I need help.  I’m not new to D&D (four years under my belt), but I have never seen anyone play a Mastermind rogue.  Now, as a new DM, one of my players has selected Mastermind for her future subclass.  I’ve read the description in Xanathar’s several times, and it just doesn’t look that great— but of course, having no practical experience or observations, it’s not unlikely that my impression is wrong. 

Can anyone help me understand how the Mastermind subclass works?  In what kind of situations would it work well?  What are the pros and cons?   Her alignment is True Neutral, if that makes a difference.

Mastermind is an odd one, instead of getting a way to more easily trigger sneak attack, they get a way to give advantage to others.   It particularly shines within 30ft with an ally that does strong single hits such as a paladin, someone with sharpshooter or another rogue.  As such, I would generally take crossbow expert and focus on hand crossbows if I were playing one.

Interesting.  The party does include a paladin, so that could work well.  The other three PCs are an evocation wizard, a warlock of the archfey, and an artificer (I don’t know which subclass he intends to take).  Any insights on how those classes might interact with a mastermind?

I can't think of anything particular that would cause them to gain unusual benefit from getting advantage, though it would still benefit them to get it.  It's also possible the player intends to use most of their bonus actions to hide and give themself advantage instead, leaving the benefit from mastermind unused.

Quote from HazelSage >>

I need help.  I’m not new to D&D (four years under my belt), but I have never seen anyone play a Mastermind rogue.  Now, as a new DM, one of my players has selected Mastermind for her future subclass.  I’ve read the description in Xanathar’s several times, and it just doesn’t look that great— but of course, having no practical experience or observations, it’s not unlikely that my impression is wrong. 

Can anyone help me understand how the Mastermind subclass works?  In what kind of situations would it work well?  What are the pros and cons?   Her alignment is True Neutral, if that makes a difference.

so, I choose it personally prob 1/3 time I play rogue.

it works if you are NOT combat optimized.  It looking to do more the int/wis/cha based things in the role play and exploration pillars.

masterminds are a best used at RANGE rogue. Where they bonus action help give their paladin/another rogue advantage from 30 feet away. While peppering things with a bow.

I have also used myself to be up close and personal taking a DODGE actions, and bonus action helping my party members. Only actually attacking in an attack of opportunity or if a very good “sneak attack” chance pops up. (Like if your party member is a grave cleric)

Quote from HazelSage >>

Interesting.  The party does include a paladin, so that could work well.  The other three PCs are an evocation wizard, a warlock of the archfey, and an artificer (I don’t know which subclass he intends to take).  Any insights on how those classes might interact with a mastermind?

 The wizard should still focus buffs and such towards the paladin if not outright doing damage. The artificer is the Tricky one as they might go melee, might go ranged, the warlock you know will want to have some distance for eldritch blast.

the mastermind can essentially bonus action help the paladin to make pretty sure of a hit for a smite that might even be attached to even more spell like wrathful smite/searing/thunderous... giving 2x chance for a crit as well. Which, is quite good as the paladin will do the most damage per individual hit for quite awhile of all the party.

Depending how they play the rogue. They can be a good second tank as the dodge, help, and Attack of opportunity taker. Since the other 3 classes “traditionally” are more ranged based. Additionally, the rogue is the most mobile amongst everyone for the battlefield as well. But this is all for combat.

outside combat, there’s not a negative thing to be said about a mastermind.

To address the pros/cons:

pros: very good at support. Pairs excellent with paladin. Great non-combat in all settings.

con: won’t be the star hero of combat themselves individually typically.

One of the players in the last game I DMed wasn’t playing one, but had played a couple in the past and recommended it to me. As he put it it’s the chess players’ subclass. In combat it is very tactical and most highly effective in campaigns that use battle boards/mats. He was telling me that in his experience it worked best in two kinds of games: particularly small tables and particularly large ones.

