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Shadowy Cloaks and Silent Daggers:
A Guide to Espionage in a Fantasy Roleplaying Setting

by Geoff Gander

A cool, drizzling rain beats gently upon the cobblestones of the dark, deserted street. Amid the susurration of raindrops blanketing every flat surface with a glistening sheen of water, the telltale "drip...drip" of water trickling from overhangs and eavestroughs echoes down a deserted alley. A sudden peal of thunder in the distance reverberates against the close-set buildings, and a flash of lightning illuminates a cloaked figure, leaning against a small shop. Deftly, the figure studies its gloved hands, and, without looking up, addresses the stranger who approaches it.

"You're late," says the cloaked figure.

"I know, I know. Couldn't be helped. I was detained by," replies the newcomer.

"I see. Have you brought the goods?"

"I have," says the other, patting a belt pouch. "Twelve rubies of finest quality in my possession, as stipulated by our contract. I will give them to you as a down payment for the job. The remainder will be sent to you by one of my associates once word of your success reaches me."

"Very well. Do not fear that I will fail. Your target is a very prominent member of Glantrian high society, and - needless to say - a wizard of considerable might. I have dealt with his kind before; he will pose no problems. Are you still leaving the actual details to me?"

"Yes. Do whatever you must, just get rid of him. I don't care if they fish him out of the canal the next morning."

"I am a professional, sir; I do not stoop to such crass measures. I think you will find my method most...fitting."

"All right, then. I hope you succeed."

"I always do," says the figure with a smirk, taking the pouch and turning to walk down the street.


When one thinks about the various prominent aspects of a fantasy roleplaying setting, some of the so-called "old standards" always come to mind: Lost artifacts to recover; ancient evils to put down; barbarians and dragons to slay; and the gratitude of rulers to earn. Although there is considerable scope for DMs to create long-lasting and memorable campaigns from these, and other, foundations of fantasy gaming, adventures set in a medieval- or renaissance-era world need not revolve solely around these. Part of the enjoyment to be derived from such settings is based upon the fact that, due to the presence of magic (to a greater or lesser extent), the inhabitants of those worlds are capable of activities that were impossible in our own until much more recent periods in history. One prominent example would be the prevalence of crystal balls - such an innocuous magical item could form the core of a magical news agency, whose reporters use such items to broadcast information at the speed of light around the planet. In allowing such a concept to exist in a campaign world, the DM has provided another facet to the world that could provide fuel for interesting campaign (perhaps with a decidedly "modern" flavour), yet still be grounded solidly in the fantasy gaming milieu.

Just such a concept - the addition of more modern ideas and events to a medieval fantasy world - is the topic of this article. What I will discuss and describe is the adaptation and insertion of espionage elements into fantasy roleplaying games - specifically Mystara. After reading this article, you will have acquired some familiarity with the types of settings, tones, and adventure hooks that predominate in such a genre - applied to the Mystaran setting. You will also have list of new skills, spells, and equipment to add to your campaign world, so as to bring such a genre to life.

Espionage - Theory, Practice, and Applying it to Mystara

Espionage, in its simplest form, involves the observation, infiltration, subversion, apprehension, or destruction of one party, object, action, or location on the part of the actions of another. Such a definition is by necessity a vague one, as there are literally no limits to the activities that might be carried out by a spy on behalf of his or her superiors: Assassination, theft, kidnapping, information gathering, surveillance, impersonation, and sabotage are all part of the classical spy's repertoire. Most people today are also familiar with the activities of espionage organisations in the real world, as well as those presented in popular literature and in the movies.

Granted that it is self-evident that espionage takes place in the real world, one might ask whether it would be possible in a fantasy equivalent. To arrive at a conclusion, one must only reflect upon what lies at the core of most espionage-based scenarios: Competition among organisations and nations, personal and group agendas, and political strife to name but a few factors. These are also present in a medieval world, as well. There are always rulers who wish to have their political opponents spied upon - or eliminated, organisations (religious or otherwise) who seek to advance their own agendas at the expense of others, and the potential for political conflict among nations is always present. As such, one can see that there is no shortage of work for spies in the medieval era. Such activities could take the form of assassinating a political opponent of the ruler, fomenting an insurrection, stealing valuable treasures and/or information, freeing prisoners who might aid the cause of the spy's employer, or performing reconnaissance missions deep within enemy territory.

