I've been chewing on the idea of a triple class Shadow Assassin using Monk as my main and dipping into warlock and rogue. Monk obviously for the shadow monk abilities, warlock as secondary for the blade pact and 3 invocations devil sight, mask of many faces, and thirsting blade. Then rogue for the assassin perks with atleast the chance to get one insta kill using the surprise crit.
So by the time i hit level 14 my class will function how id want it to. Using shadowstep i teleport behind an enemy and assassinate them and with thirsting blade id get two attacks with my pact blade potentially killing two people at once if the assassinate skill stacks like that. I'd have to know the exact ruling i guess if two enemies are close enough and I use that combo could i potentially kill them both using thirsting blades double attack and have the surprise crit on both attacks.
Also id use the warlocks spell casting on illusion and enchantment spells to set up a nice ambiance before the attack or just for fun.
The levels by 14 would be monk 6, warlock 5, rogue 3 and then just dump the rest into monk till max level.
Thirsting Blade and Extra Attack do not stack. Since you will be getting EA from Monk already, don't bother wasting an invocation on Thirsting Blade. It is literally a waste. Really, the only things you'd get out of Warlock that will be useful are the Devil's Sight & Mask of Many Faces invocations, and Hexblade's Curse (except not really, detailed below).
Assassinate only works on creatures that are surprised, but it can work on multiple surprised creatures. If the creatures are not surprised, then the only benefit you gain from Assassinate is advantage on the attack, and that is also only against creatures that have not taken a turn yet.
Sneak attack is limited to one use per turn. You cannot sneak attack two targets in the same turn even if both attacks are eligible for the bonuses from Assassinate. That's not usually a deal-breaker by itself, but you need to know that since you're designing your character's features to be heavily front-loaded.
You will also be restricted to using a Dagger or Shortsword as you must be using a Finesse weapon. Unarmed strikes do not qualify. You already mentioned using a blade, so just pointing this out for clarity's sake.
I don't think you should take any levels in Warlock at all, but don't bother going past level 2 if you do. Don't bother with Hexblade either. You want to pump up Dex as much as possible even if you could use Charisma as your attack stat... so don't bother... Monk is already MAD enough as is. You will get no benefit from Hex Warrior. Hexblade's curse could be beneficial... except you already have plenty of things that compete for that bonus action slot... like Martial Arts bonus actions. You will get more out of that than the +proficiency bonus damage. The expanded critical range is pointless if you're focusing on assassinating. The advantage granted from Darkness is also negated by Assassinate. These are things that are most beneficial when you start an encounter by using them, so either you forgo the benefits of Assassinate in your first round, or you waste a round using them later for significantly reduced benefit.
TL;DR don't bother with Warlock at all for your goal. If you still want to, don't go past level 2 Warlock, and pick a different patron from Hexblade.
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You don't know what fear is until you've witnessed a drunk bird divebombing you while carrying a screaming Kobold throwing fire anywhere and everywhere.
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I've been chewing on the idea of a triple class Shadow Assassin using Monk as my main and dipping into warlock and rogue. Monk obviously for the shadow monk abilities, warlock as secondary for the blade pact and 3 invocations devil sight, mask of many faces, and thirsting blade. Then rogue for the assassin perks with atleast the chance to get one insta kill using the surprise crit.
So by the time i hit level 14 my class will function how id want it to. Using shadowstep i teleport behind an enemy and assassinate them and with thirsting blade id get two attacks with my pact blade potentially killing two people at once if the assassinate skill stacks like that. I'd have to know the exact ruling i guess if two enemies are close enough and I use that combo could i potentially kill them both using thirsting blades double attack and have the surprise crit on both attacks.
Also id use the warlocks spell casting on illusion and enchantment spells to set up a nice ambiance before the attack or just for fun.
The levels by 14 would be monk 6, warlock 5, rogue 3 and then just dump the rest into monk till max level.
Thirsting Blade and Extra Attack do not stack. Since you will be getting EA from Monk already, don't bother wasting an invocation on Thirsting Blade. It is literally a waste. Really, the only things you'd get out of Warlock that will be useful are the Devil's Sight & Mask of Many Faces invocations, and Hexblade's Curse (except not really, detailed below).
Assassinate only works on creatures that are surprised, but it can work on multiple surprised creatures. If the creatures are not surprised, then the only benefit you gain from Assassinate is advantage on the attack, and that is also only against creatures that have not taken a turn yet.
Sneak attack is limited to one use per turn. You cannot sneak attack two targets in the same turn even if both attacks are eligible for the bonuses from Assassinate. That's not usually a deal-breaker by itself, but you need to know that since you're designing your character's features to be heavily front-loaded.
You will also be restricted to using a Dagger or Shortsword as you must be using a Finesse weapon. Unarmed strikes do not qualify. You already mentioned using a blade, so just pointing this out for clarity's sake.
I don't think you should take any levels in Warlock at all, but don't bother going past level 2 if you do. Don't bother with Hexblade either. You want to pump up Dex as much as possible even if you could use Charisma as your attack stat... so don't bother... Monk is already MAD enough as is. You will get no benefit from Hex Warrior. Hexblade's curse could be beneficial... except you already have plenty of things that compete for that bonus action slot... like Martial Arts bonus actions. You will get more out of that than the +proficiency bonus damage. The expanded critical range is pointless if you're focusing on assassinating. The advantage granted from Darkness is also negated by Assassinate. These are things that are most beneficial when you start an encounter by using them, so either you forgo the benefits of Assassinate in your first round, or you waste a round using them later for significantly reduced benefit.
TL;DR don't bother with Warlock at all for your goal. If you still want to, don't go past level 2 Warlock, and pick a different patron from Hexblade.
You don't know what fear is until you've witnessed a drunk bird divebombing you while carrying a screaming Kobold throwing fire anywhere and everywhere.