Creating a Spymaster character

[Slipjig]

Hi all!

I'm getting back into P&P for the first time in forever, and I'm looking for a little help on realizing my character concept. My character concept is a spymaster. I'm looking for a character who would prefer to recruit and works through agents, but is capable of handling things himself when needed, both in terms of sneaking in and throwing down when needed.

The party already has a rogue, so I was thinking Shadow Monk. That could give me a reasonable infiltration capability while also meaning that I don't have to worry about needing to conceal armor or weapons. My main concern is that the primary stats I see being key to my concept are INT and (to a lesser extent) CHA, but neither of those are key Monk stats.

I'm willing to sacrifice optimization for flavor, but I don't want to build a character who can never pull his own weight to the point that he'll be a drag on the party. Any suggestions? As I said, I'm new to 5e, so I'd appreciate it of you could tell me where to reference specific options.

[Sorinth]

Bards make great spies/spymaster.

That said Shadow Monk can work as well. Using Custom Lineage or V. Human and taking Skill Expert should do the trick, you'll have plenty of skills, and Expertise (I'd probably go Deception). You can always also start Rogue and then multi-class out in Shadow Monk.

[Fatefulforce]

Hi all!

I'm getting back into P&P for the first time in forever, and I'm looking for a little help on realizing my character concept. My character concept is a spymaster. I'm looking for a character who would prefer to recruit and works through agents, but is capable of handling things himself when needed, both in terms of sneaking in and throwing down when needed.

The party already has a rogue, so I was thinking Shadow Monk. That could give me a reasonable infiltration capability while also meaning that I don't have to worry about needing to conceal armor or weapons. My main concern is that the primary stats I see being key to my concept are INT and (to a lesser extent) CHA, but neither of those are key Monk stats.

I'm willing to sacrifice optimization for flavor, but I don't want to build a character who can never pull his own weight to the point that he'll be a drag on the party. Any suggestions? As I said, I'm new to 5e, so I'd appreciate it of you could tell me where to reference specific options.

Bards can work for you as well.
They have all the right tools to simulate a rogue.

They get expertise just a little later than the rogue as well as spells like disguise self that can help you achieve what you need.

Then depending on your college, you get added features. Glamour bards are fantastic for "charming" with enthralling performance so you can extract information that fits in really well with what you are trying to do.

The beauty of Enthralling performance is if a target fails they don't know you were trying to charm them.


College of Whispers can work very well as well. At lvl 6 you get mantle of whispers It can work very well for infiltration missions

Another nice way to achieve what you want is mixing in feats with backgrounds if you are set on a particular class but want the flavor you are after without being pigeonholed to a class like rogue/bard

Backgrounds

City watch/investigator: for investigation/insight skills
Criminal/spy: for thieves tools and deception/stealth
Faceless : for disguise kit, deception/intimidation
Urban bountyhunter: thieves tools, deception/insight/stealth/persuation
Entertainer/gladiator: disguise kit, perfromance
Charlatan: Disguise kit, forgery kit, deception, and sleight of hand
Urchin: Disguise kit, Thieves tools, Sleight of hand and Stealth
Celebrity Adventurer's scion: Disguise Kit, Perception, Performance

Feats
Prodigy: Gives you any 2 skills plus expertise in a skill you are proficient in plus a tool kit like thieves tools/disguise kit/forgery kit.
Skilled: gives you access to any 3 skills/tools. So this one is really nice
Skill expert: 1 skill plus 1 expertise
Skulker: allows for you to hide in dim light

[LudicSavant]

Hi all!

I'm getting back into P&P for the first time in forever, and I'm looking for a little help on realizing my character concept. My character concept is a spymaster. I'm looking for a character who would prefer to recruit and works through agents, but is capable of handling things himself when needed, both in terms of sneaking in and throwing down when needed.

The party already has a rogue, so I was thinking Shadow Monk. That could give me a reasonable infiltration capability while also meaning that I don't have to worry about needing to conceal armor or weapons. My main concern is that the primary stats I see being key to my concept are INT and (to a lesser extent) CHA, but neither of those are key Monk stats.

