How would you build an actual assassin?

[dehro]

Reading up things online, i started thinking of how to build a workable solitary assassin.

As a concept I'm thinking of someone whose entire training and natural talents are geared towards infiltration, assassination (either up close or by ranged attack but anyway it should be a mundane/physical attack), followed by escape.
Inspirations would be Waylander the Drenai, your garden variety ninja the assassin's guild from Discworld, The way of Shadows series... It would have to be a character where whatever magic is used should be primarily one of deception, leaving the actual assassination to more mundane means

This would either be a high level statted out opponent NPC, who operates alone and it's a thorn in the side of the main party, or maybe even a playable character.

For race I'm thinking human variant, changeling or half elven... But other than that I'm very unsure.
It could lean heavily on the rogue assassin, on one of the bardic schools (there seem to be several that fit the ticket), on fighter...

What would your take be and what would your progression look like?

[CTurbo]

I love this. I've thought about it before and it's a character I want to play one day.

You need at least 3 levels of Rogue for Assassin, but really both the 9th and 13th level features would be nice to have too.

I think some Warlock would be a perfect fit. I would personally choose GOO for the telepathy. The target you're speaking to doesn't have to know where the voice is coming from. I would definitely choose Bladelock. This character needs to be able to be unarmed while also being able to be armed when needed. Bladelock is perfect for that being able to summon a weapon in an instant and then make it vanish. Warlock has several really nice invocations for this concept too.

Armor of Shadows. Since you won't ever be wearing any armor, this would come in handy.
Beguiling Influence. Deception and Persuasion skill prof are necessary.
Devil's Sight. Seeing through any and all darkness would be handy.
Eldritch Sight. Being able to cast Detect Magic at will would be really nice.
Mask of Many Faces. Disguise Self at will!! Enough said.

For race, human, half-elf, or changling would work. This build doesn't really rely on any feats, but Alert and Observant would be really nice to have. You want a high Dex and Cha though for sure and at least a decent Wis. Con is not as important here, because you are not going to be in combats or at least not how I envision it. Even still with half-elf you could start 16 Dex, 14 Con, 13 Wis, and 16 Cha. Grab Observant to bring Wis up to 14 later. Vhuman could start with Observant and 16 Dex, 12 Con, 14 Wis, and 16 Cha. Being able to cast Disguise Self at will pretty much makes changling unnecessarily redundant.

[Rolero]

Changeling should be the race to go, no discussion. The ability to change your appearance at will is bonkers. Also, you get two of the basic skills you will need and free expertise on a tool.

Hexblade Warlock eases the MADness and nets you some nice tricks.
Rogue is a no brainer, Assassin or Arcane trickster are solid choices. If you you want a focused one strike / one kill from the shadows or a disguise, the instacrit of the assassin combined with sneak attack and an eldrith smite from the warlock can skyrocket the damage.

Some quick math. Lets say, Assassin 3 / Warlock 5 (the bare minimun to pull this off) with a typical rapier for base weapon damage:

Wpn 1d8 x2 + Sneak 2d6 x2 + Smite 3d8 x2 = 8d8 + 4d6 + modifiers = damage around 50-60. Not too shabby. Also, you could add poison too.

Infiltration wise, Mask of many faces + Changeling + Actor feat, and you can impersonate anyone with impunity.

To reinforce talents, continuing his career as a bard is a solid choice, either Lore for cutting words and extra spells or Sword college for extra attack and extra damage with the Blade Flourish.
You will get extra spells to reserve your warlock slots for the smites or emergencies, extra skills and new useful tricks. Also, getting up to level 3 spells will grant you Nondetection, which will help a lot to keep your cover.

A very high level character with this plan could look like this:

Rogue (Assassin) 7 / Warlock (Hexblade/Blade pact) 5 / Bard (Lore or Swords) 6

The high level features of the Assassin are useless thanks to the Changeling and Warlock powers, so stopping at 7th level is more than enough to get most of the Rogue goodies.
You only need Eldritch Smite and Mask of many faces, so more levels on warlock don't give enough reward for the investment.
Instead, continuing as a Bard gets you lots of new utility tricks.

