What The Best Background For An Assassination Rogue

The pocketknife in the dark… The faceless killer… The death you lot never saw coming. Rogues are a surprisingly versatile form, with a diverse toolkit that tin can brand them dexterous trap breakers, silent scouts, and, of class, devastating single-target damage dealers.

The Assassin subclass takes the Rogue'southward infiltration and single-target impairment abilities and hones them to a razor'south edge.

Welcome to our guide to the Assassinator Rogue. Our goal with this serial of subclass guides is to give yous a scannable, comprehensive introduction to playing different character builds in Dungeons & Dragons 5e.

We'll offset off this guide by breaking downwardly what sets the Assassin apart from other classes and roguish archetypes – its strengths, and some of the weaknesses you'll demand to exist aware of and compensate for if you want to play an Assassin to the fullest.

We'll too look at a few of the potential options for multiclassing an Assassin that help accentuate its strengths and compensate for its weaknesses.

Then, we're going to go into detail apropos how to build an Assassinator from 1st level, breaking downwardly which Ability Scores to prioritize, also as the best races, backgrounds, and skills to help round out this build, including some suggestions Feats that can aid bring out the best in the subclass.

Once we've covered grapheme cosmos, we'll wait at the unique features that ascertain the Assassin every bit you level up from 1st to 20th level, besides as present yous with an instance build to assistance you brand your own dealer of death.

Black Citadel's Ranking and Tier System

In our ongoing serial of 5e course guides, we use the following color rating scheme:

Crimson – C Tier. Red options can sometimes be situationally useful, and might make for an interesting narrative pick, but are largely less effective than other tiers.

Green – B Tier. A solid choice, but nothing that is absolutely critical for a build, or can be very good but just situationally.

Blue – A Tier. An excellent choice. Widely regarded equally powerful in some way, useful, highly effective.

Purple – Southward Tier. The best of the all-time. Objectively powerful or transformative in some way. No choice in D&D is essential, but these options are definitely worth considering when you create your character.

Our goal here is to provide scannable, but comprehensive guides for you equally you lot develop your character.

What is an Assassin Rogue?

Want to play a master burglar who can walk right into a heavily-guarded room and bury a knife in their target'due south heart? An unstoppable compensation hunter? The ultimate spy? The Assassin is the subclass for you.

In many means, the Assassin distils and simplifies the Rogue, taking a class that can – with the correct build – do a little bit of everything, from combat to scouting to burglary to social situations, and condenses it downwards to 2 things: infiltration and assassination.

You lot are going to end up doing those two things very, very well, but at the expense of the broad utility skillset other roguish archetypes similar the Thief or the Arcane Trickster relish.

Because of how hyper-focused the Assassin is in terms of mechanics, they can be ane of the easiest roguish archetypes to play for beginners – somewhat akin to the Champion Fighter or the Light Domain Cleric, the Assassin does what it says on the tin simply, elegantly, and doesn't do much else.

The Assassinator'due south Defining Abilities

Lethal impairment when you get the drop on enemies
Master infiltrator
Capable poisoner

The Assassin is all about getting the drop on your enemies. If the bad guys surprise you, see you coming, and get to act outset, and then a lot of your impairment disappears into sparse air. And so, brand sure you lot get the drop on your opponents.

Your Assassinate ability comes online at 3rd level, and ensures that you lot take advantage on any set on you brand confronting a creature who hasn't acted already in combat on the same turn.

Also, whatever successful assail you lot brand confronting an enemy who is surprised is automatically a critical hit. This stacks amazingly well with your Sneak Set on feature – which grants you an extra d6 of harm on a damage roll with a ranged or finesse weapon once per turn, and grows in power every bit you level upward to the point where you lot can deal an extra 10d6 damage per round when you lot hit 20th level.

Land a surprise blow with your Electrocute characteristic and that Sneak Attack harm becomes 20d6 at 20th level.

Then, once you unlock your Death Strike ability at 17th level, whatsoever surprised creature yous hit by an attack must pass a Constitution saving throw or take double damage from your attack.

That means that you lot're applying your weapon harm plus your Dexterity modifier plus 20d6 of Sneak Attack impairment times two as part of your surprise round.

This ways that gaining a surprise round, followed by a nifty initiative coil, can drastically affect your usefulness in combat.

The other edge to the Assassinator's bract is the classic'southward ability as an burglar.

Rangers might exist skilful at passing without a trace through the wilds, and the Scout Rogue might exist the class' best all-round stealth-focused subclass, but no i tin outfox an Assassin when it comes to getting past guards, moving unseen in a crowd, and stealing the face up of another to do information technology.

