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The Icratic empire and the Noctan Empire, both powerful empires, are fighting a war. The Noctan Empire has physically well-built soldiers that are well suited to the terrain they are fighting in, but they have to go against wyvern-riding cavalries and soldiers with enchanted weapons. After losing three consecutive battles, the Noctan emperor seeks help from a certain infamous group. The group is an independent, relatively secret group of well-trained assassins.


The setting is medieval fantasy with magic, potions, and enchanted weapons. Both armies are structured just like any other medieval army (except the fantasy parts).

The assassins

  1. will receive missions like spying and killing important generals (or other figures) of the opposing empire
  2. will not use poisons; poisons are easily detected.
  3. won't be fighting on the battlefield. They will only carry out stealth missions.
  4. are well-trained for combat.

+The Icratic Emperor suspects that assassins are working against them, and made sure their generals are well guarded.

Will the assassins be able to help the emperor win the war, or at least drag it on?

To be more specific, will the assassins be successful with their missions, and if so, would that have a huge impact on the tides of war? As in, will killing off generals in a medieval army have a big impact on the war?

Assassins play a major role in fiction; I was wondering if they could also be a big influence in a realistic medieval setting.


Edit Apparently the question was closed because it was too "story-based." My intention was to ask how figure-dependent medieval armies were, and if assassination is a good strategy in war, realistically speaking. However, it seems like I didn't do a very good job conveying this intention and caused some confusion.

The story details are just an introduction to the question; don't worry about it when answering the question.

To remove some confusion, I edited out some parts.

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    $\begingroup$ "Poisons are easy to cure". Really? Even modern medicine at its best, with dialysis etc, has difficulty treating arsenic poisoning. Which is a commonly available, tasteless and mostly odorless poison that can be added to food, and a guaranteed lethal single dose is as large as your pinky's fingernail. Ok, your world your rules, but this one is a stretch. There is a reason that "food taster" was a thriving but risky career line since ancient sumerian times. If you are in a medieval-with-magic scene, consider rater making poison detection device/spell/whatever commonly available. $\endgroup$
    – PcMan
    Oct 12 '21 at 6:21
  • $\begingroup$ @PcMan I was thinking of specially designed healing potions, but your idea sounds much better! Thanks for the suggestion :) $\endgroup$
    – Yellow
    Oct 12 '21 at 6:41
  • $\begingroup$ Does infiltrating the enemy command center in the middle of an ongoing battle count as ‘fighting on the battlefield’? Because if not these guys sound perfect for a decapitation strike. $\endgroup$ Oct 12 '21 at 13:39
  • $\begingroup$ "chivalries"? Did you mean "cavalries"? $\endgroup$
    – Sam Dean
    Oct 12 '21 at 13:55
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    $\begingroup$ There are 4 votes for closing as 'too story-based' and not even one comment explaining the vote. It seems that these days all questions that mention backstory are treated as 'too story-based'. This question is not about a plot, a story, or the actions of specific characters. This is a question about the military and specifically about the assassin division and its utility. $\endgroup$
    – Otkin
    Oct 12 '21 at 17:33
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If they will be successful with their mission is entirely up to you, since it's your story.

However, being in a medieval setting, taking out a key figure in the opposite side can surely have a greater impact on a war. In those times organization and hierarchy was less of a factor, and wars relied more on the leadership capabilities of the people leading the army to inspire the soldiers. And often those people were mercenaries, meaning that they fought for the money, not for the flag. So, breaking a single link in the short chain can surely have a big impact on a war.

With the abilities you have given them they can easily avoid the safety measures which were possible in medieval times and strike.

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    $\begingroup$ Given the pseudo-medieval (and I infer, feudal) setting, assassinating leadership and their lieutenants may actually be more effective than it would be in the modern day. $\endgroup$
    – Ruadhan
    Oct 12 '21 at 15:44
  • $\begingroup$ @Ruadhan For the better or the worse? Feudal system meant that the Baron qualifications for leading an army was being the son of the previous Baron. While aristocracy were trained for warfare, and peasants were not, sustituing aristocracy leaders for whatever who was available and had some war experience can actually improve the outcome with about the same probability as hindering it. $\endgroup$
    – Rekesoft
    Oct 13 '21 at 8:09
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    $\begingroup$ @Rekesoft A very good point. Assassination as an effective tool requires a good sense of consequences. If the enemy relies upon an individual's skills and knowledge, then killing that individual will kick a major support out from under the foe. But if that person's lieutenants can take up the slack or do a better job, it may be better to kill them too. Effective Assassination is basically exploiting Bus-Factor for your advantage :P $\endgroup$
    – Ruadhan
    Oct 13 '21 at 10:17
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A way better strategy than a quick assasination:

  1. infiltrate the camps under pretense identities and scout the terrain and the habits of the victim. Very likely a professional assassin will need to do this anyway
  2. kidnap the victim instead of just killing him. The closer to a major attack or invasion the better, not enough time to find a replacement
  3. let the opposing army know the victim is still alive and keep them on the search and chase for a week or so.

