The Oldest Art: Life in the Fellowship of Assassins

The Fellowship of Assassins, the assassins’ guild, much like their less prestigious cousins, the thieves’ guild, plays a vital role in the cloak and dagger games of big cities.

There is no story without conflict, and assassins are conflicts taken to the extreme: someone is willing to pay for a murder, and someone is there to pick up the contract.

How can hired killers be a fantasy trope? What makes this character so appealing? This not about chasing dragons. How can you use the assassin as a villain or antihero in your stories? What does an assassins’ guild contribute?

The Assassin

A successful assassin is exceptionally skilled, needs vast resources at their disposal, and relies on fear, notoriety, and secrecy for survival. Exceptional blade work is often required, but so is alchemy, disguises, and information.

Alchemy. Poisons, potions, and other alchemical substances are vital tools for many assassins. Knowing how to craft, prepare, and use these substances is key to ensuring a safe work environment.
Successful assassins’ guilds provide tutors or even keep dedicated alchemists on staff.

Disguises. Blending in and hiding in plain sight makes an assassin’s work much easier.
Applying a good disguise is more than just putting on a wig and new clothes. A proper disguise involves acting and learning the basics of a craft or profession to impersonate someone of that vocation. For instance, a waiter, servant, or lawyer, is expected to behave in a certain way, perform certain tasks, and perhaps even have certain views. A good disguise must take this into account.

Servants and Allies. The assassins can usually afford agents, spies, servants, and thugs to support their activities. These aides are either recruited by the assassin directly or through a guild.

Secrecy. Assassins are relatively few, and their number leaves them vulnerable compared to thieves. On the other hand, few numbers are also an asset as the assassin often needs to hide in plain sight.

Reputation. Some assassins bask in the notoriety and their dangerous reputation. Sometimes this both attract customers and scare off enemies, but few can do this successfully for long. Managing reputation, as an extension of secrecy, is key to the assassin.

The Masked Assassin. The secrecy and reputation balancing act lead many assassins to use masks, often with great effect. First, it protects the assassin’s identity. Second, a robust visual identity certainly adds to the assassin’s mystique, thus both spreading fear and adding to the assassin’s fee.

The Enemies of the Assassins

A skilled assassin would not consider law enforcement an enemy. Enemies imply personal investment – law enforcement is an obstacle, someone just doing their jobs, challenges to overcome. A law enforcement officer with private investment would naturally become an enemy.

Also, the targets are not enemies. Nothing personal, you see?

Individuals of other factions, as themselves or representatives of their organizations, are the assassins’ real enemies.

Rivals. Rivalries drive some assassins. Other assassins, factions, and individuals may hold personal grudges beyond what is “just a job.” Competition can literally be cutthroat, and plain work becomes vendettas.
The job can be a tool for personal power or the guild’s desire to rule.

The Nobility and Royal Council. Royal advisers and courtiers are involved in all kinds of plots, and often both employ or become assassins’ targets.

An adviser’s death can cast the nation into chaos or pass judgment on someone otherwise above the law. Removing the right courtier can save countless lives, at least in the eyes of their enemies.

Religious Sects. Religious murders are as old as religion itself. Sometimes the religious sects are at war with themselves, incapable of settling their beliefs.
The religious groups, like anyone else with a cause, recognize they are targets. This gives the clergy a choice: employ assassins themselves or fight them.

The faithful sometimes live troubled lives. The faithful are dangerous because they are not easily scared. They believe in a higher purpose and are many.

The Mage Guild. The Assassin Guild’s most dangerous rival is the mages. Mages’ power is astonishing and unpredictable. Worse, they can move unseen, strike secretly from plain sight.
Unlike more mundane enemies, they pose a real danger to the assassins – the mages is the one faction with more control of the battlefield than the assassins.

The Organization: The Fellowship of Assassins

The assassins, or at least the good ones, are few and may desire to organize for that reason. There is safety in numbers. There may also be an opportunity to create notoriety and emphasize the dangers of challenging the guild.

The Greater Good. Sometimes the assassins work for a greater good, or so some claim: the dirty deeds that need to be done to save and protect others.

Some assassins insist their work is apolitical, while others refuse this outright, which is strange as assassinations change policy most directly.
These assassins give up their humanity and make sacrifices, so civilians do not have to. Some assassins may take comfort believing the price they pay will make it worth it in the end.

The end justifies the means?

Guild Reputation. An assassin guild’s reputation is an important and ambiguous commodity.

The Fellowship often rely on their reputation for survival. Anyone who opposes the assassins’ guild must be powerful and prepared for severe losses to prevail – and few are. Most are happy to let others fight, and the Fellowship has deep pockets to pay those in doubt.

Many guilds rely on their reputations for continued survival. They thin the ranks of their enemies by scaring away the lesser threats and isolating the real ones, making them easier targets.

A good reputation also attracts customers. Anyone employing the assassins’ guild requires discretion, as failed assassination attempts alert law enforcement and, sometimes worse, the intended victim. A high success rate on accepted contracts is critical to the assassins’ guild.

Anyone employing the guild needs discretion and success. Failed attempts lead to counterattacks, law enforcement involvement, rumors, and all sorts of unrest.

A high success rate, which also means not accepting impossible contracts, is vital to the guild.

A Legal Front. Some guilds prefer to hide behind a legal front. This allows the guild to access parts of society reasonably unnoticed. The assassins can hide in plain sight and even include members unknowable of the organization’s real purpose. The front is also convenient for money laundering and retirement plans.