When you lot choose the Assassin at 3rd level, you lot immediately proceeds proficiency with the disguise kit, which is useful in of itself. And then, one time you lot reach 9th level things start to go really sneaky.

Your Infiltration Expertise lets you spend a calendar week and 25gp creating a faux identity for yourself. Establish yourself as a wealthy merchant looking to build a granary nearby to gain an audience with the local lord.

Spread rumors well-nigh your desire to purchase a sure cursed antiquity, along with the information that you lot have the money to pay for it; accept on the guise of a apprehensive servant of a local goddess, harmless enough to pass through the city without alluring the attentions of the local watch.

Yous can't steal someone else's identity until 13th level, when your Impostor ability lets you unerringly mimic someone's spoken language, writing, and behavior.

Once you're close to your target, yous tin too use your proficiency with the poisoner's kit to arts and crafts undetectable killing draughts, or paralytics to lace the edge of your blade.

The mixture of infiltration skills and vicious damage output makes the Assassinator capable of being a very subtle character well-suited to campaigns rife with political intrigue and social duelling, while as well being one of the about potent harm dealers in the game – striking from the shadows to erase their enemies from beingness earlier melting dorsum into the darkness.

I retrieve this is one of the best classes in 5e when it comes down to mechanically recreating the idea I take in my head of existence a spy or assassin – a la James Bond, Agent 47, or Jaqen H'ghar.

The Assassinator's Limitations

Lacks versatility
Infiltration skills can often fall by the wayside in combat-focused campaigns
Highly dependent on good initiative rolls

That being said, any bracket that focuses on being very, very good at merely a few things is inevitably going to cease up being quite bad at only about everything else.

Kickoff of all, when it comes to defense, support, utility, exploration, disarming traps, and when it comes to just about anything that doesn't fall within the sphere of either ambushing your enemies or infiltrating social situations, this subclass isn't going to do much for you.

That doesn't brand y'all weak by any means, and you're likely to accept political party members who can compensate for your shortcomings, but if you like to be the player who has something for every state of affairs, then you might struggle. If you similar to be the best in a few situations, however, you're in the right identify.

Also, when it comes to the things that you lot're actually good at, there's a schism between Assassinate (3rd) and Death Strike (17th), and Infiltration Expertise (9th) and Imposter (13th). The former pair emphasize pretty constant combat, whereas the middle two abilities push you towards more than of a roleplaying-focused playstyle.

That means that, if yous're playing in a entrada that's all nigh courtly intrigue and veiled threats made while strolling through perfectly manicured gardens, and so your third and 17th level abilities are going to feel a lilliputian useless.

If you're playing a classic dungeon crawl entrada (the more than likely scenario) that involves walking to a big hole in the footing, murdering everything inside it, and figuring out how to haul anything shiny dorsum to boondocks to sell, then the ability to convince the goblins living in the big hole that you're really Morton the Accountant who likes to beg big on the ponies probably isn't going to do much for you lot.

Manifestly, no campaign is costless from social situations or combat, but the Assassin (much like James Bail, glibly murdering foreigners in between turns at the baccarat table) does best when there are opportunities for both.

When the knives do come out, you lot're also going to want to take corking intendance to endeavor and get the drop on your opponents. A surprise circular can let y'all deal a shocking corporeality of harm to a single enemy before the fight has even begun.

And so, in one case it'due south time to roll initiative, a low score can make the difference between successfully landing a killing blow every round and missing half of your attacks. Make certain your initiative is as loftier as possible.

The Weapon of Warning

I wouldn't e'er dream of saying a subclass doesn't piece of work without a specific magic item, just for the Assassin a Weapon of Warning is pretty close to essential gear.

You lot can read our full guide to the Weapon of Warning here, but substantially information technology gives you (and your allies) reward on initiative rolls and ensures you can't exist surprised. In the hands of an Assassin, this might be the nearly useful pairing of equipment and class features I've seen anywhere in D&D.

Multiclassing

With a subclass every bit specialized as the Assassin, multiclassing can be a great way to either compensate for its shortcomings or double downwardly on the things information technology does best. The Gloomstalker Ranger requires you to take iii levels outside of Rogue.

The Oath of Vengeance Paladin and the Grave Domain Cleric only require ii levels, although taking more levels of Grave Domain can give yous a potent boost to your spellcasting.