One piece of advice though, this character is not a head on combatant. If you intend to use it as a recurring npc/rival of the party, abuse hit and run tactics. The build has enough potencial to decimate a PC on 1 turn and vanish the next round or disguise like an ally of a pc and take him by surprise.
But if he/she is discovered and lock into combat, the main priority should be escaping at counterattack later.

At the presented 18th level, an ambush with a completly dedicated build to damage on surprise round, could look like this:

Rapier 1d8 x2 + Booming blade/Green flame blade 3d8 x2 + Sneak attack 4d6 x2 + Eldrich Smite 3d8 x2 + Blade Flourish 1d8 x2 = 16d8+8d6+Modifiers = easily over 100 damage plus the nastiest poison you can get (at this level, getting Purple Worm Poison should be more than possible, increasing the damage by 12d6 x2 with a DC of 19 to halve that, again, not too shabby) Also, bonus points if you can get a powerful magic weapon to up the damage even more.

Pros of this build:
-Master of infiltration, almost undetectable
-Can impersonate anyone
-Proficient in all the relevant skills for an assassin/spy and with 7 expertises available
-Insane nova damage
-Lots of utility abilities and spells

Cons of this build
-Glass cannon
-Especilist on hit and run
-Magic resources can get quickly scarce on a long day
-Lack high level spells and powers, may unbalance the party

[Democratus]

Methodology is also important. Assassination generally implies killing someone of importance.

They might have access to magics that could foil your attempt (speak with dead, raise dead, etc.). Assassins in my world who want to make sure the job stays done have 2 standard methods.

After killing the target:
1) Cut off the head and escape (can't raise, or speak to, dead without the head)
2) Animate the body as undead and have it escape with you (can't raise dead if subject is undead).

The Assassins Guild in my world has a "prison" that is filled with skeletons and zombies of their victims. The prison exists solely to block resurrection magics. This is part of the Guild Guarantee(tm): "If we kill it, it stays dead!".

[Corran]

After killing the target:
1) Cut off the head and escape (can't raise, or speak to, dead without the head)
2) Animate the body as undead and have it escape with you (can't raise dead if subject is undead).
Disintegrate works too (though it's harder to get access to it).
Edit: Soul cage too. Nvm, duration of only 8 hours.

[Dr. Cliché]

Might depend a little on the theme.

e.g. you mentioned Discworld assassins and they tend to be well-trained but (barring one or two exceptions) lacking in magic. Either pure Assassin (maybe with the Noble background) or some combination of Assassin and Monk (for the various not-quite-magical tricks and abilities) might be appropriate. Perhaps 6+ levels of Shadow Monk for Mr. Teatime.

However, for the world of D&D, I think Assassins would greatly benefit from leaning more to the magical side of things. That gives you:
- Ways to disguise yourself.
- Ways to ascent to high windows.
- Ways to make yourself invisible and unheard.
- Ways to teleport past walls - either for entry or a quick getaway.
- Ways to disable/incapacitate a target from a distance.
- Ways to magically trick or ingratiate yourself with guards or staff ("Hello, my good chef. Why not try some of this rare spice in your lord's meal tonight?").
etc.

Warlock definitely seems like the perfect choice for an Assassin. It gives you access to most of the above, including potentially being able to change your face at will. Plus stuff like being able to naturally see through darkness of all kinds. You've also got the option of an invisible familiar to scout out places for you.

I think I'd always want to have at least some levels of Warlock, but if I was willing to multiclass:
- Rogue/Assassin would gain you extra movement/mobility and also extra damage if you catch your target by surprise. Though I think it's worth remembering that attacking your target isn't the only way to kill them. Poisoning their food or wine could work just as well, whilst also allowing you to be long-gone when they actually succumb. Depending on the circumstances, you might be able to just use the aforementioned familiar and never actually need to set foot in their house yourself.
- Monk is also possible for some useful skills and abilities, though I don't think it would mesh especially well with the Warlock.
- Bard gives you additional skills as well as a variety of useful spells. It also gives you an innocent reason to be in a lord's house, as you could simply ask to play or perform for his lordship in some manner or other (not always necessary but could come in handy for more long-term projects).
- Sorcerer has spells and, more importantly, Subtle Spell.