I'm willing to sacrifice optimization for flavor, but I don't want to build a character who can never pull his own weight to the point that he'll be a drag on the party. Any suggestions? As I said, I'm new to 5e, so I'd appreciate it of you could tell me where to reference specific options.

Shadow Monk is good at making the whole party stealthy, because of Pass Without Trace (among other things). But every spellcaster can get Pass Without Trace, even if it's not normally on their spell list, by taking Mark of Shadows, Mark of Passage, or the Dimir background.

If you want to be Int-based, then you want Arcane Trickster, Eldritch Knight, Wizard, or Artificer. All of these can be made into very effective stealthy spymaster types with proper optimization.

Arcane Trickster is pretty much exactly what you'd expect (and arguably the strongest Rogue subclass), but by no means should you think that you have to be a Rogue to do this sort of thing (and do it extremely well, possibly even better than Rogues).

For a Wizard, you'll have aaaaall kinds of magics that help you infiltrate or spy. You can seriously be any subclass, though some particularly relevant subclasses include Diviner (for Matryoshka Doll spell slots on spying divinations, or guaranteeing failed saves on info-gathering spells, or helping/foiling skill checks, the like) and Enchanter (Alter Memories has serious implications for spycraft). Use your magic to remotely keep in touch with your contacts, report back to your bosses, divine information on your foes, disguise yourself, read minds, and so on and so forth. If you want to be the best at working through agents, a well-played Wizard has more support to offer than any martial.

Dex Eldritch Knights (https://forums.giantitp.com/showsinglepost.php?p=24681222&postcount=523) can be super stealthy (even moreso with Mark of Shadows (https://forums.giantitp.com/showsinglepost.php?p=24682452&postcount=530)) and can summon all of their weapons and armor (or tank in no armor at all); perfect for having to throw down in the middle of a noble gala or something. There's no weapons to conceal, because you don't need to carry any. And you can combine a deadlier alpha strike than an Assassin Rogue with being a lockdown tank.

All of the above can get proficiency in whatever skills you like, you don't need to fuss over that in 5e (just use the Custom Background option and pick whatever you want. It's not even a variant or anything, it's default).

[Ogun]

Just an idea:
Artificer for find familier, tiny servants , Homunculus Servant, lock picking, Int to attacks ,decent armor.

[Naanomi]

Warlock works good for a 'behind the scenes' kind of guy... Social, use your super familiar as your voice/field agent, etc... Aberrant Mind can function similarly with subtle mental sneakiness

For more of a plotter/planner one could always go Wizard... Diviner, Illusionist, Enchanter...

[Damon_Tor]

The party already has a rogue, so I was thinking Shadow Monk. That could give me a reasonable infiltration capability while also meaning that I don't have to worry about needing to conceal armor or weapons. My main concern is that the primary stats I see being key to my concept are INT and (to a lesser extent) CHA, but neither of those are key Monk stats.

Masterminds are basically rogues designed to work well with other rogues, which sounds exactly like what you're looking for.

[Sigreid]

Enchanter wizard. Eventually you can make them forget you were ever giving the orders.

Maybe Old Ones warlock? Thrall could make it easier.

[Chronic]

Sorcerer, what else? They have access to subtle spell which make them the best stealth caster in the game. And the best subclass for it is aberrant mind. I mean undetectable spellcasting, mind reading, telepathy and a ton of charisma to back it up, what's not to love?

[Unoriginal]

To me being a Spymaster would mostly be represented through the PC's Background. And classe can be a spy, even Barbarian.

[Kvess]

If you want to be a spymaster, have you put any thought into the organization you are spying for? Is it a kingdom, a church hierarchy, a guild or a secret society? That could influence whether your spymaster is a commanding officer, a priest, someone connected to organized crime, or the leader of a cell for a more decentralized organization like the Harpers or Zhentarim.

I agree with Unoriginal that you don’t need to play a particular class to be a spymaster, but narrowing down the organization you work for could help you make other choices.

[Man_Over_Game]

Bard has my vote, specifically because of how Bardic Inspiration works.

See, a Spymaster works by using information. He's not a tactician. He doesn't give commanding orders to people. He tells you something and that something helps you fulfill your mission later on down the line.