Gloom Stalker Ranger

The Gloom Stalker is easily the almost roguish path for a Ranger, and its features synergize beautifully with the Assassinator. Y'all get access to the disguise self spell, which complements your infiltration abilities, only it'south your Dread Ambusher and Umbral Sight features that really gel with the Assassinator.

Dream Ambusher gives you a boost to your initiative rolls, equally well as an extra attack with a juicy 1d8 of bonus damage on the first round of combat. Umbral Sight not merely buffs your darkvision, but helps yous stay hidden from creatures that can run into in darkness and depression light.

Grave Domain Cleric

Grave Domain Clerics are all about death and darkness – a perfect thematic fit for an Assassinator in service to a cult or religious lodge of killers. You also proceeds access to some useful spells to round out your utility and your Channel Divinity pick Path of the Grave lets you inflict double damage on a target for a whole circular.

Combine that with your already fearsome Sneak Attack and Assassinate Damage (and once more later on with Death Strike) and you tin easily dish out more than 200 damage on the commencement round of combat.

Oath of Vengeance Paladin

Dexterity-based Paladin builds are hugely underrated, and the fact that the Assassin is basically a single ability-dependent subclass means you'll take some actress points to sprinkle into Charisma without compromising your other vital abilities besides badly.

Any graphic symbol with the power to crit ofttimes is a keen fit for a Paladin multiclass, because your Divine Smite's harm dice are also doubled. The Oath of Vengeance takes everything useful almost the Paladin and dials information technology up to 11: you get admission to spells similar Bane and Hunter's Mark, and your Vow of Enmity is another smashing way to get even more advantage on a single target.

Ability Scores

Primary: Dexterity

Tier Two: Constitution, Charisma

Tier Three: Intelligence, Wisdom

Absolute Dump Tier: Strength

Force: Nearly completely useless. Skip it. Anything higher than 10 is basically a waste.

Dexterity: When y'all sit down downwardly to build an Assassin, your first (and, unless you're planning on multiclassing, last) business concern is going to be a high Dexterity score. You're going to be wearing calorie-free armor, so your Dexterity is going to determine your AC. You're going to exist using ranged or finesse weapons, then your Dexterity is going to link to your harm. And you lot're going to be directly relying on your Dexterity to have a high initiative bonus, which is linked to the bulk of your damage output. Get this to xx every bit before long as you lot possibly tin can.

Constitution: More than hit points are, equally always, never a bad affair – especially for a class that thrives on flight solo.

Intelligence: Useful for Insight checks and possibly some flavor skills like History or Arcana, but unless it's part of your graphic symbol concept, you can skip a high Intelligence score.

Wisdom: Useful for Perception checks to go the drop on enemies, but otherwise not-essential.

Charisma: Yous're actually rather well equipped to serve as the party's face up, and then a high Charisma score can terminate up being useful if you're trying to trick and talk your style past the palace guards.

Races

Equally nosotros've established in a higher place, we're going to be prioritizing Dexterity, Charisma, and Constitution, and then any races that give united states of america a bonus in those departments are a skilful start. Then, any races that give us some skilful abilities or admission to Feats are going to aid whittle down those choices.

The rules for the Wood Elf and Variant Homo are constitute in the Player'due south Handbook. The rules for the Tabaxi are from Volo'southward Guide to Monsters.

Woods Elf

All elves go a prissy +2 bonus to Dexterity to start things off, significant you can begin with sixteen Dexterity at 1st level and have twenty by 8th. You get Perception proficiency, darkvision, and advantage on saves confronting existence charmed.

All practiced stuff. Forest Elves also become a useful +1 to their Wisdom, faster walking speed, and the ability to use Mask of the Wild to hide, even when lightly obscured by foliage, heavy pelting, falling snow, mist, and other natural phenomena – a great point of synergy with your Cunning Action.

Variant Human being

I pretty much always recommend the Variant Human being no matter the grade I'm writing a guide for because they tin can kind of do it all. You get a +1 bonus to two ability scores of your choice (go for Dexterity and something else, which is great if you're planning to multiclass later), a skill proficiency of your choice, and a Feat at 1st level which is amazing.

I would wholeheartedly recommend Alert as a mode to further boost your Initiative to ensure you're practically guaranteed to get reward on your attacks.

Tabaxi

Everything about Tabaxi (D&D's resident cat people) screams Rogue, and they're especially suited to being Assassins. You get a +2 to Dexterity and a +1 to Charisma, which complements your abilities perfectly.

