Mastermind Rogue Guide

Introduction

The Mastermind Rogue works best in a game with a lot of intrigue and social interactions. The only feature which applies in combat situations or in a dungeon crawl or something is Master of Tactics; everything else is for social situations. You can scrape by on core Rogue class features, but outside of a highly social campaign, the Mastermind is going to struggle compared to other Rogues. Even in campaigns where the Mastermind is well suited, you will need to work to make your features meaningful and your DM will need to tailor the game to your capabilities.

Master of Tactics adds a tiny taste of Support to the Rogue’s capabilities, but using it comes at the cost of things that the Rogue already does well. The Mastermind’s other tactics support your ability to play a Face, but in the vast majority of campaigns, they my see exceptionally rare use.

Table of Contents

Disclaimer

RPGBOT uses the color coding scheme which has become common among Pathfinder build handbooks, which is simple to understand and easy to read at a glance.

  • Red: Bad, useless options, or options which are extremely situational. Nearly never useful.
  • Orange: OK options, or useful options that only apply in rare circumstances. Useful sometimes.
  • Green: Good options. Useful often.
  • Blue: Fantastic options, often essential to the function of your character. Useful very frequently.

We will not include 3rd-party content, including content from DMs Guild, in handbooks for official content because we can’t assume that your game will allow 3rd-party content or homebrew. We also won’t cover Unearthed Arcana content because it’s not finalized, and we can’t guarantee that it will be available to you in your games.

The advice offered below is based on the current State of the 2014 DnD 5e Character Optimization Meta as of when the article was last updated. Keep in mind that the state of the meta periodically changes as new source materials are released, and the article will be updated accordingly as time allows.

Mastermind Rogue Features

  1. Master of Intrigue: A pile of proficiencies which you might never use, but in an intrigue game this offers some very exciting tools.
  2. Master of Tactics: Help gives the target Advantage on an attack or check, which is pretty great for a lot of characters. Of course, as a Rogue, no one needs Advantage as much as you. Using this as a Bonus Action prevents you from using Cunning Action, Steady Aim, or two-weapon fighting, so your Bonus Actions will always be a very difficult trade-off.

    A good use case would be to use Master of Tactics to give your party’s Fighter-equivalent Advantage on a check to Shove your enemy prone, then wait for Advantage on subsequent turns. If the initiative order supports it, you could Ready an attack and wait until your target is prone before attacking them.

    If you’re using this with more of a focus on helping your allies, martial allies will get diminishing returns once they pick up Extra Attack at level 5. Allied spellcasters may get more value for high-damage spell attacks, but spell attacks disappear after Vampiric Touch at 3rd level. Unless you have someone leaning heavily on Inflict Wounds or Vampiric Touch like a Death Cleric, you may not find a spellcaster who actually cares.

  3. Insightful Manipulator: A fun way to metagame, but not always useful since in most games you typically won’t get to spend a minute chatting up enemies before weapons come out. If you’re able to observe your target while hiding, you can trigger this against creatures will be immediately hostile when they see you.

    In intrigue games this could be a neat way to learn about a creature, but you don’t get a novel way to make this information mechanically useful, so it’s often little more than trivia and a hint at how the creature is built. In combat, knowing the target’s lowest mental stat can be helpful information for your party’s spellcasters so that they can target your enemies with save-or-suck spells.

  4. Misdirection: I think the intent is to use enemy creatures as cover while you’re being attacked at range, but that simply doesn’t happen. Few enemies rely on ranged attacks, and most which do so can also produce area effects, or they could target one of your allies, such as that soft, squishy Wizard over there.

    In the rare situation where you are targeted by a ranged attack, your best bet is to hide behind an ally. It can be a bit rude to shuffle attacks onto an ally, but if you’re using a well-armored ally as cover, sometimes your ally may be better suited to absorb the attack, and your party’s Defender generally goes into combat explicitly hoping that they’ll draw attacks away from you and your other squishy allies.

    Lightfoot Halflings have the ability to hide behind creatures one size larger than they are, which will often also give you cover. Of course, if you’re hidden, you’re also untargetable, which entirely negates the need for this feature.

  5. Soul of Deceit: Very situational. Characters in a typical campaign might be subject to such effects once or twice if they run a full campaign from levels 1 to 20, and, even in a intrigue campaign where you might face other sneaky people with options like telepathy or spells like Zone of Truth, those options are typically limited to powerful characters and won’t be applied to you so frequently that this is justifiably as a level 17 feature.

Mastermind Rogue Ability Scores

No different from a typical Rogue.

Mastermind Rogue Races

Little different from a typical Rogue. The lightfoot halfling will get less value out of Misdirection, and the Monsters of the Multiverse Hobgoblin will get much less value out of Master of Tactics, so I recommend avoiding them.

Mastermind Rogue Feats

No different from a typical Rogue.

Mastermind Rogue Weapons

Little different from a typical Rogue. Two-weapon fighting is less appealing, but your other options are still good.

Mastermind Rogue Armor

No different from a typical Rogue.

Mastermind Rogue Multiclassing

No different from a typical Rogue.

Example Mastermind Rogue Build – Criminal Mastermind

We’re going to build a criminal mastermind; a master of deception, trickery, mischief, and helping their allies be their best selves (at least tactically). This build will work great in an intrigue game, but your effectiveness in combat may depend heavily on your allies’ builds since the Mastermind Rogue’s biggest combat options are support features.