This will create a far more waste of resources than killing the general (or key person) outright - not only it will freeze any attempt to replace the person with the second in command (and attempt to carry on the attack anyway, even with suboptimal tactics), but it will bind significant forces in the search party.

You may keep it for some days to a (very few) weeks, maybe time enough to fortify your positions and reposition your forces.

Now, at the end of the farce, still do not kill your kidnapped - let him to be found in a drug induced comma from which he'll wake up disabled.
Well dosed methanol will blind him, carbon monoxide poisoning can lead to loss of memory, a few miligrams of dimethylmercury will drive them mad in about 3-10 months time (now, that's a bit of stretch to prepare in medieval conditions. But feel free to to try other ways of mercury intoxication, just make sure the doses are not immediately lethal).

The idea is to let them hope they'll be able to recover their precious human resource for as long as possible: tending a wounded and disabled soldier will always cause more cost for the country that sent him than killing him outright - and generals are no exception.

Letting the 'cost of wounded' aside, the attacking country will need to deal with the "PR disaster". Usually the generals are presented to their population as legendary heroes who, if they eventually fall, will fall in heroic battles. I don't want to be the ruler who needs to cover up for one or more missing heroes for 3-5 months while still trying to sell their population a war that seems to go nowhere.

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  • $\begingroup$ This answer feels like "yes, killing leaders will obviously work" with a note that maiming them instead would be slightly better. $\endgroup$ Oct 12 '21 at 22:21
  • $\begingroup$ @OwenReynolds This answer says a lot more, but for one that isn't prepared to understand timing, logistics and attrition in the context of a war, the things that this answer says will likely be missed. $\endgroup$ Oct 12 '21 at 22:40
  • $\begingroup$ Creating martyrs very often backfires badly. Acting in an underhanded way (releasing someone but permanently crippling them) is also likely to backfire in the long term as no one, not just Noctan's current enemies, will trust them to behave with integrity. This looks like a way to win a battle but lose this war and weaken Noctan long term. $\endgroup$ Oct 13 '21 at 0:10
  • $\begingroup$ @KerrAvon2055 Hard to switch from a "hero" image to a "martyr" when your hero got captured from inside his camp by forces unknown, no treason involved. If the Noctan empire was the aggressor, they can lose no more of their credibility - they are potential aggressors for anyone and they are to be feared - they weren't after winning love when they attacked anyway. If they were the defending ones, well, they just thwarted an invasion/campaign/etc by disabling just one or two persons - battle cancelled, everybody lived and left for home; gee, even the disabled persons lived! $\endgroup$ Oct 13 '21 at 0:43
  • $\begingroup$ Probably better than the wasted resources on the search for and later care of the incapacitated general (which would be relatively small compared to the resources needed by the entire army anyway), is the fact that by kidnapping the general you may be able to get information, and the other side has no idea how much of their secrets are now known. Do they assume their strategic plans are now all known to the enemy and invent new ones from scratch? They're probably already heavily committed in terms of troops raised, provisioned, and positioned, and time spent. $\endgroup$
    – Ben
    Oct 13 '21 at 1:20
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Sabotage the advantages of the opposition.

Killing is so obvious. If someone important gets killed then you know assassins are around. Subtle sabotage is better because you can keep it up longer, and it is more fun to write.

  1. Give potions to the wyverns. The tack for the wyverns is doped with potions that make the wyverns go into heat about a half hour after they are saddled up. Some of the potion gets on the riders too.

  2. Swap out enchanted weapons with lookalikes. The lookalikes are enchanted too but they do more interesting things than the hard killing. Things their users will not appreciate but readers will.

  3. Sabotage spellcasting equipment. Ideally in a way that causes the opponents to be suspicious of their own spellcasters, because why would those wizards have the makings for wedgie weapons, and that dang heat potion is still on me, I think.

  4. Doppelganger. Mission Impossible style. The assassins can change their appearance to look like persons in the enemy camp. They are not shapeshifters - these are just disguises. Perhaps one of the aforementioned spellcasters? Or a person from one squad sneaking around a rival squad's barracks? Foment discord. Make them suspect everyone.