You lot also get a boost to your move speed, a dandy climbing speed, proficiency in Perception and Stealth, and darkvision. A great choice all circular.

Backgrounds

Backgrounds are both a great way to assistance flesh out your character's personal history, and your primary source of skills.

Each background besides has its own special feature – something which I maintain remains a woefully underused aspect of D&D; take the Criminal'southward natural power to describe upon a network of contacts for information, leads and jobs, or the fact that the Sage'southward Researcher feature means that, even if they can't recall a slice of lore, they know exactly where to go to get it.

Background features are a fantastic way to make your character feel competent within the environment in which they live, as well equally help the DM mankind out the world around y'all.

As an Assassin, your groundwork can exist a great fashion to effigy out what kind of killer you are – sworn to the service of a guild, the renegade ex-cultist of a death god, or an international woman of mystery.

The Acolyte tin can be a great source of flavor if you're looking to play an initiate raised in service to some dark cult or guild of mystics. You get Insight and Religion proficiency – neither are perfectly optimal but Religion is one of the few skills the Rogue doesn't get access to right out of the gate.

Also, y'all gain access to shelter and healing from those who share your religion.

The Criminal/Spy background as well fits perfectly with an Assassin. You lot gain some useful equipment, proficiency in Deception and Stealth, and access to a network of underworld contacts.

Or, if you prefer to go all-in on the very Game of Thrones intrigue-focused playstyle, the Courtier gives y'all proficiency in Insight and Persuasion, besides as some actress languages, and the ability to have your finger on the pulse of whatever noble intrigues are affecting the local area.

Cull this if your entrada is likely to go political, or yous desire to fully footstep into the part of the party's face.

Skills

The Rogue's starting skill list is pretty fantastic. You lot get to cull four skills from Acrobatics, Athletics, Deception, Insight, Intimidation, Investigation, Perception, Performance, Persuasion, Sleight of Hand, and Stealth at 1st level, which is fantastic. Only Bards are better skill monkeys.

Combined with your groundwork and any proficiencies granted by your race and you could start the game with proficiency in upwards to viii skills, which can become a long way towards compensating for the Assassinator's somewhat singular focus on stabbing and sneaking.

Choosing skills can depend on your political party composition (there'due south no sense picking upwardly Arcana if you already have a Sorcerer and a Knowledge Bard in your group, for example) but the roguish ones are never a bad bet.

Principal: Sleight of Hand, Stealth, Deception, Perception

Tier Two: Acrobatics, Investigation, Persuasion,

Tier Three: History, Religion, Intimidation, Performance, Survival

Absolute Dump Tier: Athletics, Arcana, Nature, Medicine, Creature Handling

Feats

Feats can exist a swell way to circular out or broaden your character'due south abilities. If Feats are something you're interested in taking, try playing a Variant Human or any race using the Custom Lineage optional rules from Tasha'south Cauldron of Everything.

Alert: Gaining a +5 bonus to your initiative rolls would be worth taking this Feat by itself, given how important existence high in the club is to an Assassinator. However, you also cannot be surprised while conscious, and other creatures don't become advantage on attacks made against you every bit a result of being unseen.

Sharpshooter: A fantastic pick if you want to be a ranged Assassinator. Also, the advantage you get on a surprise round synergizes perfectly with the Sharpshooter'south ability to take a -five penalty to hit in exchange for 10 extra damage. Y'all can also hit enemies from range with ease and ignore half and three-quarters cover.

Piercer: Perfect for a Rogue using a rapier or a ranged weapon, peculiarly as yous don't get the multiple attacks per circular that other martial classes enjoy. This Feat lets you lot reroll damage from a piercing attack once per round and use the new result. You lot also get a nice little +1 bonus to your Strength or Dexterity.

Poisoner: Although y'all already take proficiency with the Poisoner's Kit, the fact that this Feat lets y'all arts and crafts poisons in an hour, every bit opposed to over an extended catamenia of downtime, is a great way to flesh out your Assassin's toolkit.

Yous can spend an hour and 50gp worth of materials to create a number of doses of toxicant equal to your proficiency bonus. You can then coat your weapons with this poison, which remains effective for an hr and forces any enemy to brand a DC xiv Constitution saving throw or have 2d8 harm and be briefly poisoned.

Progression

Let'south accept a wait at the unique features that take an Assassinator from 1st level to 20th. Note that this guide won't exist roofing the class features bachelor to all Rogues like Cunning Activity, Expertise, and Sneak Assault in particular.