This front can be almost anything, for instance:

  1. The City Watch. The assassins are law officers. This means they investigate their own murders, can demand information and access at their leisure, and tamper with evidence.
  2. The City Hall. The assassins hide among sewer workers, city sweepers, renovation, city hall staff, advisory staff, and city councilors. This gives access to locations, information, and the ability to show up almost anywhere unquestioned.
  3. The Caterers and Entertainers. Supplying food, drinks, and entertainment for events give access while being taken for granted. Entertainers and servants are often underestimated and ignored.
  4. A Bank. Collecting debts is tricky, particularly in a world of magic, and who can do it better than an assassin? The banks lend respectability and power to the guild’s front and opportunity for money laundering. The combination of financial and assassination services also makes the guild a perfect partner for both crime and many governments.

A Morbid Romantic Flair. Some assassins cultivate a morbid romantic flair about their business. What first created this notion is unclear, as we are talking about murdering people for money, but perhaps the detached skill and the fatal duel have a unique appeal.
This romance is something the guild can exploit. Some will underestimate the guild, while others are attracted to them, and all will be uncertain what the guild is all about.

Government Agents. Some assassins work for the governments. Royal assassins, or agents with a license to kill, if you would believe such a thing exists.
This particularly bleak branch of government protects the greater good, so everyone else is safe.

Death Cults. Perhaps the most sinister assassins are the ones killing for religion. Killing for money is undoubtedly morally bankrupt, but someone killing for a god is truly deranged.
It is difficult to say who’s more dangerous and appalling: the religious assassin or the non-believer assassin.
Another disturbing variant is the assassin who becomes obsessed with the killing itself, akin to the Slayers.

The Assassins’ Guild as an Employer

An effective assassins’ guild needs members, agents, spies, servants, and contractors.

  • Tailors, wigmakers, and cosmetics crafters.
  • Alchemists and poison makers.
  • Spies and informants.
  • Thugs, guards, and soldiers.
  • Teachers and researchers.

The best twist of all is that most guild servants may not know its real purpose while still be bound by the code of silence surrounding it.

Ten Contracts for the Assassin

So, what does it mean to be an assassin? There is enough work to go around to pay the assassin’s bills.

Choosing employment as an assassin means accepting contracts and making unusual contacts. Ten contracts or contacts for the assassin:

  1. The Foreign Dignitary. A foreign dignitary – perhaps a noble, ambassador, or powerful landowner – is visiting. The dignitary’s death will disturb the balance of power and perhaps bring some much-needed justice. Any fallout is not a concern for the contractor.
  2. The Political Orator. A commoner has raised concern in public and gained a following. Unrest is growing, and people question the status quo. The rulers and wealthy need this demagogue removed.
  3. The Bullheaded Noble. A noble has overstepped and become a target. Bullheaded arrogance, casual cruelty, or dangerous ambition – it does not matter. Someone, somewhere, has had enough.
  4. The Dangerous Witness. A civilian has witnessed something dangerous and compromising, and word got out.
  5. The Enterprising Merchant. A merchant has grown too ambitious for the established order. Those on top do not like change.
  6. The Lonely Gangster. A criminal, or even a crime lord, has made mistakes and become a target of rivals.
  7. The False Prophet. A clergy member postures a new interpretation of the holy scripts, and the new dogma is deemed dangerous. Heretics upsets the established power and are not accepted.
  8. The Rising Star. An emerging leader, a voice of youth and change, is rising and threatens the old guard.
  9. The Ambitious Wizard. An ambitious wizard has become a threat to others in power. Imagine someone of exceptional skill, instead of inherited money, rising to power? Some may object.
  10. The Problematic Ruler. Some factions seek a change in the government, and a peaceful transition of power seems impossible.

Contact one day, contract the next. Fate can change swiftly when dealing with assassins. Anyone looking to destroy the assassins’ guild may want to ally with these folks.

Rewards, Gear, and Treasures

Assassins are expensive, thus making them the tools of the already wealthy and powerful. The money involved also puts powerful tools, numerous agents, and other resources at their disposal.

Gold. To some, hard currency is the only acceptable payment.

Land and Titles. Some rulers may strike a bargain, offering something of little value to the ruler, but with a greater value to all others: land and title.
This has the additional benefit for the ruler that it makes the assassin a long-term collaborator. A wise assassin sees this and accepts with caution.

Secrets. The best and often most dangerous assassins have no use of money and desire secrets as payment. They are likely to prepare for something, build some kind of case, or – most dangerous of all – work for a greater good.

Favors. Another dangerous fee is the favor. This implies two things. First, the assassin is confident in the ability to collect. Second, the assassin has an ulterior motive.

Corrupted Assassins?

An assassin’s life and work are demanding, and burn-out is a real danger. Few assassins grow old or end up in dungeons. Stressful, no doubt, they usually die on the job.

Retirement. Retirement is a precarious proposition for an assassin. A former assassin remains a security hazard and is, for some guilds, simply not acceptable.

Redemption. Some assassins live to regret their actions. Mistakes were made, and maybe options few. Can murder for money be forgiven? Is there merit in trying?

Related Posts

Reading List

Apparently, assassin fantasy books are a sub-genre of its own, and fictional assassins have their own category on Wikipedia.

I thought “assassin fantasy” was limited to Robin Hobb and perhaps Sarah J. Maas, but it turns out there are shelves of books that may qualify.

A personal favorite is Brent Weeks’s The Perfect Shadow (2011), an excellent little stand-alone. I do not recall many assassinations in Scott Lynch’s The Lies of Locke Lamora (2006), but it remains one of my absolute favorite fantasy novels.

I clearly need to re-read Hobb.

Many roleplaying games, including most editions of Dungeons and Dragons, includes assassins as player options, although without exploring what these characters actually do as player characters.

Got any reading tips? Let us know in the comments below!


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