The Ultimate 5e DnD Mastermind Guide

Years of screening, training and careful testing can be undone with a simple trick. When the Reverend Mother comes to read your mind and test your suitability to serve the Emperor, she will see only what you choose to show her. And her mistake will take you one step closer to your mark…

Table of Contents

There’s no subclass better equipped for impersonation, disguise, and intrigue than the Mastermind. Their capacity for linguistics, tactics, and manipulation is perfect for campaigns with nuanced NPCs and competing factions. At higher levels, they can’t be lied to and can even project false thoughts to anyone attempting telepathy.

But these exceptional social abilities come with a tradeoff. In terms of combat, this Rogue subclass can feel underpowered for some. The Master of Tactics ability allows Masterminds to alert their allies to key openings in battle, granting advantage. This is great for roleplay and creates a sense of camaraderie at the table, but (for some players) doesn’t make up for a lack of offensive ability.

Mastermind is a great choice for a dedicated roleplayer with a DM who also loves this style of play. But it’s (arguably) the least suitable for a combat-heavy dungeon crawl. This archetype is awesome in the right situation but worth approaching with caution.

How to Use This Guide

Everything in this guide has an emoji, ranking how useful a given ability or feature is to playing this class effectively.

✅ — An absolutely crucial feature. Often forms the backbone of a class’ look and feel. Will provide some bonus that can’t be found through other means.

🆗 — A solid feature that does its job well. Not game-breaking, and certainly replaceable, but a strong choice that shores up some weakness.

⚠️ — A debatable choice. Could work for a specific build, but otherwise is either a wasted opportunity or is just weaker than other alternatives.

⛔ — Outright bad and detrimental. This weighs down the class and just takes up space on the character sheet. A weakness you will have to accommodate for.

These rankings are meant to help you create an optimized class build, but remember DnD isn’t a game where you need to win to have fun. Weaker but flavorful builds also have their place and can make for fulfilling characters.

How To Play A Mastermind

A Machiavellian Schemer with a dash of street-savvy rogue, the Mastermind uses words as often as weapons. Professor Moriarty might be fiction’s best-known mastermind archetype. Using intellect, education, and an underground network, he influences the world around him while evading capture—classic Mastermind stuff. Tyrion Lannister is a great example of this archetype in fantasy. He also uses his mind to achieve his ends—but without such diabolical intent. There’s no requirement for a Mastermind to be aligned towards evil, after all.

Infiltration, Influence, and Manipulation

The base rogue has some capacity for infiltration via stealth and deception. The Mastermind subclass increases these capabilities significantly. Through proficiency with the disguise kit, forgery kit, and exceptional language skills, the Mastermind can maintain cover and gather intelligence once behind enemy lines.

The Mastermind can impersonate any creature they’ve listened to for more than 1 minute so perfectly as to pass a native speaker of that land. Language proficiencies and a gaming kit the Mastermind carries around make this a great way to gather information, gain trust, and find informants.

At mid-level play, the Mastermind can assess an NPC/creature’s strengths and weaknesses by observation alone. This plays into their role as the party’s information-gatherer. The Mastermind’s thoughts can’t be read by magical or telepathic means at higher levels. They can even present false thoughts to any creature trying to read their mind. This creates lots of options for intrigue and manipulation at these higher levels of play. 

Supporting Allies and Misdirecting Attacks

The Mastermind is primarily a support class, depending entirely on base rogue abilities for offense. Their utility in combat comes from giving advantage to their allies using Master of Tactics and an ability to cause attacks intended for them to target other creatures nearby. 

Supporting your party by calling out the enemy’s weak spots in the heat of battle works for a lot of roleplayers. “Go for the eyes!” gets a lot of mileage at our table but feel free to get as creative as you want with your tactical advice —your Mastermind has read the codex/bestiary! 

You’ll often have to choose between Cunning Action or Master of Tactics as your bonus action. There are times when you want to assist one of the heavy-hitters in your party line up that perfect shot, but an enemy is also threatening your position. Many players choose to build a ranged Mastermind to facilitate this kind of play. Fighting from distance requires fewer uses of cunning action than fighting in melee range, something the Mastermind can capitalize on, granting advantage to an ally most rounds.

Mastermind Subclass Features

The Mastermind is a master of languages, disguise, and intrigue. But underpinning that, the core rogue features mean this archetype is still dangerous – just perhaps not as directly dangerous as other roguish subclasses. Aiding the party with sound tactical advice, slipping attacks directed at you, and bamboozling others with your mental prowess are at the heart of the Mastermind subclass features. 

