Building the Ultimate Shadow Monk Ninja Assassin...

[igor140]

I know this concept has been done and redone and discussed 1007 times, but I cannot find any that directly discuss it in light of Xanathar (i.e., Gloom Stalker).

So, the crux of what I'm trying to build is Shadow Monk 6, as that gives Shadow Step and enough ki points to get some stuff done. And this is where it starts getting complicated.

Ranger (Gloom Stalker) 3 seems to be enough, and also to be amazing. I realize Dread Ambusher is only in effect for the first round of combat, but Ranger also gives some other really good stuff: Hunter's Mark and Zephyr Strike, better skill and equipment proficiencies, and Favored Enemy (which is why I would probably start as Ranger). The only reason I can see going more than 3 levels in Ranger is for the ASI (or possibly feat, considering he won't be very MAD).

Then there's Warlock... I've got a lvl 10 Warlock in a different campaign right now, and he's AMAZING. The advantage of this for the Shadow Monk build is the obvious Devil's Sight and the fact that Eldritch Blast is generally useful... but so is the bow I would get from Ranger (or Rogue, for that matter). So Warlock doesn't really seem worth the dip just for the one invocation when I can probably justify the same effect from Umbral Sight. Also, the CHA dependency complicates things...

And then it makes the most sense to round things out (though not necessarily in this order) with Rogue. Both Monk 7 and Rogue 7 give the same AoE dodging ability, but I see more value in taking Rogue higher than Monk.

Above Monk 7, I would get
11: Cloak of Shadows (nice, but somewhat redundant as compared to expertise in Stealth)
13: Tongue of Sun and Moon (REALLY cool, but I'll already have TONS of languages between Ranger, Rogue, and background)
14: Diamond Soul (also very cool, but it seems hard to justify hanging around this long in this class)
17: Opportunist at 17 (VERY nice, but doesn't seem worth hanging around another 10 levels for...)

Conversely, above Rogue 7, I would get
10: Bonus ASI (very helpful for all those nifty feats)
11: Reliable Talent (does this seriously mean you can NEVER crit-fail a check again? regardless, with all the proficiencies Rogues get, this is AMAZING)
11: 6d6 Sneak Attack
(14): Blindsense (I guess I could forego Ranger altogether and never have to worry about Darkness teleporting again... but I like Gloom Stalker)

So, I'm currently thinking Ranger (GS) 3/ Monk (WoS) 6/ Rogue (Ass) 11... in some order or another.

Related to this, does the "surprise" aspect of Assassinate relate to ALL attacks done on the "surprise" round, or just the initial one? Because at lvl 20, that would be
6d6 (attack + extra attack + Dread Ambush with shortsword, all guaranteed critical) +
4d6 (Flurry of Blows, both critical) +
1d8 (Dread Ambush) +
12d6 (Sneak Attack, all guaranteed critical) +
20 (five distinct attacks against Favored Enemy with Dueling)

... all before considering magical weapons. And all of those attacks are made with advantage. For those not counting it out, that an average of 101.5 points of damage (160 max)... and THEN the turn order begins.

But wait! There's more! The first few levels of EACH of those classes provides so much utility that this dude would still have a lot to do in non-dungeon, RPing sections.

The only downside I see (and this is a pretty significant one) is that where most characters "mature" around lvl 13, or dual-class into something builds on an existing strength, this one really needs around 18 levels to come into his own... but he's still useful in the meantime.

SO! Is there a more efficient/ more powerful way of doing this? Are my calculations correct? I realize I could make an assassin that DOOS MOAR DMGGGG!!!, but I like the flexibility, utility, defenses, and badassery of the core concept: he appears out of the shadows, kills two people, and is gone again.

Anyway, thoughts?

[HPisBS]

This was almost exactly my thoughts when I first saw the Gloom Stalker, and I've recently been playing with the idea again.

I'm pretty that sure surprised lasts until the end of the round. In which case, the math for that level 12 ambush could actually be:
2 x (3d6 regular attacks + 2d6 Flurry of Blows + 2d6 sneak attack + 5d6 Hunter's Mark + 1d8 Dread Ambusher) + 25 dex → 24d6+2d8+25 = ~118.

That should be enough to drop a fighter of similar level. It may even take out a lvl 12 barbarian! (12 first lvl +11d12[~77]+36 con = 125 hp). And even if it wasn't enough, he very well may wind up stunned anyway.

But of course, that's only if you manage to catch your target by surprise. Granted, between your expertise in stealth as a rogue, Pass Without Trace as a shadow monk, and invisibility in darkness as a gloom stalker ranger, you have a lot to help you set that up. Even so, it's still not going to apply to most encounters – like those that happen in broad daylight while walking down the road with your party.

