Shadowmasters of Telflamm are, by definition, members of a crime syndicate. Their devotion to Mask, the lord of Shadows, is a common trait, and tends to color their attitudes and practices. Shadowmasters tend to be cunning, ruthless, shrewd, and, most of all, deceitful. You can use the following traits to flesh out your shadowmaster character or to draw inspiration from to create your own.
| d10 | Personality Trait |
|---|---|
| 1 | Why tell the truth when I can get by only telling half of it? |
| 2 | I know more than people think, and I can’t resist hinting at it. |
| 3 | I enjoy basking in shadows and darkness; The closer to source of power I am, the better. |
| 4 | Insults and intrigue are my specialty. Words can do just as much, if not more, damage than a knife. |
| 5 | I’m quick to start a fight, and quicker to end one. |
| 6 | I am, what you might call, “a control freak.” I become nervous and irritated when things are out of my power. |
| 7 | I always look for anything to get me ahead or leverage over my enemies. |
| 8 | Fast-talk and doublespeak are my preferred styles of communication. If you can’t keep up, that’s not my problem. |
| 9 | I always have a plan for what to do when things go wrong. |
| 10 | I am always calm, no matter what the situation. I never raise my voice or let my emotions control me. |
| d7 | Ideal |
|---|---|
| 1 | Influence. By manipulating the world through the shadows, I can reshape it to my liking. (Evil) |
| 2 | Anarchy. There are few rules we actually need, and if the rest of the world were to see that, we would be truly free. (Chaotic) |
| 3 | Greed. The Shadowmasters are a means to an end, and that end sees me with all the gold. (Neutral) |
| 4 | Devotion. The will of Mask brings many blessings, by walking through shadow, I will be blessed. (Any) |
| 5 | Devotion. The will of Vhaeraun or Mask brings many blessings, by walking through shadow, I will be blessed. (Drow) |
| 6 | Control. Through our schemes, we can control the masses. (Lawful) |
| 7 | Punishment. Those that stand against us will be consumed by the darkness. (Evil) |
| d6 | Bond |
|---|---|
| 1 | One of the shadowlords has taken a keen interest in me, and I would do anything to impress them. |
| 2 | Mask has spoken to me directly, and I fear nothing more than losing his favor. |
| 3 | My family knows nothing of my role in the Shadowmasters and I would prefer to keep it that way. |
| 4 | I spared someone during a mission once. If the guild were to find out, it would be the end of me. |
| 5 | I am in love with a member of one of our rival guilds. |
| 6 | I will stop at nothing to achieve the rank of Shadowlord. |
| d6 | Flaw |
|---|---|
| 1 | I am quick to betray if it means my own gain. |
| 2 | I don’t have allies, only pawns and tools. |
| 3 | Everywhere I go, I seem to make only enemies. |
| 4 | I don’t trust anyone that says they want what is “good for everybody.” |
| 5 | The first one to run is the last one to die, and I don’t plan on dying. |
| 6 | My sharp tongue regularly creates trouble for me and my allies. |
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