How to Defeat Your Party (Without Killing Them) - Part 1

Our gaming group all started getting heavy into tabletop gaming as a result of 5E Dungeons & Dragons (D&D). We all started with the Starter Set where the players became acclimated with the mechanics by performing public services for Phandalin. Then they became interested with developing their backstories and personalities as they moved onto Princes of Apocalypse where they learned how their actions could leave an impression upon the world. Not long after it was a memorable journey battling and befriending giants in Storm King's Thunder. Though momentary setbacks occurred occasionally, the players started to see themselves as superheroes capable of just about anything with the roll of a die (or several in the case of those who have discovered the 'lucky' feat).

This was all fine and good until I gave them a crash course in original Dungeons & Dragons with the classic B2 - Keep on the Borderlands module. The first session proved deadly and showcased the style and tone of the predecessor to it all. Character death was a certainty. Victory was not assured.

Don't be fooled. This dragon does not care if you have Plot Armor +3.

The fact is that they loved it. Why was this the case? The drama of failure made it more exciting and intense. Suddenly retreating from a suicidal encounter was an attractive option that had not previously been considered. Life was precious and something to cling onto versus the relative comfort of knowing a resurrection spell was just a few thousand gold away. The thrill of risk and reward was instilled in all involved and made playing original D&D an exciting event every time we planned a session.

I had pondered this idea for sometime of how to bring this same type of experience into the modern version of D&D. When our group started playing Tales of the Yawning Portal, a collection of classic D&D modules reworked for 5E, I haphazardly came upon the solution. It wasn't "death" that made the original exciting; it was the prospect of failure that created the environment for a range of emotions that could be felt during a roleplaying game. Anticipation, disappointment, pride, determination, regret, etc. are all things that can only exist if failure is an option that the players believe could happen. In fact, character death was only exciting if there was a prospect of a story to be created from it.

Wiping the party as an exercise in the mortality of characters or to teach the lesson that nothing in the game is a guarantee is, in my view, a terrible way to get the point across. If the party wipes, the game is over. It is not satisfying and does not achieve the same result that 'failure' can provide. Character death can be a driving force to create new possibilities in the story, but only if the Dungeon Master knows how to navigate it in a way that is interesting and creates possibilities that would not have been available otherwise.

My hope is that this will become a regular topic that I can sound off on and share my experiences with. There has been an element of failure that has developed in each of the Yawning Portal adventures I have run and they have all been unique (some spoilers can be expected if you are to continue reading). Some of them were foreseen where I was able to plan for them and others were spontaneous and I had to improvise in order to reframe a party wipe scenario into something that could move the plot along.

#1 - Give the Enemies a Reason to Keep the Players Alive

My experience has been that enemies that toy with the player characters (PCs) and have nefarious intentions other than outright murdering the players tend to be more memorable and give them more cause to develop strong animosities towards them. A good villain has motives that go beyond being super evil and wanting to dominate the world. An even better villain sometimes blackmails or manipulates the players to implicate them in their schemes.

A scenario that took place while playing White Plume Mountain was that the PCs came upon a lair of a mass murdering knight named Sir Bluto and his forsaken crew. As the players entered his guard post I allowed a intelligence (history) check to see if they could identify him from a wanted poster they would have seen plastered all over Neverwinter during a recent visit. Sure enough they were able to recognize him as Sir Bluto, the guilty party wanted for the River of Blood mass-murder case. Their eyes lit up as they heard there was a 10,000gp reward for his capture (alive).

"10,000gp! That's a lot of money! Hey guys, make sure to take care when knocking this guy senseless" said one of the fighters as the party scrambled to get into position for the confrontation that was about to take place. The party was helplessly outnumbered and there was no way they were getting out of the fight without a few casualties. They managed to use non-lethal attacks to bring down the treacherous knight, but it was all in vain as Sir Bluto's eight minions were able to use the party's poor tactical position and their numbers to defeat them.

Party wipe. Could have been the end of the adventure.

Instead, fortune was with the heroes. Sir Bluto's knights were not the type to swear oaths of loyalty unless there was a hefty paycheck involved. Having heard the fighter exclaim the value of Sir Bluto's return to the authorities in Neverwinter, the knights were of a mind to make a deal. After all, they were all criminals too and could easily stroll into town and capture the reward themselves. With the precious magical items of the party and all of their wealth bagged up in a corner of the stone chamber where negotiations commenced, the knights proposed that they would return their belongings if the PCs would take Sir Bluto back to the Halls of Justice to collect the reward and deposit it in a hollowed out tree stump located at an abandoned cottage an hour and a half outside of the city.

There was no better choice that they would be offered, despite their attempts to negotiate. The fact was they had no leverage and this was the best deal they were going to be offered.

They headed to town and did as they were instructed. Though it pained most of them to have 10,000gp in hand that they would not be able to spend, the prospect of losing all their hard earned magical items from their previous adventures was an even tougher pill to swallow. They carried out the task and found the knights to be trustworthy enough to honor their agreement.

This course of events created a story. There was a consequence in that the party did not earn the opportunity to collect on the reward that could have been, and they missed out on the opportunity to take the loot the knights surely had. They also had to make a morally difficult choice in delivering the reward, tax money collected from Neverwinter intended to enact justice for the victims of the River of Blood massacre, to the main instigator's accomplices.

This event did not stop the party from trying to devise ways they could track down the conniving knights and get their revenge. But they soon discovered that the knights had abandoned their previous lair. And every time they started to speak about plans to seek out a diviner to locate them, it seemed an invisible stalker would lash out and put a halt to the conversation. Hmmm...perhaps the thread to a story to take place in another adventure...