Dungeons and Dragons 5e Guide to Building a Rogue Assassin

For DnD 5e, assassins are ambush masters with quick, deadly efficiency and masterful infiltration skills.  This subclass is probably the best suited for combat as a rogue, utilizing the rogue’s Sneak Attack against enemies with a slower initiative.  No need to hide if I’m faster than my opponents off the jump.  Plus, the added proficiencies with the disguise kit and poisoner’s kit can offer fun options to the game.

When making an assassin character for Dungeons and Dragons 5e, consider the following:

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Choose a race with high Dexterity modifiers

The assassin thrives on a high Dexterity score—attack and damage rolls, AC, Stealth.  Therefore, I want to pick a race with the highest Dexterity modifiers and perhaps a few bonus abilities.  The best three races that come to mind are tabaxi, high elf and feral tiefling.

Tabaxi are cat-like people—often jaguar or leopard—who get a +2 Dexterity/+1 Charisma bonus combination.  Our assassin could be a jet-black panther bounty-killer who stalks his prey like a ranger.  This feline race also benefits from natural abilities like Feline Agility, Cat’s Claws and Cat’s Talent.  Therefore, I have natural speed, stealth and hand-to-hand combat options that would come in handy as a hired killer.

A high elf assassin would be an interesting—yet effective—choice.  With a +2 Dexterity/+1 Intelligence bonus combination and a free cantrip, I could build this rogue as a wizard hunter.  The cantrip I’ll choose is minor illusion, giving me the ability to distract a target as I sneak in.  Plus, I’ll gain proficiency with a longbow, increasing my damage output on ranged attacks.

On the other hand, feral tieflings could offer a variant on this wizard hunter with a +2 Dexterity/+1 Intelligence bonus combo.  However, I’ll replace the cantrip with inherent tiefling spells from Infernal Legacy.  When I become an assassin at level 3, I’ll also gain the hellish rebuke spell.  Now, if I fail to finish my target with the initial strike, I can engulf my foe in 3d10 fire damage.  I’ll need to rest between uses.

Think about backstory—hitman, agent, sacred priest

Playing an assassin comes with options.  So, figuring out a cool backstory and motivation can bring this dark character into the group.

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A hitman could begin the campaign as a nefarious character, learning how to accept a better way of life with friends.  I could play this character as an anti-hero—it’s built into the story unless I’m playing a campaign to destroy do-gooders.  Remember to ease up on the bad guy throttle and try not to be a stick in the mud.

An agent would be a more restrained version of this deadly class, working in tandem with a kingdom or guild.  This agent could lean on the infiltration aspects of the assassin, using martial prowess only when necessary.

The sacred priest concept is one of the more exotic options for the assassin, acting as lethal agents who vanquish foes of a certain deity.  My previously mentioned wizard killers could fall under this umbrella, eliminating those who dabble in the dark arts.  This priest could bring punishment to those who break some sort of wizard law.

Build rogue for combat—Sneak Attack, Expertise, Cunning Action

My first-level rogue should utilize a rapier or katana for lethal combat damage.  Then, a burglar’s pack and a proficiency in thieves’ tools will offer me basic rogue equipment.  I’ll also choose Stealth as a proficient skill—something I’m bound to use often.

As an early-level rogue, I’ll be able to use an assortment of abilities.  Sneak Attack, Expertise, Thieves’ Cant and Cunning Action are my rogue staples.

Sneak Attack grants me an extra 1d6 damage when I have advantage on the attack.  Of course, this damage grows quickly as I level up and becomes crucial for my assassin role.  By the time I choose this subclass, my Sneak Attack damage will be at 2d6 damage.

Expertise doubles my proficiency bonus for skill checks and thieves’ tools.  This means my ability to disarm traps and pick locks is largely increased.  My Stealth will also be enhanced with this bonus, giving me better opportunities for Sneak Attack damage.

Thieves’ Cant is a secret language between rogues.  As an operator of the underworld, rogues communicate with one another through signs and whispers.  I’ll be able to move through criminal elements in the towns I visit.

Cunning Action offers bonus action options—Dash, Disengage and Hide.  The idea is to increase my maneuverability and give me opportunities to keep using Sneak Attack.  Extra movement and the ability to disengage enemies are crucial for my combat survival.  Honestly, this character is more of a glass cannon.  So, don’t forget to move!

The assassin role—Assassinate, Infiltration Expertise, Imposter, Death Strike

When I reach level 3, I’ll gain my first two crucial Assassin abilities: Assassinate and Bonus Proficiencies (poisoner’s kit, disguise kit).

Assassinate adds to the rogue’s basic Sneak Attack ability, granting a critical hit with bonus damage dice on slower opponents.  Whenever I attack an enemy who has not yet taken a turn, I gain advantage on the attack along with a critical hit.  Now, I’ll be able to add the extra 2d6 (at level 3) damage on top of the critical hit weapon damage.

My Bonus Proficiencies with the poisoner’s kit and disguise kit open gameplay options in interesting ways.  One part of the Assassin’s role is to be an infiltrator—and, frankly, we can get Scooby-Doo-level silly with these disguises.  Poison offers a unique damage option after the initial blows are exchanged, often adding extra 1d6 damage on failed Constitution saves.

Infiltration Expertise (level 9) and Imposter (level 13) are the next two abilities I learn, leaning into my disguise kit.  Infiltration Expertise allows me to create a fake identity for myself, established over several days.  Then, Imposter allows me to recreate another person’s voice, handwriting and behavior.  Though the idea here is to get to a target and eliminate that person, I could repurpose these abilities for all kinds of creative uses.

Death Strike is my ultimate move, forcing opponents to make a Constitution saving throw or take DOUBLE my already critical attack damage.  At level 17, this includes 9d6 Sneak Attack damage.

Utilize higher-level rogue abilities

At higher levels, my assassin will learn a list of cool rogue abilities that will enhance my combat and role in the group.

  • Uncanny Dodge allows me to use my reaction to half melee attack damage against me.—Level 5.
  • Evasion grants me the ability to take 0 damage on successful Dexterity saving throws for magical area effects. Normally, this would be half damage—Level 7.
  • Reliable Talent allows me to treat a d20 skill check of 9 or lower as a 10. Therefore, I can’t roll anything less than a 10 before adding my modifiers. This only works for proficient skills—Level 11.
  • Blindsense gives me the ability to sense creatures within 10 feet of me when in total darkness. This will come in handy if I need to do any real assassination missions. Level 14
  • Slippery Mind gives me proficiency with Wisdom saving throws. This defensive bonus will keep me from falling into charm or fear—Level 15.
  • Elusive negates advantage on enemy attack rolls. Therefore, I’ll keep my edge in quick maneuverability.  Level 17
  • Stroke of Luck grants me an automatic hit when I miss.  This goes for combat or saving throws, needing a rest between uses.  Level 20.

To Sum it Up

The Assassin has a mixture of roles within a party: lethal damage dealer, trap finder and infiltrator.  Therefore, this character is the party’s ninja, skulking in the darkness to cover our flank and root out ambushers.  Utilizing a finesse sword (shortsword, rapier, katana), I can increase the effectiveness of my Assassinate ability.  Plus, the poisoner’s kit can add a unique effect to my ranged attacks.

My roleplaying options are varied, but definitely on the darker side of character development.  One of my favorite hooks is the wizard hunter.  I could tie this into the story in interesting ways and play a half elf or feral tiefling.  Plus, my poison is more likely to work on these enemies—as opposed to undead or supernatural beings.

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