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It really depends, on strategy, locality, ideology, tactics and logistics.

If the ideology of the faction is self-perpetuating, taking out a leader, will merely change nuances, but a religous conquest might still continue, for it is written. Nobles and kings are, actually very non-ideologic, as when the conquering king dies, the board is reset and the army goes home.

When a army is already home, the war will still continue, because you fight for your home, no matter who is up top or not. Local defense trumps all other elements.To take out a strategic important general, may collapse a whole campaign, depending on the training of the troups and the military paradigm. Family sized units, trained for autark action will march on. (Google Nord Bat2) for a explenation. Large armies with huge supply chains will not march on, but go to the next in the chain in command (usually a underfoot figure) and thus return home, or wait in place for the subordinate to be replaced.

A medieval army can have a "life" of its own, in that removing the controlling character, actually might unleash its full damage potential. Means plundering the countryside, falling apart into bands of mercenaries and other horrors. Such a army might not even have a home, and tour the countryside indefinatly like a circus of death, until it meets opposition.

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The Icratic Emperor suspects that assassins are working against them, and made sure their generals are well guarded.

Unfortunately, this left the Icratic Emperor themselves wide open to assassination.

After the Emperor did not wake up one morning, the next in the line of succession assumed the throne. Military efficiency suffered a bit as the new Emperor reorganized some departments, recalled some generals, promoted others, and generally imprinted their vision on the war.

Two weeks later, the new Emperor was assassinated.

This time, the heir was not quite so well prepared. After all, they were only the second in the line of succession, so everybody thought they might have a few more years for their preparation to take over responsibility.

Which was probably why the new Emperor forgot, in all the confusion, to update their personal security. Well, perhaps one contributing factor was that the head of the household guard had noticed a pattern... and after the most recent Emperor was also offed three days later, said head of the household guard wasted no time in declaring themselves Emperor.

Then again, the no-longer-reigning family still had a lot of loyalists, who definitely did not appreciate this kind of usurpation, especially as there was an (underage) claimant to the throne who was distantly related to the three late Emperors. The loyalists pulled their troops from the war (wait, was there a war ongoing? One can't quite remember, with all the confusion...) and marched on the capital.

A few Icratian Emperors later, the Noctan Empire moved in and mopped up what was left.


TL;DR: don't kill the generals. Kill the Emperor and watch potential successors kill each other.

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A lot depends on which individuals are key to the Icratic war effort, and whether the Icrations or the assassins do a better job of identifying them.

The most obvious thought is the generals. Obvious to the Icratic generals, anyway. And it may be true.

Does one of the generals depend on a staff officer to do all his thinking for him? That's a target. And one the officer will be reluctant to properly protect.

Is the Icrations' knowledge of Noctan territory contained in the heads of a few scouts? Targets.

Are there aspects of the Icrations' logistics that only a single individual understands? This happens quite often in large, underappreciated organizations.

Many premodern armies depended on independent contractors for a lot of their logistics. Such people might be less guarded than actual soldiers. Or more willing to outright sabotage the war effort to recover their families intact.

Similarly, are there special skills needed for caring for wyverns? That sounds like the sort of job that requires serious training. If there's any task that all wyverns need frequently, but only a few specialists know how to do: targets.

ETA: If the assassins are taking advantage of a blind spot in the Icratic command culture, they'll want to kill a few random people as well to avoid calling attention to their actual targeting.

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A lot depends on fine details of your setting. I will assume a mostly medieval setting where magic does not play a major role and does not change the world too much.

Your key is communication and time. You want to take out the right person, at the right moment, because it takes a long time to send a message anywhere (days or weeks).

That right person doesn't have to be a general. Those are well guarded. A messenger with the march orders for the army who disappears will not be noticed for a while. Likely, they will send two or three because of wolves and other dangers on the road, but your assassins shouldn't have issues eliminating them all.

If you want to kill a general or other important figure, you want to do it at the right moment, when he is about to make an important decision and before he can communicate it. If nobody knows if the general wanted to besiege the city or not - who will make that decision in his place? And can you arrange things so that it will be a more cowardly person?

Assassins by themselves are a nuissance in war. Much like modern snipers, they are hated, feared - but rarely decide a battle, much less a war. But if you have threats to the enemy behind the scenes, you can force him to keep troops at home that he could otherwise use against you. Every one of your assassin can bind a hundred soldiers in this way. That's well worth it, plus the trouble they can stir up can do even more harm.

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