Lets Build a Spy/Saboteur!

[Nagog]

I'm soon joining a campaign with the premise of a fantasy world with a similar political climate to our world in the year or two preceding World War 2, with the key difference (ya know besides magic and a plethora of races and such) being that there really isn't one side that is distinctly evil. Political opinions aside, what would be a good build for a spy/saboteur? I plan for my character to be downright evil and trying to get war to break, so being able to manipulate folks would be a great bonus.

[nickl_2000]

Assassin Rogue
Mastermind Rogue
Or probably the best: Whispers Bard.

[darknite]

Expertise in Deception and Stealth at first; Perception and Stealth later. Thieves' tools and disguise kit proficiency along with Performance skill and Actor feats allows for infiltration. Spells like Disguise Self, Detect Thoughts, Comprehend Languages, Tongues, Detect Magic, Find Familiar, etc.

[Man_Over_Game]

There's a few ways you could do it.

Mastermind Rogue is an expert at magical disguises and skills.
A Warlock of any kind can pick up Mask of Many Faces to look like anyone of your choosing. You could pick Tome + Rituals for more solutions to your problems, or summon an familiar to be your lookout.
Bards would also do well, with a Lore Bard having multiple skills to solve problems with, Glamour being good for distractions, and Whispers for being an infiltration specialist.
Lastly, a Sorcerer with Subtle Spell could wreck a lot of havoc.

So, based on priority, here's how I'd order them:

MANIPULATION
Warlock (Chain + MoMM)
Warlock (Tome + MoMM)
Whispers Bard
Glamour Bard
Mastermind
Sorcerer
Lore Bard
Assassin Rogue
PROBLEM SOLVING



SOLO
Assassin Rogue
Whispers Bard
Warlock (Chain)
Warlock (Tome)
Sorcerer
Lore Bard
Mastermind Rogue
Glamour Bard
TEAMWORK

[Corran]

I'm soon joining a campaign with the premise of a fantasy world with a similar political climate to our world in the year or two preceding World War 2, with the key difference (ya know besides magic and a plethora of races and such) being that there really isn't one side that is distinctly evil. Political opinions aside, what would be a good build for a spy/saboteur? I plan for my character to be downright evil and trying to get war to break, so being able to manipulate folks would be a great bonus.
This is just an idea, but this setting is a good opportunity to do sth more rare than just playing the classic evil backstabbing snitch. Play a non-evil spy. One nation's traitors are another nation's heroes and all that. Play someone respected, who tries to be above suspicion (soldier/noble/folk hero/etc background helps here), and who generally tries to do good and help people, not just for pretend. But because he is a good person, who believes that his side is in the right and if it wins the possible coming war then it will be better for everyone. Lying spying and betraying people's trust is dishonest, but you are doing it for the greater good, and in your character's mind that might be the mark of the true hero. There is the possibility of conflict too. Having a soft spot for your misguided ''friends'' might put you into some trouble with your puppet master. And vice versa, this could lead to some interesting rp if any of your friends come to suspect you and/or find out.

[Mercurias]

I would personally love to play a Tiefling Chain Warlock with the Fiend Patron for this kind of setting.

I would probably pick up the Actor feat as well as the Spell Sniper feat.

For Invocations, I would start out with Mask of Many Faces, then add in Pact of Chain Master, Agonizing Blast, Repelling Blast, and lastly Eldritch Spear.

Put together, you'll have a talented spy with plenty of options for skullduggery and assassination. An invisible Familiar that you can speak through does wonders for information gathering and clandestine meetings. You'll also be an unholy terror on anyone making a public speech if you can snipe them off of their podiums while in disguise and then slip away in the confusion. By level 14, you'll be able to blast someone directly into Hell from two football fields away.

[Nagog]

This is just an idea, but this setting is a good opportunity to do sth more rare than just playing the classic evil backstabbing snitch. Play a non-evil spy. One nation's traitors are another nation's heroes and all that. Play someone respected, who tries to be above suspicion (soldier/noble/folk hero/etc background helps here), and who generally tries to do good and help people, not just for pretend. But because he is a good person, who believes that his side is in the right and if it wins the possible coming war then it will be better for everyone. Lying spying and betraying people's trust is dishonest, but you are doing it for the greater good, and in your character's mind that might be the mark of the true hero. There is the possibility of conflict too. Having a soft spot for your misguided ''friends'' might put you into some trouble with your puppet master. And vice versa, this could lead to some interesting rp if any of your friends come to suspect you and/or find out.