Having first defined what one means when one discusses "espionage," and what such activities might involve in a medieval world, it is now possible to apply it to Mystara as a campaign setting. Even if one were to limit the focus to the Known World, there is clearly ample scope for espionage-related activities. The Principalities of Glantri, as an example, is rife with plots, counterplots, competing agendas, and strategic alliances - all working towards the goal of ultimate power over the entire realm. Similar observations could be made for Thyatis, with its grand imperial backdrop, and Darokin, with its tangled network of competing merchant houses. The common thread that runs through these three examples is that these shadowy activities tend to take place beneath the surface, whereas the nation itself may present a united front to the rest of the world; a resident of such a country might not even be aware of the extent to which the government or the various private interests might be in conflict.

Espionage-related activities do not always have to be of national scope for them to be applicable to Mystara. Smaller nations, or regions within them, could serve as the focus for the business of the spy. Certain regions of a nation, for example, might wish to obtain their independence, and employ spies to further their aims through sabotage, assassination, and information-gathering. Invading armies or hordes of bandits might employ spies to probe the defences of their intended targets. Another possibility is for one business to spy on the activities of a competitor. These latter examples could easily be applied to such nations as the Broken Lands, Karameikos, Heldann, the Isle of Dawn, Minrothad, or the Five Shires. In the end, almost any nation - or region thereof - can serve as a setting for an espionage-related mission.

Life as a Spy

The cloaked figure walked down the alleyway amidst the downpour at peace, knowing a good sun of money was headed his way. A pebble skittered across the refuse behind him, and, glancing our of the corner of his eye, he saw three shadowy forms creep out of the shadows.

"Saaaay, Osric! How's it goin' with the old cloak 'n' dagger outfit, eh?" asked one of them. "Me an' the boys back at the Black Tower were wonderin' what you were up to, ever since you cut an' left us two years ago..."

"None of your business, Cedric! I'm through with you lot - I told you then, and I'll say it again now, I no longer work for you! I'm in it for myself now, and doing quite well!" responded the cloaked man.

"Well, that may be so, but you remember those oaths you gave? The ones where you promised, under pain of death, to serve the Tower? Our boss, well she doesn't take kindly to students spittin' her in the face for her generosity, an' breakin' oaths that were meant to be kept. She's reeeal upset with you, Osric. A lot. Said to me, 'That Osric, he's cuttin' in on our business, runnin' that outfit that he does. An' to think that we trained him, too!' So she told me to grab some Breakerboys an' pay you a little visit, for ol' time's sake, an' to remind you who controls the spyin' business 'round here."

Flustered, Osric swiftly reached for his sword, saying, "Well, tell Ceinwyn that I have most assuredly not interfered with her business! I have only taken jobs in certain regions of Glantri - I know well where the Tower operates, and I stay away."

With a smirk, Cedric snapped his fingers, and Osric felt two pinpoints of fiery pain erupt in his back. Crossbowmen! His hands already feeling numb, Osric dropped his weapon and slid to the ground, his fading vision filled with the leering face of Cedric.

"You shoulda stayed with the Tower, Osric ol' boy," Cedric mumbled, patting the dying man on the shoulder, you wouldn't have had to die in an alley like this. Well, don't worry kid, it's just business." Letting out a chuckle, Cedric rifled through Osric's pockets, and located a small pouch, containing twelve rubies. Ignoring Osric's gurgling protestations, Cedric pocketed the gems, and walked away, whistling a catchy tune.


Even though spies can readily exist in a medieval setting such as Mystara, one must then wonder what sort of life they lead. Again, there is almost no limit to the variations; spies could be independent professionals, making a comfortable living from their contracts, or they could be part of a small cell of operatives working for a higher power - or perhaps they work for an independent organisation altogether, with its own agenda. Whatever the arrangement, each entails its own conditions, which will affect the life of the spy. Three such possibilities are discussed below:


Spies working for themselves can have great benefits, and many personal costs. The main advantage is that the spy reaps all of the financial rewards associated with his or her activities, and in doing so can maintain a very comfortable standard of living. Those of good reputation can even reach the point in their careers where they may have their pick among job offers available, selecting only the ones that offer the greatest challenge, or promise the largest reward. The down side to all this is that, as a "free agent," the spy has no protection or guidance whatsoever if they do not take the time to build up a cadre of allies, a task requiring considerable time and resources. There is no organisation from which assistance might be obtained if the spy encounters trouble, nor is there a co-ordinating body to assign the spy his or her missions. The "free agent" must do his or her own research and networking to find out where the jobs are. Unless he or she employs underlings to do such networking (which would be a drain on the spy's income - one can't just hire any bloke off the street), the spy will have to make him- or herself known to a prospective employer in some way, thus compromising anonymity. A further drawback is that, to prospective clients, there is no guarantee that a self-employed spy will not, a some future date, accept a mission that might harm their own interests, using the information gained during their current mission. As a result, many people might be reluctant to hire such a person, unless they can somehow be assured (whether by the spy, or by someone else - perhaps a rival spy or organisation) that they will not be placed in a vulnerable position in the future.