1st & 2nd Level

Until you choose your roguish classic at third level, you're going to be playing a bog standard Rogue. Your hit dice is a d8, your saving throws are in Dexterity and Intelligence, y'all tin can speak, read and write Thieves' Deceit, and you become a huge pile of skills from which yous tin can pick four in conjunction with those offered up past your background and race.

You also get Expertise (which allows you to double your proficiency bonus either with 2 skills or one skill and your Thieves' tools.

And you lot get Sneak Assail at 1st level, which lets you deal some extra impairment once per turn to a target that's either incapacitated or within 5ft of one of your allies, or if you have advantage on the set on whorl.

At 2nd level you proceeds Cunning Action, which lets you use your bonus action to hide, disengage, or dash, making you more than capable of slipping in and out of danger with ease.

3rd Level

When you hitting 3rd level, you tin can select the Assassin roguish archetype. Yous gain the post-obit…

Bonus Proficiencies: You gain proficiency with the disguise kit and the poisoner's kit, although yous don't gain the physical kits themselves; you lot'll need to source them from somewhere else.

Assassinate: You become a chief of striking down foes before they have a chance to act. You gain advantage on attack rolls against a animal that hasn't taken a turn in combat yet, making a high initiative bonus a critically high priority. Likewise, if you hit an enemy that is surprised, the hit automatically becomes a critical.

9th Level

Infiltration Expertise : You lot gain the ability to fabricate a near-perfect imitation identity for yourself. Y'all spend a week and 25gp to establish the history, profession, and affiliations of your alias – and yous tin can't steal someone else'south identity.

13th Level

Impostor : This is where the identity theft begins in earnest. You proceeds the ability to "unerringly mimic" the speech, writing, and behavior of another person. You must spend three hours studying the private yous will be impersonating, afterwards which you will take absorbed their mannerisms and behavioral quirks perfectly.

Your ruse is completely unnoticeable to the casual observer, and if a wary creature wants to probe for the truth, you take reward on whatever deception check made to conceal your true identity.

17th Level

Decease Strike : You are at present a master of the one-hit impale. When you hit an enemy that is surprised with a weapon set on, yous force it to make a Constitution saving throw. The DC is 8 + your proficiency bonus + your Dexterity modifier.

If the target fails, you inflict double damage on the target, including from your Sneak Attack, a critical striking, and any other sources of actress injure. This ability lets you first doling out truly stupid amounts of harm if you get the jump on someone.

Example Assassin Build Progression from 1st to 20th Level

If you want to aqueduct the suave, subtle, sophisticated, and ruthlessly mortiferous way of famous assassins like James Bail, the Jackal, or John Wick, then follow this listing of steps to take your very own killer from 1st to 20th level.

1st level

Ability Scores (Standard Array): Forcefulness (eight), Dexterity (xv), Constitution (12), Intelligence (x), Wisdom (14), Charisma (thirteen).

Race: Tabaxi

Ability Score Increment: Dexterity +2 (17), Charisma +1 (14)

Size: Medium

Speed: 30ft

Darkvision: Yous have a cat'southward keen senses, especially in the dark. You can see in dim light within 60 feet of y'all equally if it were bright light, and in darkness as if it were dim light. You tin can't discern color in darkness, only shades of gray.

Feline Agility: Your reflexes and agility permit you to move with a burst of speed. When you move on your stomach in combat, you can double your speed until the end of the tum. Once you use this trait, yous can't use it over again until y'all motion 0 feet on one of your turns.

Cat'southward Claws: Because of your claws, you have a climbing speed of 20 feet. In add-on, your claws are natural weapons, which you lot tin can use to brand unarmed strikes. If you hit with them, y'all bargain slashing impairment equal to 1d4 + your Force modifier, instead of the bludgeoning impairment normal for an unarmed strike.

Cat'southward Talent: You accept proficiency in the Perception and Stealth skills.

Languages: Mutual, Undercommon (race)

Proficiencies

Armor: Light armor

Weapons: Simple weapons, hand crossbows, longswords, rapiers, shortswords

Tools: Thieves' tools, Playing Cards (gaming set)

Saving Throws: Dexterity, Intelligence

Background: Courtier

Skills: Perception, Stealth (race), Insight, Persuasion (background), Acrobatics, Deception, Investigation, Sleight of Hand.