The DM has made it known to me that this world is entirely that premise, with both sides of the war being "Good" and the party needing to decide which side to take for ourselves. I'm posing as a researcher/spy for one of the sides, when in reality I'm spurring the war on as to essentially do what Achilles does in Shadow of the Hegemon. If you haven't read it, essentially he betrays one side after another and uses the war to always come out on the winning side, and with more power than he previously had, in a long-winded plot to rule the world himself, therefore creating world peace. So he is striving for world peace, but in his own twisted way.

[stoutstien]

I'm soon joining a campaign with the premise of a fantasy world with a similar political climate to our world in the year or two preceding World War 2, with the key difference (ya know besides magic and a plethora of races and such) being that there really isn't one side that is distinctly evil. Political opinions aside, what would be a good build for a spy/saboteur? I plan for my character to be downright evil and trying to get war to break, so being able to manipulate folks would be a great bonus.
UA allowed? The artificer is a perfect fit for sabatoge. Bonus if you call him max Maximus

[Naanomi]

Yuan-Ti... Poison food, eat it anyways, watch your enemies fall

Also, in the mechanical sense... Cutting Words on people trying to see through your Disguise has more practical value than many of the other comparable abilities

[Corran]

The DM has made it known to me that this world is entirely that premise, with both sides of the war being "Good" and the party needing to decide which side to take for ourselves. I'm posing as a researcher/spy for one of the sides, when in reality I'm spurring the war on as to essentially do what Achilles does in Shadow of the Hegemon. If you haven't read it, essentially he betrays one side after another and uses the war to always come out on the winning side, and with more power than he previously had, in a long-winded plot to rule the world himself, therefore creating world peace. So he is striving for world peace, but in his own twisted way.
Fair enough.

Find a good way to relay information. This can be easily achieved by mundane means if you can work it out with the DM (taking sth like the spy background certainly helps), but if you plan on playing a caster, look for spells like sending and dream (looking at another thread, chainlock with pact of the chain master would work well here). If you send letters because you lack high level magic, sth like illusory script could be useful; or the keen mind feat; isn't that the one that allows you to write in code? Or ask the DM if you can spend a language (or refluff sth like druidic or thieves' cant as spy code).

As far as spying on people goes, you will need things like stealth, thieves' tools, perception (observant for read lips helps here). Expertise helps here. If you go with a caster, look at spells like clairvoyance, arcane eye, scrying, and other divinations.

For impersonating/disguises, look at stuff like disguise self (actor feat helps here), alter self, etc, though you could also look at playing a changeling.

High deception and persuasion would be very useful. If UA is allowed, look at the diplomacer (or whatever its name is) feat. This is mostly rp and having good numbers on the appropriate skills, but if you play a caster, things like charm person and the like all help here, for creating allies (even temporary ones).

All in all, I think any type of rogue (masterminds at late levels), trickery cleric, any druid (assuming you can justify it), sorcerer with subtle, warlock (with emphasis on goolocks) and any wizard, all of these classes would be good. Oh, and bards, of course.

If you want strong surprise rounds... well, that's a whole other story. Unless you plan on doing plenty of stuff off screen, it's not worth it.