The smaller tables of 2-4 PCs tops is apparently a good fit for them as long as the player really focus on teamwork and coordinating their efforts. Like the A-Team, this is the Colonal, they need a B.A. to help in combat, a Face for the Cons, and a Specialist for the magical stuff. If I were thinking of classes for those jobs I would likely consider a Paladin, a Warlock, and an Artificer/Wizard. A smaller party means smaller combats in which the party con focus on coordination and teamwork. It also allows them to take advantage of Misdirection without accidentally finding themselves in a bad spot.

With the larger tables of 7+ PCs there is often so much going on at the same time all over the battlefield that no matter which way the Mastermind goes they will be able to help somebody and there will be lots of opportunities to use Misdirection too.

According to him, simply having the Misdirection feature and tucking close to the right hostile means other enemies will often avoid targeting you to avoid the friendly fire, and if they don’t it might be doing the party’s job. Of course, it’s competing with another Sneak Attack for that Reaction so you have to pick your moments. But as a deterrent it’s worth it. Like I mentioned, the chess players’ subclass. If the smaller party is the A-Team, these larger parties are more like Ocean’s 11 (divided by 2)

He said that in his games the most useful feature was Insightful Manipulator. If the party met with a group of NPCs for a little while and by the end of the parle, his character would be able to tell the whole party what the NPCs mental strengths were, an estimate of their power levels (Goku Style) and lots of times other things as well.

My only personal experience with these is running one as an NPC who is a local Thieves’ Guild leader. That she knew every fact on that list about every one of the PCs was... interesting when it came to negotiations.

Hmm.  Maybe I’ll have her read this thread.  There’s a lot here that I would have a hard time explaining to her; teaching and explanation can be hard for me.  She’s new to D&D, so I’ve been trying to help her out as much as possible, but never having played a rogue myself, I don’t know the mechanics inside and out like I do the rules for other classes.

Quote from IamSposta >>

One of the players in the last game I DMed wasn’t playing one, but had played a couple in the past and recommended it to me. As he put it it’s the chess players’ subclass. In combat it is very tactical and most highly effective in campaigns that use battle boards/mats. He was telling me that in his experience it worked best in two kinds of games: particularly small tables and particularly large ones.

The smaller tables of 2-4 PCs tops is apparently a good fit for them as long as the player really focus on teamwork and coordinating their efforts. Like the A-Team, this is the Colonal, they need a B.A. to help in combat, a Face for the Cons, and a Specialist for the magical stuff. If I were thinking of classes for those jobs I would likely consider a Paladin, a Warlock, and an Artificer/Wizard. A smaller party means smaller combats in which the party con focus on coordination and teamwork. It also allows them to take advantage of Misdirection without accidentally finding themselves in a bad spot.

With the larger tables of 7+ PCs there is often so much going on at the same time all over the battlefield that no matter which way the Mastermind goes they will be able to help somebody and there will be lots of opportunities to use Misdirection too.

According to him, simply having the Misdirection feature and tucking close to the right hostile means other enemies will often avoid targeting you to avoid the friendly fire, and if they don’t it might be doing the party’s job. Of course, it’s competing with another Sneak Attack for that Reaction so you have to pick your moments. But as a deterrent it’s worth it. Like I mentioned, the chess players’ subclass. If the smaller party is the A-Team, these larger parties are more like Ocean’s 11 (divided by 2)

He said that in his games the most useful feature was Insightful Manipulator. If the party met with a group of NPCs for a little while and by the end of the parle, his character would be able to tell the whole party what the NPCs mental strengths were, an estimate of their power levels (Goku Style) and lots of times other things as well.

My only personal experience with these is running one as an NPC who is a local Thieves’ Guild leader. That she knew every fact on that list about every one of the PCs was... interesting when it came to negotiations.

 You worded the “chess player” thing way more eloquently than I did. 👍👌🏻

it’s an underutilized subclass. But it’s very rewarding to play when you have the right conditions.