Expertise: Deception, Stealth

Hit Points

Hit Dice: 1d8 per rogue level

Hit Points at 1st Level: 8 + your Constitution modifier

Hit Points at Higher Levels: 1d8 (or v) + your Constitution modifier per rogue level after 1st

Equipment

Rapier (1d8 piercing harm, finesse)
Two daggers (1d4 piercing, finesse, low-cal, range, thrown)
Leather Armor (light, AC 11 + Dexterity)
Shortbow (1d6 piercing, ranged, lite), xx arrows
Burglar's pack
Crowbar,
Dark common clothes including a hood
15 gp

Sneak Attack : 1d6

Thieves' Deceit

2d level

Cunning Activeness

3rd level

Roguish Archetype: Assassin

Assassinate

Bonus Proficiencies: Disguise Kit, Toolkit

Sneak Set on: 2d6

fourth level

Feat: Piercer, +one Dexterity (18)

fifth level

Uncanny Dodge

Sneak Attack: 3d6

6th level

Expertise: Perception, Acrobatics

seventh level

Evasion

Sneak Attack: 4d6

8th level

Feat: Alert

9th level

Infiltration Expertise

Sneak Assault: 5d6

10th level

Ability Score Improvement: +2 Dexterity (20)

11th level

Reliable Talent

Sneak Assail: 6d6

12th level

Ability Score Improvement: +2 Charisma (16)

13th level

Impostor

Sneak Attack: 7d6

14th level

Blindsense

15th level

Slippery Mind

Sneak Attack: 8d6

16th level

Power Score Improvement: +2 Wisdom (16)

17th level

Death Strike

Sneak Attack: 9d6

18th level

Elusive

19th level

Ability Score Comeback: +ii Charisma (18)

Sneak Attack: 10d6

20th level

Stroke of Luck

A Beginner's Guide to Playing an Assassin

If the Hitman games (or mayhap the commencement level James Bond 007: Nightfire) take taught us anything, it's that playing an assassin is really fun.

Scouting out your target, infiltrating the perimeter, using your skills of deception or suave amuse to gain access to an elegant garden party or high stakes poker game – all leading up to the moment when your target is alone, defenseless – it's an incredibly satisfying gameplay experience.

While porting James Bail or Jason Bourne into the earth of D&D might seem like a bit of a tonal clash, it's an idea that gets cooler the more I think nearly it.

The thought of playing a character that excels at gaining admission to restricted areas and taking down their target before they have a chance to human activity is an undeniably evocative 1. If playing 007 in the Forgotten Realms sounds like a good fourth dimension to yous, the Assassinator roguish archetype is definitely the mode to do it.

It's a subclass that thrives on using false identities, clever disguises, and bluff trickery to go shut to the bad guys, and a brutally effective set of skills to brand certain they never make it out alive.

In fact, when the conditions are right, I'yard not sure there's another class in D&D 5e that is as constructive every bit the Assassin when it comes to dealing single-target damage in i, hyperconcentrated burst.

Past the time you lot hit 20th level, your Sneak Assault ability means that you can add a full 10d6 damage to a weapon assault once per plow (provided you lot have reward or the target is continuing within 5ft of 1 of your allies, etc, etc.).

Combine that with your Assassinate ability (which means you have advantage on any enemy that acts after you in the initiative order, and ensures that any hit confronting a surprised enemy is automatically a disquisitional, and you lot can terminate upwards rolling 20d6 of sneak attack damage on a crit.

Then, apply your Decease Strike ability (which forces whatever surprised enemy to make a Constitution relieve or take double damage from y'all) and things start to get silly.

Bold y'all're level xx with +five modifier to Dexterity and carrying a rapier (you'd probably have at least a +1 weapon past this point but we'll get out that out for now), if y'all hit a surprised target that fails their saving throw, yous're going to inflict (1d8 + 20d6) x ii piercing impairment y'all could dish out 128 piercing damage in one hit (the boilerplate is about 74).

Equally a side notation, if you multiclass into Grave Domain Cleric and apply your Path of the Grave ability, y'all can double that damage again for the ability to potentially one-shot an Adult Cerise Dragon. Unlikely, yes, but practise you meet what I mean?

If the idea of being a one-shot killing motorcar with a flawless disguise doesn't appeal to you, there are plenty of other sources of inspiration for an Assassin.

You could draw from the Assassin's Creed franchise for a member of an ancient order who can exercise sweetness flips; or play a Warforged to aqueduct the lethal T-m from Terminator 2: Judgement Solar day; or Jaqen H'ghar, the enigmatic acolyte of the faceless god from Game of Thrones.

However you spin it if you want to play a nimble, deadly killer with a flair for social situations, the Assassin is the way to go.