We’ll include the Steady Aim Optional Class Feature.

Ability Scores

Fairly standard for the Rogue, but we’ll put more into Charisma than most Rogues would.

BaseIncreased
Str88
Dex1517
Con1414
Int88
Wis1212
Cha1415

Race

Custom Origin Hobgoblin (using the Volo’s Guide to Monsters stats). We’ll get the standard +2/+1, Darkvision, two martial weapon proficiencies (heavy crossbow, whip), and Saving Face. Hobgoblins frequently lead groups of goblinoids, so it feels like a good option for a Mastermind.

Background

Criminal. Because it’s the whole theme of the build, and it’s also a pretty good choice for the Rogue. Proficiency in Thieves’ Tools is redundant, so trade it for a different tool kit or another language. We’ll get proficiency in Deception, Stealth, and a gaming set.

Skills and Tools

We’ll use our four class skills to take Insight, Intimidation, Perception, and Sleight of Hand. We’ll get Deception and Stealth from our background. Criminal also gives us proficiency in one gaming set. Choose playing cards as your gaming set because somehow that feels like the most nefarious of the gaming set options.

At level 3 we get proficiency in Disguise Kit, Forgery Kit, and another gaming set. This time we’ll pick Dragon Chess.

Feats

At level 4 we’ll take skill expert and increase Dexterity to 18.

At level 8 we’ll take Piercer and increase Dexterity to 19. Yes, yet another Rogue with Piercer.

At level 10 we’ll split an ASI to increase Dexterity to 20 and Charisma to 16.

At level 12 we’ll take Inspiring Leader.

At level 16 and 19 we have open feats. Mobile and Skilled could both be good choices. Magic Initiate to get Booming Blade would also work.

Levels

LevelFeat(s) and FeaturesNotes and Tactics
1Expertise
– Deception
– Intimidation
Sneak Attack +1d6
Thieves’ Cant
We’ll use Expertise to improve our social skills and lean into being our party’s Face. We don’t take Persuasion because we’re a criminal mastermind and we don’t like to say “please.”

For now we’re a typical Rogue. Grab a heavy crossbow as soon as you can afford one for the slightly larger damage die. If you miss with attacks, don’t forget to use Saving Face. Up to a +5 bonus is massive in 5e.

If you want to be in melee, typical Rogue weapons (rapier, etc.) will work, but consider using a whip. It’s the only Finesse weapon with Reach, so you can deliver Sneak Attack without getting into melee with most enemies. This will become important when we get Master of Tactics at level 3 and can’t rely on Cunning Action (Disengage) to get us out of melee for free.
2Cunning ActionNormal Rogue stuff.
3Subclass: Mastermind
Master of Intrigue
Master of Tactics
Steady Aim
Sneak Attack +2d6
Master of Intrigue gives us some additional tool proficiencies, plus two languages.

Master of Tactics and Steady Aim give us two more uses for our Bonus Action. Someone in the party is getting Advantage every round. Maybe us, maybe our allies.

If you’re in melee, look for an ally to Shove enemies prone for you. Use Master of Tactics to give them Advantage on the check to do so. If you’re fighting at range, giving an ally Advantage on an attack roll may be the best you can do. Try to time this to help allies with big attacks like leveled spells. Death clerics hitting enemies with Inflict Wounds or Vampiric Touch are good options.
4Feat: Skill Expert
– Dex 17 -> 18
– Proficiency: Persuasion
– Expertise: Stealth
We’ll continue to emphasize our skills.
5Uncanny Dodge
Sneak Attack +3d6
6Expertise
– Insight
– Perception
By this level we’ve been betrayed, hoodwinked, bamboozled, and otherwise fooled enough to know better, so we’re taking Expertise in skills to make sure it stops.
7Evasion
Sneak Attack +4d6
8ASI: Piercer (Dex 18 -> 9)Yes, Piercer on yet another Rogue. Look, it works really well when all of your good weapon options deal Piercing damage. If you’re using a whip, consider Slasher instead.
9Insightful Manipulator
Sneak Attack +5d6
Insightful Manipulator encourages us to have extended conversation with potentially hostile creatures (or to hide and observe them) so that we can metagame a bit. Remember that this only tells you if the creature’s stats are better, worse, or equal to yours. Fortunately, most creatures have proficiency in saves which match their high ability scores. If you get into a fight, be sure to share this information with your party’s spellcasters.
10ASI: Dex 19 -> 20, Cha 15 ->16Split an ASI to improve both of our ability modifiers.
11Reliable Talent
Sneak Attack +6d6
Our floor on our favorite skills is now good enough that most creatures will struggle to oppose us when we lie, cheat, and steal.
12Feat: Inspiring LeaderWe have all of this Charisma, and we’re trying to establish ourselves as the Face and the leader of our party. There’s a feat for that, and it’s pretty fantastic.
13Misdirection
Sneak Attack +7d6
Hide behind your allies. If they have a summoned creature or some other combat pet, that’s ideal because you’re not using another player as a potentially unwilling shield.
14Blindsense
15Slippery Mind
Sneak Attack +8d6
16Feat: AnySee above.
17Soul of Deceit
Sneak Attack +9d6
We’re so good at lying that even magic and telepathy can’t stop us.
18Elusive
19Feat: Any
Sneak Attack +10d6
See above.
20Stroke of LuckA pretty good capstone, and it will save you use of Saving Face.