So what we're looking for is some kind of delayed gratification.

Mastermind's out for this reason. Battlemaster's out. The longest-lasting, non-spell buff that I can find that can be related to providing information is Bardic Inspiration, which lasts 10 minutes. Not much, but it's what we got.

So if Bardic Inspiration is the solution, we probably want something that leans heavily into that kind of playstyle, where you are good at Bardic Inspiration's normal use.

So.....Eloquence Bard?

After rereading the subclass features, I realized that every single one of those features are things that easily translate into a Spymaster. Other options can be interpreted as being a Spymaster, but Eloquence has to do very little translating or settling to get there. You aren't an Eloquence Bard that has a Spymaster theme plastered over it, you're playing as something that plays as close as the game gets to a Spymaster.

TBH, the only other things I think could put up a competition are things that would make you a better spy, like Mask of Many Faces as a Warlock, or your aforementioned Shadow Monk, in case you're comfortable not having any of your abilities actually refer to the "Spymaster" concept and are content with separating your RP with your mechanics.

[Verble]

My first recommendation is an Eloquence Bard. My second is an Abberant Mind Sorcerer for those epic subtle mind control spells. Two levels of warlock might not be bad with access to at will disguise self and the friends cantrips. That could also be done by taking the feat that grants you an Invocation.

It depends how important being in melee is to your concept, and how much magic you want.

I had a shadow monk I played (Kobold) and while he was stealthy he was also pretty squishy. Teleporting and running up walls was pretty cool. Though his charisma and intelligence was quite low.

Alternatively,

I have a character in the works who is a propagandist for the Dragon Empire who just so happened to get exiled because there were rumors his bloodline is not pure(as indicated by his Abberant magic). He was an assistant in a noble Dragon household working as spy and fancy tailor(inspired a bit by Garrak in DS9).

Starting first level as an aberrant soul sorcerer gives him lots of cantrips(and there are some super cool dragon cantrips in the Midgard book), and access to some great spells, and proficiency in Con saves for concentration. His race is dragonkin, a homebrew race by my DM.

Dragonkin cantrip
Pummelstone -60 ft
Make a ranged spell attack as you create and hurl a chunk of stone. On a hit deal 1d6 bludgeoning and must roll a d4 when it makes an attack roll or ability check during it's next turn, subtracting the result of the d4 from the attack or check roll

Sorc cantrip
Puff of smoke(Midgard) 30ft
Bonus action
Dex save or be blinded until the start of your next turn.

Dragon's roar(Midgard) 30ft
Charisma saving throw or take 1d4 psychic and is frightened of you until the start of your next turn. A target can only be affected by your dragon roar once per 24 hours

Mind sliver -sorc additional
Intelligence saving throw or the target takes 1d6 psychic damage, and the first time it makes a saving throw before the end of your next turn, it must roll a d4 and subtract the number rolled from the save.

Mold Earth Cantrip

Mage Hand cantrip

Sorc first level
Arms of Hadar*
Dissonant Whispers*
Shield
Absorb elements

Bard cantrip
Minor illusion
Prestidigitation

Bard first level
Bane
Command
Tasha's Hideous Laughter
Healing Word

For skills he has
Persuasion -from race
Deception, arcana - sorc
Perception, history - background
Insight - bard

So he's a great face character with debuff and control spells. I'd probably go overkill on the social skills and take expertise in deception and persuasion so my rolls will always be super high. His initial background was from the Midgard source book but I've tweaked it a bit and trade bonus languages for thieves tools and tailors tools.

You end up with a type of spy agent, and a bard without the performance skill or vicious mockery cantrip(as his racial bonus cantrip was too similar).


For a focus on warlock you can make a pretty great jack of all trades with a celestial warlock of the tome. So you can ranged blast with Eldritch Blast, melee with Shillelagh and booming blade, gain silent image or disguise self at will, and use your spell slots to buff or control. With the celestial healing light ability you get multiple dice you can use to heal as a bonus action. This works nicely if a character has gone down you can heal them(bonus action but NOT a spell) then use Polymorph them into a T-Rex for a fun turn around.