Level 1 (Rogue)

✅ Sleight of Hand

This is your ability to make quick movements with your hands, unnoticed. The DM can ask you to roll Sleight of Hand when you want to pickpocket something, stash an object on a creature, or drop poison in a goblet.

✅ Expertise

This allows you to double your bonus in two skills you are proficient in or do the same for one skill and your thieves’ tools proficiency. 

✅ Sneak Attack

Once per turn, you can deal an extra d6 damage to a creature you’ve already hit so long as you have advantage on the roll. If the creature you’re targeting is within 5 feet of a creature hostile to it (often a member of your party), you don’t need advantage to deal Sneak Attack.   

🆗 Thieves’ Cant 

This secret language has a spoken component understood by fellow rogues and scoundrels and a set of rudimentary markings that can help identify safe houses, supply caches, and areas of interest to other rogues.

Level 2 (Rogue)

✅ Cunning Action 

Cunning action is a representation of your heightened reflexes and uncanny speed. As a bonus action, you can do one of the following three things:

  • Dash allows you to cover twice as much ground as usual. 
  • Disengage means you can retreat from melee range without provoking an Opportunity Attack.
  • Hide lets you attempt to disappear from view, potentially gaining another Sneak Attack (you must disengage before you can hide).

Level 3 (Mastermind)

✅ Master of Intrigue

This gives you proficiency with the disguise kit, forgery kit, a gaming set of choice and allows your Mastermind to learn two additional languages. This linguistic ability extends to mimicry. With 1 minute of observation or interactions, the Mastermind can copy the accent of any creature well enough to pass as a native speaker (provided they know the language). 

✅ Master of Tactics

This allows the Mastermind to use Help as a bonus action, granting advantage to their target. In addition, the creature targeted by your ally can be up to 30 feet away from you, instead of the standard 5 feet.

Level 5 (Rogue)

✅ Uncanny Dodge

Uncanny Dodge means the rogue can react to an incoming attack from a visible enemy, halving the damage.

Level 7 (Rogue)

🆗 Evasion

When targeted by an area of effect attack, you can react and make a saving throw. If you pass the saving throw for this type of attack, you take no damage. If you fail, you take half damage.  

Level 9 (Mastermind)

🆗 Insightful Manipulator

After 1 minute of observing or interacting with a creature outside combat, you can assess whether the creature is equal, superior, or inferior to you in two of the following characteristics of your choice: 

  • Intelligence score
  • Wisdom score
  • Charisma score
  • Class levels (if applicable)

The DM can also give some information about the creature’s history or personality traits, depending on the situation.

Level 11 (Rogue)

✅ Reliable Talent

You’ve practiced your skills until even on your worst day, you can still expect a certain standard. When you make a roll with a skill you are proficient in, anything rolled 9 or less on a d20 is automatically converted to a 10.

Level 13 (Mastermind)

🆗 Misdirection

This represents how hard it is to pin down the Mastermind in combat. When you have partial cover from a hostile creature within 5 feet, you can cause attacks directed at you to target that creature instead.

Level 14 (Rogue)

🆗 Blindsense

As long as you can hear, you can sense the presence of illusions and invisible creatures within 10 feet.

Level 15 (Rogue)

🆗 Slippery Mind 

This represents your rogue’s experience gained from years of adventuring. You gain proficiency in Wisdom saving throws.

Level 17 (Mastermind)

⚠️ Soul of Deceit 

Your mind has developed natural resistances and counters to telepathy, making it impossible to read your mind unless you allow it. You can also make a Charisma (Deception) check contested by a creature’s Wisdom (Insight). If the creature fails, you can present false thoughts that seem convincing. 

  • No matter what magic is used to determine if you are telling the truth, it always appears as though you’re being truthful if you so choose. 
  • As much as this can be a powerful tool in a heavily social, courtly intrigue-type campaign, it feels like a let-down compared to many other 17th level abilities in the game. Has potential in a very specific kind of game only. 

Level 18 (Rogue)

✅ Elusive

So long as you are conscious and capable of movement, you no longer suffer disadvantage on attack rolls against you.  

Level 20 (Rogue)

✅ Stroke of Luck

You can turn a failed ability check into a 20 or a miss into a hit in combat once per long rest using this ability. 

The Classic Mastermind Build

Like all rogues, the Mastermind needs a high Dexterity score to function best. Even once you specialize as a Mastermind at 3rd level, sneaking, hiding, and maximizing the element of surprise are still an important part of this subclass’s gameplay loop. Abilities like Deception, mimicry, and Soul of Deceit are governed by your Charisma score, which should be your next priority for ability score increase as a Mastermind. Don’t sleep on Constitution either. Once the bad guys figure out you’re the brains behind the operation they’ll try to take you out. 