Oh, one other interesting possibility (and the only one I probably might not mix with a Warlock) would be a Druid of some sort - simply because shapeshifting into an animal gives you some interesting options when it comes to assassination.


As an aside, this thread makes me thoughtful in a Tippyverse sort of way, simply because of the sheer number of angles a powerful lord would have to consider in order to fend off would-be assassins. :smalltongue:

[dehro]

Very interesting concepts...so much to tinker with.
Some of these could really mess up a party purely because of the induced paranoia...

[dehro]

Would it be possible for a character of this kind to be effective also from range, or would he have to commit to one path or the other to not fall utterly behind?

[Warlush]

Would it be possible for a character of this kind to be effective also from range, or would he have to commit to one path or the other to not fall utterly behind?

Well both Rogue SA and auto crits work with a long bow, and XGtE gives Bladelocks the ability to create long bows. So yeah with the Sharp Shooter feat you can be even more deadly at range than up close. While still being able to Hex and stab somebody in the back twice. Oh and both work with Eldritch Smite, which also doubles on a crit.

[Specter]

I've always thought of assassination when I see Subtle Spell. Like, you can just walk past a person and cast some necrotic crap and no one would even know he was assassinated!

[dehro]

I've always thought of assassination when I see Subtle Spell. Like, you can just walk past a person and cast some necrotic crap and no one would even know he was assassinated!

I was thinking about that in the context of giving the target disadvantage in the con save for the assassination/death strike attempt... But I haven't found a way yet to pull that off whilst maintaining the surprised status

[SLOTHRPG95]

Drawing on the Ankh-Morpork Assassin's Guild, at least as a starting point, I'm thinking VHuman (Actor) Noble Assassin Rogue 3/Whispers Bard X. You start off with a solid basis in mundane infiltration and assassination, and an upper-crust education which is necessary for the Discworld feel. Then you branch out into a slew of magical tricks, and at 9th you gain access to Actor + Mantle of Whispers, which is a super fun and potent combo that I've put to good use (on a single-classed Whispers Bard, admittedly). Further buy-in to more powerful Psychic Blades is basically only making up for lost SA, not netting you damage compared to a straight Assassin, but there's too many good infiltration/escape spells as you level to regret going back: Dimension Door, Greater Invisibility, Dominate Person, Teleport, Glibness, etc. Being able to Foresight cast on yourself before executing a hit seems like a great capstone.

[Lunali]

If I wanted to play an actual assassin, I would try to get people to play a different system. D&D's combat system narrative is designed around wearing down your opponent's luck until you can land a fatal blow. This narrative doesn't lend itself well to the assassin that delivers a single critical blow.

Now that I think about it, you could do an assassination mission as skill based combat, with either side taking actual hp damage as the mission progresses, even if they aren't personally present at every interaction that causes their misfortune.

[Dr. Cliché]

If I wanted to play an actual assassin, I would try to get people to play a different system. D&D's combat system narrative is designed around wearing down your opponent's luck until you can land a fatal blow. This narrative doesn't lend itself well to the assassin that delivers a single critical blow.

That is an important point, I think.

D&D lends itself to some rather odd situations - like having a target who's incapacitated or even completely immobilised and still being unable to deal him a single, fatal blow.

Also, poisons (a favoured means of assassination) are almost universally weak and - in spite of their name - most aren't even fatal. :smallconfused:

[dehro]

in past editions you could always coup de grace someone... that's not a thing anymore, sadly, if not by DM fiat. maybe a houserule...

[Sparky McDibben]

It would be setting-dependent, but I love the guy you see coming. For example, in a "high-honor" society where a leader must accept challenges to his reign, or where trial by combat is acceptable, I'd use an assassin who was a straight champion fighter. Walk up, call someone out, and kill them in the square. If they send a champion, kill the champion first, then re-issue your challenge. There's an episode of the BBC's Merlin where the BBEG wakes up a death knight who basically does this. Bonus points if you take Magic Initiate for disguise self to issue the challenge as someone relatively non-threatening (like a Disney princess, or even the target's rotund and non-combative son, Samwell Tarly).

