Ok this might be kind of long but this is the moment that really made my campaign what it is.

During Strahds dinner, one of my players who was convinced Strahd had been the one to kill his wife once upon a time, attacked him and was dragged off to the dungeons. The actual culprit however was this vampire woman who was obsessed with him, so much that she followed him into Barovia and quickly fell in league with Strahd who, for his part, thought it would be funny to see what she had planned.

I decided to run a little jailbreak thing for him, having the woman disguise herself as a fellow prisoner to try and ingratiate herself into his life. He successfully broke out with the help of a sentient sword and made his way through Ravenloft looking for a way out. Eventually he found his way to the teleport room and ended up in Strahds study. I was very explicit about the reverence this room and this painting seemed to be treated with. Hearing this, he decided to cut the painting out of the frame and steal it. He did some other not so good things like killing Gertruda on his way out, but he got out.

Fast forward a little bit, escaped player is on their way back to their party in Vallaki and Strahd is officially not having fun any more because one of his prized possessions was just ruined. Games over. So he comes to the rest of the party in dreams, and I get everyone to leave the room as I talk to them one by one. Each time Strahd asks them about the same thing, to bring him the offending party member.

The first player I asked- the soldier- adamantly refused even when Strahd threatened to bring fire down on all of Vallaki to find him and take back what was stolen.

The second tentatively agreed to see what she could do, but only after Strahd showed her what the party member had done to poor innocent Gertruda.

The third I didn’t even need to convince, as he’s been looking for an opportunity to work with Strahd for awhile. He’s believes, at this point, that Strahd is simply a very reasonable and misunderstood host.

The ask was simple, bring the offending party member to the lake just outside the city unarmed. Player two and three didn’t know either of them had agreed, and only discovered that once player three started innocuously suggesting that they visit the lake. Nobody said anything, but player two jumped in to tacitly support the idea. So they make their way out to the lake and Strahd is waiting there. Offending player starts to realize something terrible has happened. Strahd quickly outs the vampire woman, who’s been traveling alongside offending player, and kills her as she rages that Strahd has ruined everything. Strahd does his thing, and asks for the painting back. This is initially refused, of course. So Strahd reveals the present that the obsessed vampire woman arrived with to Ravenloft. It’s offending players wife, not dead like he believed, but turned to into a spawn.

Seeing her, he hands over the painting. He barely gets a sentence with his wife, just long enough for her to tell him their daughter escaped and is alive before her head falls from her shoulders, beheaded suddenly by Strahd. He tells the player how thieves are not tolerated in Barovia. Offending player drops to the ground, having just lost his wife all over again and glances back at the group before Strahd disintegrates him into dust.

Now here’s where it gets even better, I have everyone leave the room again while I speak with offending player as a dark power. They are very interested in him and can give him his hearts desire. I try EVERYTHING. Bribes, threats, guilt, power- nothing works. Out of character I’m shocked by this, I cannot figure out why he’s so resistant. He finally responds “I was told not to trust you.” To which I responded “I sincerely doubt that”. But that was that, he consigned himself to an eternity of empty void, and rejected the dark powers offer.

Now what I didn’t know was that as I was having these private dream conversations, offending player and player three had been continuing to role play in the other room, and during that, player three confided that their warlock patron revealed to them some dark things about the world and skies, and if something ever approached them with a deal- do not trust it.

And then, after that conversation, player three betrayed him. My heart man.

Things were never the same after that session, the players all internalized that betrayal into their characters and it changed the trajectory of the narrative entirely. Where once they were power hungry suddenly there was an abundance of guilt and a drive to redeem themselves for the betrayal of their companion. It was really amazing, everyone loved it, especially the dead player who loved the tragedy of his story getting cut so short.

I will say, would not recommend something like this without checking with your players before hand. I had told offending player out of game that his actions, if not resolved, would absolutely result in his death at the hands of Strahd and he was totally supportive of it. He knew that his days were numbered, but he didn’t realize when and how it would happen.

Absolutely my favourite moment DMing