This feels like a subclass built for roleplay. Giving advantage to your allies and causing shots intended for you to strike your enemies makes for epic moments in the hands of an enthusiastic roleplayer. But the real appeal of playing this subclass is its capacity for intrigue and manipulation outside of combat. 

A Mastermind build (that wants to optimize their high-level subclass abilities) is one focused on Charisma, with skills, feats, and proficiencies that support subtle manipulation, clandestine deals, daring impersonations, and brilliant plans. Like we mentioned—not for everyone but a roleplayer’s delight. 

Ability Scores

⛔ Strength

Typically a dump stat for Masterminds. Other members of the party have this covered.

✅ Dexterity

This is your key ability score as a rogue and remains vital in combat and stealth as a Mastermind.

🆗 Constitution

Important for every class and The Mastermind is a fairly squishy subclass. At the same time, you can’t afford to drop a lot of points in here.

⚠️ Intelligence

Despite what we might naturally assume, this is not especially relevant to the Mastermind.

🆗 Wisdom

As a roguish character, Wisdom (Perception) can be important during exploration. Wisdom saving throws are also useful.

✅ Charisma

Apart from Dexterity, this is your key ability score as a Mastermind. Your capacity for deception, manipulation, lies, coercion, and influence all stems from this score. 

Racial Considerations

Like we said, bonuses to Dexterity and Charisma are the most important concerns when choosing a race for your Mastermind Rogue. While traits like darkvision, decent constitution, or access to feats can be important to a specific build, the Mastermind is very much a rogue in combat. Dexterity represents your Attack and Damage modifier and you’ll need it as high as possible to feel effective in battle as this subclass. 

✅ Lightfoot Halfling

With +2 to Dexterity, +1 to Charisma, +1 to Constitution, and the Naturally Stealthy ability, the Lightfoot Halfling makes a great Mastermind Rogue. Hiding behind your party members or hostile creatures is a useful feature for any rogue, making more Sneak Attacks possible. And the Lucky ability (any 1 rolled on a d20 must be rerolled) seems to fit the archetype, who don’t seem prone to making critical failures. The mechanics support it and as a character concept, a clued-in halfling Mastermind sounds like a lot of fun. 

 🆗 Half-Elf

The +2 to Charisma that comes with choosing half-elf helps with the Mastermind’s social abilities like manipulation, deception, and influence. The bonus languages synergize with Master of Intrigue, making you a first-rate impressionist. +1 to Dexterity and +1 to Constitution give you some combat-readiness, darkvision is a useful trait for a rogue, and Fey Ancestry helps you resist sleep and charm spells—all useful features. To round it out, Skill Versatility at level 3 gives you access to a bunch of extra proficiencies, extending the feeling that your character is truly a Mastermind. 

🆗 Variant Human

Variant human gives you +1 to two of your ability scores, probably best spent on Dexterity and Charisma. The feat available at level one can be used to further specialize your character in several ways. Choosing Magic Initiate as your feat, for example, could give you access to Illusion cantrips early on, augmenting your roguish skills. Comprehend Languages could also mesh well with your social abilities, Dungeon Delver might work if your Mastermind is the party’s chief explorer, etc. But our top pick is Magic Initiate, taking Bard. There are several useful options and they depend on our already decent Charisma score. 

✅ Tiefling

  • Bloodline of Dispater: Tiefling are a good candidate for a Mastermind already with their +2 to Charisma and darkvision. But the Dispater variety throws in +1 to Dexterity then at later levels, Disguise Self and Detect Thoughts – both very useful spells and based off your Charisma score.
  • Bloodline of Glasya: Named for the criminal mastermind of Hell, the Glaysa bloodline are born with innate abilities that help them in this role. The +2 Charisma from Tiefling is complemented here with a +1 to Dexterity and several heist-friendly spells. The Glasya Tiefling can cast Disguise Self, Minor Illusion, and Invisibility once per long rest, using Charisma as their modifier. 

The 5e Mastermind — A Cautious Recommendation

The Mastermind isn’t going to be for everyone. It’s only suitable for roleplay-centered, plot-heavy campaigns. And even then, while the Mastermind is out carousing and whispering secrets, the DM risks losing the interest of the other players at the table who can’t contribute much to this kind of gameplay. There is some cool stuff here, no doubt. But approach with caution and be sure to bring it up with your DM before rolling up your Mastermind. 

Let us know if you got anything from our breakdown or if we missed anything cool about this subclass. 5e makes so many unique builds possible that we’re sure someone has got something cool we haven’t even thought of. Please share this with your gaming group and hit us up in the comments if we’ve missed anything or if you’ve got a Mastermind-related story for us…

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