[Xetheral]

Great Old One Warlock gets Sending twice per short rest starting at 5th level. If you're an Elf you can long rest in four hours instead of eight. So an Elf Great Old One Warlock gets at least 8 Sendings per day to communicate with your agents while your allies finish their long rests....

[loki_ragnarock]

Soulknife.

You don't fail, you are always armed, and you can keep tabs on your contacts and facilitate their communication while sitting in a café a district or two over from whatever's actually going down.

Bard is likewise good. Jack of All trades lets you actually behave as someone who's pretty okay at doing stuff even when you shouldn't have any idea what you're doing. Posing as a carpenter? Jack of All Trades! Posing as a coiffeur? Jack of All Trades! Sort of know what you're doing even when you have no idea what you're doing!
Only way I can think of to add proficiency to your "Manage Subordinates" ability checks.

[Sorinth]

Soulknife.

You don't fail, you are always armed, and you can keep tabs on your contacts and facilitate their communication while sitting in a café a district or two over from whatever's actually going down.

Bard is likewise good. Jack of All trades lets you actually behave as someone who's pretty okay at doing stuff even when you shouldn't have any idea what you're doing. Posing as a carpenter? Jack of All Trades! Posing as a coiffeur? Jack of All Trades! Sort of know what you're doing even when you have no idea what you're doing!
Only way I can think of to add proficiency to your "Manage Subordinates" ability checks.

I hadn't thought of Soulknife but it's pretty solid. Untraceable communication is always great, and spending the psi dice on ability checks is always useful for a spymaster since they have so many skills they need to be good at.

[loki_ragnarock]

I hadn't thought of Soulknife but it's pretty solid. Untraceable communication is always great, and spending the psi dice on ability checks is always useful for a spymaster since they have so many skills they need to be good at.

When I first pitched it, I was thinking that you'd have a few key subordinates that you could keep tabs on via psychic whispers... but there's no language in the ability that indicates you can't have multiple of these bondings running concurrently.

So at third level you could have... one free use, four psi-die, so 10 people working for you and constantly reporting back for a few hours a day, if you needed to stretch?
If each one is leading a four man team, that's 40 spies you could ultimately be coordinating with every day from the safety of Le Café Tournon? Place yourself centrally in whatever city and you could probably cover most of it, unless it's truly massive like the nine square miles of old Constantinople or something. Even then, you could probably keep tabs and get updates by establishing the bond and just going for a walk about; all people know while observing you is that you go for a walk at the same time every day after a morning meeting with your key subordinates.

As this is all proficiency based, you could go as far as 3rd level Soul Knife/ Whatever else and be able to coordinate truly massive undertakings. I don't know that simulating constant Zoom meetings is everyone's cup of tea, but as far as management sims go...


So, something like Half-Elf Soul Knife 3/Knowledge Cleric 2/Lore Bard X?

Half-Elf nets you two skill proficiencies and a broad enough ability base to make the multi-class work. Knowledge Cleric 1 would give you more skill proficiencies and expertise, namely the knowing things proficiencies. Knowledge Cleric 2 would give you a Channel Divinity to gain proficiency in whatever you needed in the moment, opening up synergy with Psi-Bolstered Knack. Lore Bard would net you more skills and expertise, the ability to "delegate" via bardic inspiration, and access to a host of spells that complete the package.
By level 10, you could be running contact with as many as 144 spies a day (assuming one man in a 4 man team as relay). You'd have proficiency in (2 race + 2 background + 4 rogue + 2 knowledge cleric + 1 bard multiclass + 3 Lore Bard) 14 skills and expertise in six of them, a floating per short rest proficiency in whatever you like, and the ability to perform as a brewer/musician/carpenter/blacksmith/etc with the same level of competence as any first level character. For people engaged in something more critical, your walk can take you near them where you spend a minute doling out all of your bardic inspirations and maybe casting a buff spell or two (like Longstrider or Invisibility for infiltration, or Shield of Faith for a smash and grab) before meandering off to an hour long martini lunch, where you recharge your ability to do it again for the mission critical evening mission.

