Find out what occupation the mastermind in your story has– such as prince, queen, or king.
Then it may be best to build a rogue that fits that character type so you can keep the character in line with its society’s expectations and not detract from the restrictions of being a member of high society. A rogue might make a more appropriate martial artist than an assassin for example.
The best build for a mastermind rogue in D&D 5e is an Expert, with the Assassin subclass.
A mastermind rogue in D&D 5e is someone who likes to measure her targets weaknesses, and then sneakily exploit them. An Expert with the Assassin subclass fits this idea well because they are great at finding out their enemies’ weakness, and once they find it, know exactly how to use it against them. Plus being a finesse weapon user means you can attack your enemy’s armor easier than bashing through their defenses head on. Your encumbrance won’t be as much of an issue either, since you’ll mostly be using daggers as your weapons.
The best build for a rogue in D&D 5E if they are playing a mastermind build is the skillful dodger.
The best way to play a mastermind character is to be sneaky. That means that it’s usually better not to fight, and instead escape or outwit your opponents. If you can’t do that, then try hitting the enemy with knockout poisons and knock them out before they ever hit back. Being able to dodge is among the most important things since you will need it all the time at low levels when enemies take attacks of opportunity against you while you sneak around, but also as an escape mechanism after thieves’ tools breaks and somebody starts chasing after you. Finally, being able to use disguise magic allows you to disguise yourself as someone else, which can be quite helpful if you’re trying to frame somebody else for your crimes.
The rogue has the best skill list in D&D 5E, but it also has the worst ability scores and only 1d8 hit points. This means that there are many different builds that can achieve similar things. For a mastermind, it’s probably best to consider the skillful dodger build, but other rogue builds such as the thief and burglar (which use Dexterity for their skills) could be pretty effective too.
Creativity is key in a mastermind build, so test out different builds and think on what your Intuitive talented rogue can do best. Subterfuge Rogue as well if you’re feeling up for it.
If you want to create a mastermind build, consider multiclassing so that your main character has both Rogue and Monk levels for abilities like Ki-Empowered Strikes.
Dungeon masters don’t usually design mastermind builds because they’re complicated to make, but there’s nothing stopping them from playing masterminds in their games. Multi-classing is key as this will give the player access to the rogue’s sneak attack damage ability, and monk levels give great mobility with plenty of manoeuvrability options making it easier to get sneak attacks on opponents. This also means that the player doesn’t have many dependency on weapons when using unarmed strikes–which may come in handy if access to weapons is limited or they burn up all their resources before facing the final battle.
A rogue monk build can also be played as a ranged attacker with darts, throwing daggers and shuriken, or simply using their bare hands if unarmed strikes are available. The goal of this article is to present several different mastermind builds for rogues for D&D 5E that you can try out during your next play session.
Note: These mastermind builds are not as complex as those you would find in Pathfinder, but it’s more than enough to make a character that thinks and acts like a mastermind should.
The best build for a rogue mastermind, in D&D 5e, is Halfling Rogue (Thief).
The Halfling’s small size allows it to sneak up on larger foes and steal their loot.
Their natural stealth coupled with the Thieves’ Cant come in handy for any curious character looking for a challenge! Their innately higher dexterity and speed provide additional benefits. Whichever you choose, the smallest race always has its advantages.
In addition to your skill sets that first-timers will find useful like Acrobatics or Athlete, an elusive Stealth or even Inquisitive type of background can help shape your uncanny ability to stay up only three feet from the enemies while they remain unaware of your escape paths.
Other sources for rogue builds include:
* Dungeon Master’s Guide
* Player’s Handbook
* Xanathar’s Guide to Everything
Thief (Roguish Archetype)
Rogue (Mastermind Archetype)
Any ingame race not from the Forgotten Realms. Rogues should use racial traits that are most likely to antagonize DCs and NPC reactions on the first try. If you are BG or LG, stay away from anything erfaring. If you’re CN, it’s about 50/50 from my experience. For example, I’m a Noldorian Elf rogue with a few bard-like abilities under my belt simply because rogues can’t get disadvantage on Deception checks in game rules like bards do in reality but I have to be stealthy when I cast them so as to not break stealth mode.
The Rogue’s Expertise in stealth lends itself well to this role. Choose backgrounds that reflect your desired intelligence and personality, such as academic background or noble/king’s general servant. Take skills like Deception and Insight.
One of the major schools of crime developed by William Kennerth Thompson- is one which has been expressly designed for the mastermind assassin. Here, Thompson lays out a detailed roadmap on how he planned for his assassins to infilitrate high society, identifying the target’s daily habits with utmost scrutiny before stabbing them in their own home or other “safe zone” while they were unsuspecting- taking care to do so when guards were absent! In fairness, most of this type of assassination also involves murdering the target’s entire family as well- often including their servants- so they have no one to turn to after they’ve been killed.
Anyways, most of this roadmap is what we’ll refer to as “social engineering”- with a specific focus on interpersonal relations: knowing who someone is and how best to use that information against them. However, don’t ignore the “physical engineering”- as a mastermind, you should also know how to utilize a weapon and equipment that is not only easy to conceal- but can be used against your enemies with maximum efficiency.
To this end, I think the Rogue’s Expertise in stealth fits Thompson’s vision for his assassins well: going back to our example of a “noble’s servant”, perhaps your character’s family is known as the most loyal and trusted servants for several generations- so it makes sense to have them trained in weapon skills from a young age.
Would a mastermind rogue need to be concerned with stealth? No. A mastermind’s primary focus is subterfuge and negotiation, not stealth. Stealth might be an aspect of the game you’re playing with your GM, but it doesn’t really fit this kind of question about builds for a mastermind build.
Is there any good background to choose as the wealthy noble? Yes. Your background should match your proficiency bonus, so wizardry or magic backgrounds are good choices if you have proficiency in Arcana or Occultism respectively.
I’m a spellcaster that knows some spells of another type what would be effective? Yes! Some good options are transmutation spells that change terrain features such as mountains into hills (casting Mold Earth) or changing the area into difficult terrain (casting Grasping Vines) to hinder pursuers. These are both druid spells that can also be cast by the spellcasting feature of certain monsters.
Rogues have the widest array of class skills and subsequently, they can excel in a wider variety of builds. That being said, there are many different types of mastermind rogues out there and there’s no “best” answer as each build has its own set of pros and cons.
There are some very strong arguments to be made for Nightstalker for stealthy infiltration into unsuspecting communities that only find out too late who they’ve welcomed into their home or dungeon (detecting these rogues is not easy), Mastermind for switching stances between flanking opponents while keeping the rest at bay with metered bursts from sneak attack damage (masterminds get the most versatility with ability to grapple foes in fear-inducing manner), any number of hybrid builds that combine one or two of the above, and so on.
From a flavor perspective there’s also no “best” build. While many rogue players would prefer their character to be sharp-witted, charming, dexterous in combat while possessing superior knowledge in various fields to help further whatever agenda they choose to pursue (unlike wizards and clerics), there’s no explanation on why they can’t be all of these things while also being a supernaturally good fighter with an emphasis on speed (à la monks).
My personal recommendation is that you pick your favorite rogue archetype and focus on that. You can use one of the many tools available to optimize your character, such as this one which will tell you just how much damage you’ll be dealing on average with sneak attack.
In the end, all players have their own preferences and it’s up to them to decide what they want from a build. In fact, many of the most-used builds in D&D 5E were not even designed to be used by rogues in the first place (e.g., scout, eldritch knight).