Sadly, as absolutely awesome as this concept is, it's so niche that it works better for a solo character... like an npc the villain hires to deal with the pesky adventures who keep getting in the way. (Think how much tension there'd be at the table if a dark figure suddenly dropped down behind your party's lookout, covering his mouth and stabbing him again and again. Initially, he takes ~ 33 damage, but then he's hit again for another ~ 19 damage. And then for another ~ 28 damage. And another 19. And another. So by the end, the lookout's taken somewhere around 118 damage – enough to drop him. Think of how nervous everyone would be when the only lookout is making death saves... and the rest of the party's still asleep!



Since, like I said, a PC will likely be unable to surprise most enemies while travelling with a party, I think the more prudent – though far less flavorful – one-turn-kill build may be Rogue 4 / Hexblade Warlock (chain pact) 3 / Battle Master Fighter 5.

Hexblade 3 gets you Hexblade's Curse (+ prof bonus to damage, and crit on 19s), as well as invocations and 2nd tier spells – which lets you choose between standard Hex, Darkness shenanigans, and Shadow Blade (which works with sneak attack, but 2d8 psychic/hit). Meanwhile, Pact of the Chain means you can always have a flying scout helping you know when and where you need to set up your ambushes.

Battle Master 5 gets you your 2 base attacks + action surge + maneuvers. This is where and how damage actually manages to surpass even our true ninja's assassination.
Action surge gets us our 4 attacks in one round. Maneuvers add an extra d8 each attack (up to 4 times / rest, or 5 if we take Martial Adept). Put it all together, and the Hexblade Assassin Master can ambush a little more often for:
2 x (8d8 Shadow Blade + 4d8 maneuvers + 2d6 sneak attack) + 20 dex + 16 hexblade curse → 24d8 + 4d6 + 36 = ~ 158 psychic.
- Alternatively, 2 x (4d8 longbow + 4d8 maneuvers + 2d6 sneak attack + 4d6 hex) + 36 = ~ 150 ranged piercing / necrotic.


If you nova w/out surprise, then it drops to ~ 88 psychic.

Ether way, this nova uses up all but one of your /rest resources. Subsequent rounds would only get you 4d8+2d6 + 10 = ~ 35 psychic dmg (or 60 if you ambush someone else before resting).

So while this Hex-Master-Assassin build deals more damage (and is potentially better at setting it up thanks to the chain pact), it is very nova, making the true ninja / Shadow-Stalker-Assassin we both initially thought of fare better over multiple rounds with ~ 55 non-surprise damage. (ShadowStalker is also much better at escaping after the initial assassination, thanks to Shadow Step & Umbral Sight.)


...
That said, I guess the only question that really remains is: Which is better for setting up those ambushes? Pact of the Chain for advanced scouting, or Pass Without Trace + Umbral Sight (along w/ Shadow Step and Dread Ambusher's initiative bonus)?


Edit Either way, Elven Accuracy feat gives turns your advantage into super advantage, so you'd definitely want to work that in if you can. ... Too bad this is already MAD, yet short on ASIs lol

[djreynolds]

In the guide section is the death dealer's handbook.

Shadow monk, warlock, battlemaster, assassin and now gloomstalker.

Very ninja

[Keravath]

One thing to keep in mind ... casting hunter's mark is a bonus action, using flurry of blows is a bonus action, sneak attack requires the use of a finesse monk weapon which pretty much means a short sword I think. If you get surprise as an assassin, all your attacks which hit targets that have not had their turn in initiative order are criticals. Even without surprise, the assassin ability provides advantage in the first round against creatures that haven't had their turn yet.

Also keep in mind that dueling applies to the melee weapon attacks and not the monk unarmed strikes. Favored enemy damage is UA though if your DM allows it then no worries.

Anyway, it can be a solid single target damage build. However, the level 14 monk ability diamond soul is amazing at higher levels. The extra ki is also very very useful. So another build option might be 3 Gloomstalker/17 monk depending on what you want to get out of it (or 3 gloomstalker/3 rogue/14 monk but that sacrifices a lot of ASIs for a build that needs them)

[HPisBS]

One thing to keep in mind ... casting hunter's mark is a bonus action, using flurry of blows is a bonus action, sneak attack requires the use of a finesse monk weapon which pretty much means a short sword I think.

If you're going to ambush, then just cast on the turn before you attack. As for the weapon, notice my math used d6's for all the ShadowStalker's attacks. As a lvl 6 monk, that can mean short sword or even a dagger. (of Venom, perhaps?)