Learning to play a Mastermind Rogue

Last weekend, getting ready to move a few hours away, I had to say goodbye to my usual D&D group, and— by extension— my rogue.

Admittedly, I’d spent months regretting the build, a Mastermind-archetype Rogue in a room full of fighters, paladins, and rangers, but something about him had grown on me in the last few sessions. After it ended, I realised what it was: I finally learned how to play that class.

For a bit of background on it, the Mastermind is a new-ish archetype for the D&D 5th edition Rogue class, introduced in the “Xanathar’s Guide to Everything” addendum. Unlike the Assassin or Arcane Trickster archetypes, the Mastermind firmly places it’s flag in the “Cloak” part of “Cloak and Dagger”. At the start, they come with two abilities: use the “Help” action as a bonus action from up to 30 feet away, and accurately mimic the accents of anyone they’ve listened to for more than a minute.

For a lot of you reading this, you’ll think (as I did), “Wow! What an interesting and useful set of skills for a person in the world!” And in most cases you’d be right, except, I was playing with a table of combat-focused number crunchers. The rogue is not a particular combat-ready class in even the best circumstances (though if you can play a lawful evil assassin at any point in your life, I highly recommend it), and playing the Mastermind skewed my stats away from Strength and Dexterity enough that my usual effectiveness was, at its peak, nil. I was knocked out my very first session with this group, and only barely avoided death itself.

Despite my better judgment, though, I opted to stick with the character, and learned a thing that I hope will help you in your roguish endeavours:

Stop rolling the dice.

There, I said it. That’s the whole of my advice. Just, stop rolling. You can do it!

A thing I noticed after playing the Mastermind for a few sessions is that, unless you really want to lean towards combat or role-playing, you’re kind of just bad at both, numerically-speaking. Especially until you reach 6th level and start getting actually helpful rogue things, like Uncanny Dodge, or your second round of Expertise. If you’re rolling a new character and the table is already starting at level 3 or 4, you’re really buckling in for a few levels of bad rolls, especially if your party is just going around looking for a fight.

My particular rogue tried splitting the uprights between Dexterity and Charisma, and at level 6 had a +3 in each. Not horrible, but compared to the Dwarf fighter’s +5 Strength, my combat skills were lacking considerably. Rogues also get multiple attacks later than other classes, and typically have lower armour values, so if you miss that sneak attack, you’re pretty much always hosed the next round.

As a result of this, I decided to begin playing my own game within D&D, which was to see how long I could go before my character absolutely had to take a risk. I figured if I didn’t roll the dice, I wouldn’t have the chance to fail.

Weirdly, it kind of worked.

Rather than engaging in combat directly, I used the Mastermind’s help ability to grant my party advantage from a distance, while the rogue’s Cunning Action let me move and hide that same turn. From a safe distance I could “help” the combat along by firing a hand crossbow, but that only ever did minimal damage. The real damage would come from the paladin that I’d just given advantage to, and who consequently drew attention away from the hiding rogue (no matter how bad my stealth roll was).

Similarly, rather than engage directly in role-playing situations that might require single deception/persuasion rolls (for example, lying to the cult leaders about who we were and why we were there), I purposefully spent time performing smaller actions that could lead up to that interaction. Part of this, I learned, involved being the opposite of the typical rogue, and spending lots of money. “You have to spend money to earn money”, as they say. In my case, that money went towards forged identifications, hiring thieves to go do my work for me, purchasing a variety of nice clothing, joining a temple, and slowly falsifying documents for no less than three distinct personas whose reputation would precede them. It’s amazing how much a few gold can do for one’s reputation when placed in the right hands.

I’ve written previously about how spending money in D&D is sort of a non-issue past a certain point, so if nothing else I encourage you to spend it any way you can. Hirelings are a perfect straight-from-the-book example that I haven’t seen enough players take advantage of. Not to carry your things, but may to head to the next town over, and talk loudly about how someone matching your description has just slain a mighty beast.

The end result of all of this is that when it did come time for me to roll the dice, it was largely on my own terms. The prep work combined with a few rolls for insight or investigation would often grant advantage, and even when it didn’t (or I failed anyway), the information received would be enough to weigh my choices without crossing the line into meta-gaming.

I’ve read a lot of places now that the Mastermind rogue is basically the support class of rogues, and I feel like that’s largely true. But, in true rogue fashion, I encourage you to not thing about it in terms of supporting your party, but supporting yourself. Rather than leaping to action with the fighters and the sorcerers and those other impulsive classes, ask yourself:

What are the things that your character can do in the moment that A) Don’t involve rolling the dice, and B) when it comes time to roll the dice eventually, will give them the best shot at success?