Help build Raymond Reddington (sort of)

[Spiritchaser]

Just canvassing for brainstorming ideas at this point. And it’s mostly the personality I think would work... looking for a build that supports that personality, though it’ll obviously be mechanically different than the fictional character


I’m currently playing in an evil (mostly selfish/psychotic) party, and my lawful angry vengeance paladin ends up being too much of a viscous straight man in this company. Oh sure he can do the intimidation thing, and attempt to manipulate fellow players up to a point, but while he can explode into high quality violence with the worst of them, someone with a weaker but still existent code of ethics is going to be more fun here.

The blacklist Reddington manipulates a vast, then small, then bigger criminal network. There’ll be none of that available here, but perhaps magic can suffice.

I was considering trickery cleric, but I don’t see this guy serving a god, unless perhaps deceitfully

Mastermind, or any rogue? I’m just not going to have the information gathering resources, and in this campaign, with this DM, any useful networking is unlikely to exist. EDIT: for clarity, with this DM, IN THIS CAMPAIGN I do not feel that relying on the mastermind feature is wise.

Edit for more clarity and for more history here, in the last 30 years every single shady character we’ve tried to finesse/honourably exchange/bribe/intimidate/blackmail in order to get useful information has backstabbed us, usually sooner than later. I really don’t believe this feature is going to be anything other than painful. I’m ok with that, I just need to do things another way.

Now: contact with ordinary decent folk goes far better. I could perhaps ask if the contacts could be with local law enforcement agencies... not a bad parallel there...

Wizard? Maybe, but I won’t directly have the social skills, and social skills are critical.

Warlock? Perhaps

Bard? I DO NOT PLAY an instrument. Otherwise whispers might be ok. But... I DO NOT PLAY AN INSTRUMENT. Sword or valor might be ok.

Divine soul necrosorcerer? Actually not a crazy idea.

At this point I’m mostly just looking for wild and crazy ideas to tie together into something.

Any and all suggestions appreciated!

Edit: NO PHB +1 rule to worry about, no UA without special approval, which in this context probably means no UA, start at level 4, probably go to 15 or so

[moonfly7]

Mastermind rogue, it actually grants you a criminal network like thing. Add that to the criminal backgrounds criminal contact and you have decent stuff.

[Spiritchaser]

Mastermind rogue, it actually grants you a criminal network like thing. Add that to the criminal backgrounds criminal contact and you have decent stuff.

Criminal network would be great, but I know that with this DM, in this campaign that feature will be either severely limited, painful to use, or most likely, actively treacherous. As such, I do not feel that mastermind is remotely wise.

I’m going to have to simulate this with magic.

[Vogie]

I would use the 2-5 levels of Enchantment Wizard, and the rest is Mastermind Rogue. That Hypnotic Gaze mechanic displays Red's ability to take on an a single target, and talk them into submission. He's well equipped with rituals, and largely noncombat techno-magic (message, hold person, sending, Tongues, Charm Person, Mage Armor, et cetera).

While he will be a charismatic individual, he's smarter than he is persuasive or intimidating... that's largely due to the Friends cantrip and Charm Person giving him advantage on his charisma checks. He's not dominating, he's convincing. Just convincing enough, for just the right moment.

I'd build a custom background with proficiencies in Persuasion and perhaps Slight of Hand, and use the Criminal Contacts feature or something similar to round it out... maybe a derivation of the Noble background. He'll probably lean towards an Feat like Prodigy or Skilled rather than ASIs.