With point buy, you could wind up with a S:8 D:14 C:11 I:14 W:14 Cha:16. You don't get an ASI until 9th level. But that's okay. You don't have to be great at anything; you have people for that. And frankly, you are kinda great at many things, even with lower stats, thanks to a combination of wide expertise and psi-bolstered knack. You'll never be Rambo, but that's okay because you employ a couple of rando Rambos who take care of the action scenes as agents. You aren't on the scene at all. You. Are. The. Director.
And you, Director Rick Furor, run this city.

[Slipjig]

Wow, that's amazing. I absolutely love it for an NPC, but I'm not sure how well it would integrate with a more standard batch of PCs. It would make for awesome downtime narrative, but I'm not sure I'd be able to pull my own weight when it came time to actually run a dungeon.

There have been a lot of great suggestions in the thread, thank you everybody!

[loki_ragnarock]

Wow, that's amazing. I absolutely love it for an NPC, but I'm not sure how well it would integrate with a more standard batch of PCs. It would make for awesome downtime narrative, but I'm not sure I'd be able to pull my own weight when it came time to actually run a dungeon.


In the event that you, Director Rick Furor, had to actually get your own hands dirty, you'd probably be keeping the outside calls to a minimum.

In a dungeon you'd:
Find and disarm mundane traps (thieves tool proficiency, investigation) Level 1 onwards
Find and disarm magical traps (arcana proficiency (and likely expertise)) Level 4 onwards
Draw upon your knowledge to give context (other knowledge skills) Level 1 maybe, level 4 certainly
Spot ambushes (perception proficiency) Level 1 onwards
Find secret doors (investigation) Level 1 onwards
Light the way (light cantrip) Level 4 onwards
Facilitate party stealth (psychic whispers for perfectly silent coordination) Level 3 onwards
Point out the maiden standing in the summoning circle might not be on the up and up (arcana, insight) level 4 onwards

You'd basically be doing the typical rogue angle stuff, just... with a level of extreme competence that exceeds what someone of your level should really be capable of, thanks to psychic knack. Failure sort of isn't in the cards; you do disarm that trap, you do spot that secret door, you do find the false bottom on that chest, you do recollect a historical tidbit that gives greater context to this text you've found, you do get a sense of the value of this captive goblin's word. This part of it only gets better and better with time as you draw more and more skills under your belt.

In a fight you'd:
Throw daggers or use a bow to stay out of melee and deliver sneak attacks level 1
Use your superior mobility to stay at range (cunning action) level 2 onwards
Use your special pew-pew to stay at range even better (psychic blades) level 3 onwards
Buff allies while using superior mobility to maintain concentration (shield of faith, bless, guidance, later bardic inspiration) Level 4 onwards
Pop up healing your heavy should things go poorly (cure wounds with cunning action) level 4 onwards

You'd basically be doing typical rogue angle stuff for the first few levels, switching over to a mobile support platform with some light fire support, ultimately transitioning to full mobile support. The frantically scrambling to stay out of melee thing will be consistent throughout, however. The barbarian or fighter is going to have to run the show come melee time. Let Captain Amn Erica and the Inconsolable Sulk take the hits; that's what you assembled them for at the end of all those post credits scenes, anyway.

If you're genuinely worried about it, using Tasha's floating racial ASIs could let you swap your starting dex and cha scores; most of the build would be essentially the same, except you'd have a slightly higher AC, to hit, and initiative during those early levels. You'd still be vulnerable by yourself, but what adventurer isn't? You wouldn't be a contender for DPR... but again, that's why you recruited Captain Amn Erica and Ferrous Fella to begin with. Ebon Recluse - your normal point of contact - probably had a sick day or something, but you can do most of the things she can do anyway.

So no worries; when you go to sack the Yuan-ti Temple with The Vendetta, you'll be perfectly capable of shouting, "I've had it with these motherflipping snakes on this motherflipping plane of existence."

[XmonkTad]

There have been a lot of great suggestions in this thread already. Especially loki_ragnarock's Soulknife multi class. I would like to give special mention to the Swashbuckler's level 9 ability Panache that lets them charm someone in a non-magical way and that doesn't make them hostile at the end of the charm. Also, it has no limitations on usage so even though it only lasts one minute you can refresh it as necessary.