>Trusted recurring NPC that appeared to be aiding the party

>>53874843
It's only a dick move if you don't give players room for doubt.

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>>53874843
This reminded me of this story.

>>53874843
that depends entirely on whether they saw it coming or not

If its a member of the opposite sex of the majority of the party, they should have seen it coming.

>>53874843
Had a Harper informant that was a long-term Zhent double agent that had the PC's further Zhent Aims unwittingly multiple times until they caught on after they killed a harper meeting and ended up Geassed by Big E over the misunderstanding, they only saw said person when he was spending his earnings in a titty bar bragging about fucking them over.

Suffice to stay, the Scarlet Tickle earned it's name for a new reason that day.

Also, I once had a baboon-man creepy witch docotor wise man that was actually one of Demogorgon's halves guide the PC's for a while.

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>>53874843
As a player I always encourage DMs to play dirty - as I player, I always do and many STs have trouble keeping up with me.

As for your example, if I was a player I would have investigated the NPC just as a matter of course. So long as the NPC has always been the same secret bad guy, and so long as you tried your best to make sure they could find out if they wanted to, dm is doing their job just right.

>>53875308
>>53874843
Our DM accidentally had a trusted NPC refer to another NPC he was referencing say "him" instead of "her" in one conversation during a throwaway encounter. He didn't expect anyone to catch it, but I did.

We called the traitor out after some planning and trickery and completely shifted the direction of the campaign, negating like 4 painstakingly crafted boss fights and like 2 weeks of planning on his part.

We all loved that he gave us the option to do that and it made the campaign so much better.

>>53874843
>BBEG

Ugh.

>>53875662
>Ugh

BBEG.

>>53874843
Have his subtly backstabbing them at every turn. If they bothered to investigate him, it'd be pretty obvious.
Why do the bad guys always know where our hideouts are?
Why do the bad guys always know where we're going?
Why do the bad guys know my one weakness?
Why is this dude always suggesting we split up?
Who is this dude on the phone with every night that he doesn't want us to hear his conversation?

Depending on the intelligence of your players, of course. I've dropped hints that seemed way too obvious that it took my players hours to figure out.

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>>53875591
This is what im talking about, man. Take the kid gloves off, trust your dm, and trust your players back. Sometimes your plans get fucked as a DM, but that's just part of the fun.

(They can get the players back later with some plot they don't manage to catch.)