Quote from HazelSage >>

Interesting.  The party does include a paladin, so that could work well.  The other three PCs are an evocation wizard, a warlock of the archfey, and an artificer (I don’t know which subclass he intends to take).  Any insights on how those classes might interact with a mastermind?

Are any of them elves?  The elven accuracy feat is even stronger with a mastermind in the party.

Mastermind is particularly bad with the wizard - their go-to spells will be save based, which Help doesn't, well, help with.  The warlock will have the easiest time synergising with elven accuracy + nearby mastermind to crit more often.  The paladin will either need to focus on rapiers or dip into hexblade for the e.a. trick, but at that point the Mastermind is doing serious work helping the paladin fish for crits for divine smite.  The Artificer can also synergise, but will want to be an Armorer or Battlesmith so they can make INT-based attacks.

A mastermind is like having an owl familiar on hand with a lot more durability; since the mastermind has to break stealth to do their ranged help, they generally can't help twice while maintaining stealth, so they'll still get swatted if their help is too helpful.  A mastermind spamming help + hide is generally contributing less to the fight than a sneak attack would, no matter what tricks you pull, which is part of why owls don't let you just steamroll every fight. 

There is one elf; unfortunately, they’re the wizard. 🙄  I’ll try to help the rogue (who is new to D&D) by occasionally pointing out situations in which one or another of her skills will shine.  I can also get another of my players to help; he has played a rogue very successfully in the past, and has a spectacular understanding of the rules, without being a rules lawyer.

All of this might be a bit easier if the rogue weren’t my sister.  Don’t get me wrong; she’s great!  It’s just kinda hard to create, much less maintain, an air of authority when your siblings are involved!

Quote from HazelSage >>

There is one elf; unfortunately, they’re the wizard. 🙄  I’ll try to help the rogue (who is new to D&D) by occasionally pointing out situations in which one or another of her skills will shine.  I can also get another of my players to help; he has played a rogue very successfully in the past, and has a spectacular understanding of the rules, without being a rules lawyer.

All of this might be a bit easier if the rogue weren’t my sister.  Don’t get me wrong; she’s great!  It’s just kinda hard to create, much less maintain, an air of authority when your siblings are involved!

I'd ask your sister why she wants to play a Mastermind - what's her actual goal?  Because I'm guessing she wants to be party support and would enjoy playing a bard more.

Actually, it’s become a moot point.  She realized yesterday that her schedule really doesn’t give her the time she needs to play, much less build a character and learn the rules/mechanics.  Thanks to everybody for your help!  If she gets the opportunity to try again, though, this will be very helpful.

Mastermind in a way... is Kind of like Playing Batman to some extent.  Not in the Arkham Saga way (or many other video games for that matter) of punch everything hard as a truck until they all fall down kind of Batman.

But the puzzle solving, Contingency plan for everything, allies everywhere type of Batman that gave him the Reputation for being a Detective that he has.  The Type of Batman you get when he's working with Side Kicks or Allying with other Superheroes.  The One that seems kind of like a Modern Day Sherlock Holmes type.

Or for that Matter. Sherlock Holmes is in some ways a good Example of the Mastermind kind of Rogue when we're getting right down to it.  I don't mean that in snap deductive reasoning about everything. But the way he actively pursues things. Talking and asking questions without giving things away and then moving to the next thing before Authorities or Enemies notice.  Being able to talk somebody into revealing things about themselves that aid him in what he's doing. Disguising himself in ways that even those close to him don't realize it's him when interacting with him.  All those physical parts of what he does in his books to get to be able to have those deductive reasoning moments of his.  Though if they play one with the right feats such as Observant and things like high intelligence and Wits. Then they can certainly Add some of that deductive power in as well.  Because in Essence they are kind of the Work Smarter rather than Harder Rogue.  They'll get their hands dirty but they will do it in the best way that they can to change things up. Even in combat.