Perhaps the greatest difficulty faced by the "free agent" spy is becoming a spy in the first place; unless he or she is self-taught (highly unlikely), they most likely worked for someone - either an organisation or an authority figure of some kind - and subsequently struck out on their own. If this is the case, there could very well be "bad blood" between the spy and the former employer; in the cutthroat world of espionage, loyalty is a form of life insurance, and today's former employees could become tomorrow's competitors. Those that prove themselves disloyal, through treachery or striking out on their own, could compromise an organisation's interests in the future. Therefore, the most logical response is to eliminate them as soon as possible, before they can become a threat. Such realities make a self-employed spy's life a very dangerous one, in which staying in one place for too long a period could prove fatal, and in which one's clients could betray them for a better deal.

Working for an Authority Figure:

A second possibility is for the spy to work for a local power, such as a monarch, a prominent religious institution, a magical order, or a business. In this case, the spy will receive orders on a regular basis as to what activities should be undertaken, and in exchange they will receive a salary (usually quite high), training, and anonymity. Very rarely would the spy be in direct contact with the employer; an intermediary would most often be used instead. Veteran spies, or those who have proven their unquestioning loyalty, might be excepted from this arrangement, and be given their orders directly by the monarch, high priest, or other authority figure. The maintenance of professional distance between employer and spy protects confidentiality, and insulates the relationship from any of the politicking that undoubtedly goes on; otherwise, the spy might be reduced to little more than a pawn in internal squabbles. Such an arrangement ensures that few, if any, common citizens would know what the spy in question does for a living, save that they "Work for the king/church/company" - if even that much. Almost always, as a condition of employment, a spy will be forced to take an oath of secrecy, often enforced through a geas, designed to both protect the relationship with the employer, and ensure loyalty. Needless to say, the penalty for treachery is often death. Aside from that, however, the life of a "hired spy" can be a good one - so long as he or she remains loyal, and does not ask too many questions concerning who is calling the shots from above.

Working for a Professional Espionage Organisation:

Thirdly, a spy might be employed by a professional espionage agency. In this case, the agency would meet with potential clients in order to obtain contracts, and then dole them out to its operatives according to their experience and specialities. An expert climber and lockpicker, for example, might be assigned a job to sneak into the headquarters of a company and steal important documents or treasures, while a spy skilled in impersonation might be ordered to assume the identity of a prominent person and participate in a social function to obtain information. Regardless of the spy's skills, or the missions involved, the same relationship prevails: The organisation will protect and take care of the spy (i.e.: pay them and provide training) in exchange for loyalty. It might even operate a network of safe houses in certain regions of the Known World where operatives could seek shelter if necessary. As with the previous possibility, spies working in this sort of arrangement tend to be well-paid, as the organisation will often hire only the competent spies; incompetent ones tend to be weeded out through natural selection. Many employers are also not above liquidating their own operatives, should they pose a risk to security. In this sense, then, working for an espionage organisation is much the same as working for a higher power, though the primary difference is that the client changes frequently.

Aside from these three possibilities, there are certain conditions or circumstances that remain true for most spies, regardless of their working arrangements. Already mentioned are the expectations that spies will not double-cross their employers (if they do, there is a good chance they will not do so again), and that the tasks involved are many and varied. The average spy, no matter what his or her background might be, is expected to be creative, analytical, steadfast, and above all intelligent. When presented with a mission they are expected to devise a means to accomplish it in a logical manner - preferably one that minimises chance of detection. They are expected to place the interests of their employer above their own, but should their life be endangered, they should have the appropriate level of maturity and intelligence to alter their strategies, or to "pull out." A failed or abandoned mission is a lot less costly to an employer than a spy who has been killed or captured. Numerous other factors exist which affect the life of a spy; these, however, are discussed in more detail later in this article.


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Copyright 2000, Geoff Gander. All rights reserved. Used by permission.