If the fight is to first blood, use poison. If they refuse to accept your challenge, hire a bard to write mocking tales of the proud king "who boldly ran away, away." If they survive your first strike, hire a more traditional assassin to kill them as they recover.

Another good one would be a druid. A combination of Wild Shape and/or polymorph could be very effective. You sneak in as a spider or mouse or something, then BAM! Wild Shape into a Giant Poisonous Snake in the victim's bed for some sweet, juicy poison damage. Even better, come out of Wild Shape, polymorph the victim's spouse/lover into a deadly creature and spook it with something so they attack and kill their own lover. Or, come out of Wild Shape, polymorph the victim into something easily carried, Wild Shape into a hawk, fly out the (presumed) window, fly up about 300 feet and drop their ass onto something spiky. Like a lance rack. Or Ye Olde Edgelord's Armoury.

[Corran]

It would be setting-dependent, but I love the guy you see coming. For example, in a "high-honor" society where a leader must accept challenges to his reign, or where trial by combat is acceptable, I'd use an assassin who was a straight champion fighter. Walk up, call someone out, and kill them in the square. If they send a champion, kill the champion first, then re-issue your challenge. There's an episode of the BBC's Merlin where the BBEG wakes up a death knight who basically does this. Bonus points if you take Magic Initiate for disguise self to issue the challenge as someone relatively non-threatening (like a Disney princess, or even the target's rotund and non-combative son, Samwell Tarly).

If the fight is to first blood, use poison. If they refuse to accept your challenge, hire a bard to write mocking tales of the proud king "who boldly ran away, away." If they survive your first strike, hire a more traditional assassin to kill them as they recover.
I've seen that episode. Summon greater demon (for a Dybbuk (https://forums.giantitp.com/showthread.php?563313-Summon-Greater-Demon-Dybbuk-Potentially-Better-Animate-Dead&highlight=summon+greater+demon)) could help here, as it will allow you to risk less by not actually taking part in the duel (assuming the direct approach you mentioned is not a goal in itself), and punch above your weight (by having someone more powerful than you fight in your place; whom you killed because you fought them in favorable terms, eg surprise, having powerful allies backing you, etc). So for example, you could kill Lancelot and have him challenge King Arthur (we all know how that went though, but at the very least you cause some strife and paranoia in the court), all the while hoping that Merlin is not there to see through our cunning plan and stop it.

Even in less ''high-honor'' settings, the Dybbuk could still prove useful for gathering information and sometimes even for infiltration purposes (though it's very time sensitive for the latter, at least without something like a planar binding -or depending on RAW, a necromancer/oathbreaker paladin ally- backing it up).

[Sparky McDibben]

I've seen that episode. Summon greater demon (for a Dybbuk (https://forums.giantitp.com/showthread.php?563313-Summon-Greater-Demon-Dybbuk-Potentially-Better-Animate-Dead&highlight=summon+greater+demon)) could help here, as it will allow you to risk less by not actually taking part in the duel (assuming the direct approach you mentioned is not a goal in itself), and punch above your weight (by having someone more powerful than you fight in your place; whom you killed because you fought them in favorable terms, eg surprise, having powerful allies backing you, etc). So for example, you could kill Lancelot and have him challenge King Arthur (we all know how that went though, but at the very least you cause some strife and paranoia in the court), all the while hoping that Merlin is not there to see through our cunning plan and stop it.

Even in less ''high-honor'' settings, the Dybbuk could still prove useful for gathering information and sometimes even for infiltration purposes (though it's very time sensitive for the latter, at least without something like a planar binding -or depending on RAW, a necromancer/oathbreaker paladin ally- backing it up).

That's somewhat ingenious!

[Maelynn]

When I first read the description of the Bard's College of Whispers, I immediately thought it would make a great assassin. The kind that infiltrates to get close to the intended target. That uses subterfuge and deception to remain hidden until they can act.

You can refluff the magic bits so they're less magical: make it a psychological effect (Words of Terror) or just a high expertise in disguises (Mantle of Whispers).

To me, an assassin has 2 important elements: being able to strike hard and true, yes, but also the means to get close to their target and learn their weaknesses without being noticed. That latter element is imho even the most important one, as it marks the difference between an assassin and just a skilled murderer.