I think I'd go with a changeling goolock with pact of the chain (possibly with 1 or 2 levels in rogue, for stuff like expertise and thieves' cant; though it's hard to postpone stuff like scrying, create thrall, etc). Though, the best way to play a successful spy character imo, is to convince the DM and the other players to go along. If they find your character concept fun and/or intriguing, everything will roll a lot more smoothly (I cannot emphasize this last part enough). Talk it over and be open minded and listen to suggestions (in the end decide what you want, it's your character).
My first 5e character was a spy. The setting was basically one kingdom and there were some little info about the neighboring rival nation. Not much to work with. There was no war, but DM agreed to the idea that there were tensions that had slowly started developing into a cold war-ish state of things. When I told the other players that I planned to play a spy for the rival nation that was off screen, one of them came up with the idea that since his character was a member of the royal family (sth like 15th in the line for the throne), my character could have approached his for the purposes of befriending him and getting access to sensitive info. As the characters achieved quests/etc, and their fame grew, the more respected the noble character would become and the more access to information he would have; information that my character would be stealing. Then I came up with the idea. ''Hey, you character is noble and he can pull some strings, so could he influence things so that my character gets promoted?'' (she was working for the military). So, once again, the more glorious things my character did with the party, the more close she was to another promotion, and another, and another. She was planning to go as high as possible, so that she could do maximum damage when the time was right. That allowed me to roleplay ambition (even if it was ambition only in a guise). Some sessions in, and a third pc was approached by npc's working for counterespionage who tasked him secretly at keeping an eye on my character and the noble character, because they had started suspecting of sth (and here is the thing; when this third player had his pc tasked to do this, he didn't jump at the opportunity of playing detective; instead, he had his pc undertake the task with extreme reluctance -he basically had to, cause he was in a tough spot- since his character was not suspecting and was fidning it very difficult to believe that could be true; have buy-in from others for your concept, it will help!). And these stuff were all on the side, just for spicing things a bit. It works much better the more involved everyone else is at sth. Making your character's motivation sth that others can share in and be part of the fun (instead of having it look like a competition of some kind; or worse, sth no one is interested in), will make that all the more enjoying for you too.

[Warlush]

I love the Great Old One's telepathy for messing with people's heads. So probably my favorite combo it GOOlock 3/Lore Bard/X. Pact of the chain. Plently of slots for Disguise Self so no need for MOMF. Or go warlock all the way to 14 to have a permanently charmed humaniod. You can also get the invocation that allows you to see through walls.

[wilhelmdubdub]

BACKGROUND
urban bounty hunter for ear to the ground

Whispers bard

skill feat: diplomat

[Nagog]

Ok, I think I know what I'm going to use thus far. The DM has recently let me know that a common setting is a city with magic dampening materials used in it's construction, so that puts a bit of a damper on my subterfuge options. But here is my semi-finished product:
Rogue 1/Warlock 4
Actor Feat
Hexblade Patron (for the inevitable combat, as there doesn't seem to be a combat heavy character in the party yet)
Book of Ancient Secrets
Mask of Many Faces Invocation

I hope to use the Mask of Many Faces and the spell Friends to build contention between allies, then, if possible, use Hex to grant the impersonated individual disadvantage on persuasion checks to convince their former allies that there has been some misunderstanding somewhere. I'll also get the invocation so that I no longer have to sleep (paranoia as well as light activity may be able to include some subterfuge while the party is not present), and once the subterfuge build is complete, I'll work on getting Eldritch Spear and Spell Sniper to combine with Mask of Many Faces to cause a scene either assassinating somebody or making an assassination attempt (failing intentionally) while in the guise of an enemy soldier/officer. Actor feat and expertise in deception should produce a greater facade as well.

[Man_Over_Game]

Ok, I think I know what I'm going to use thus far. The DM has recently let me know that a common setting is a city with magic dampening materials used in it's construction, so that puts a bit of a damper on my subterfuge options. But here is my semi-finished product:
Rogue 1/Warlock 4
Actor Feat
Hexblade Patron (for the inevitable combat, as there doesn't seem to be a combat heavy character in the party yet)
Book of Ancient Secrets
Mask of Many Faces Invocation

I hope to use the Mask of Many Faces and the spell Friends to build contention between allies, then, if possible, use Hex to grant the impersonated individual disadvantage on persuasion checks to convince their former allies that there has been some misunderstanding somewhere. I'll also get the invocation so that I no longer have to sleep (paranoia as well as light activity may be able to include some subterfuge while the party is not present), and once the subterfuge build is complete, I'll work on getting Eldritch Spear and Spell Sniper to combine with Mask of Many Faces to cause a scene either assassinating somebody or making an assassination attempt (failing intentionally) while in the guise of an enemy soldier/officer. Actor feat and expertise in deception should produce a greater facade as well.

I used to run the same exact thing. It was probably my favorite character of all time, and I suspect you'll have an awesome time with it.