I've been building up a villain in my campaign, so far with good results, but now I'm struggling to find a way to pull off his most heinous deed.

The idea is; The adventuring party has an item in their possession that the villain needs. His initial attempts to infiltrate and persuade them have failed miserably. Two attempts to kill the adventuring party have been thwarted, and now he's just done with this. He intends to put one of the adventurers into a life or death situation where their only salvation is to relinquish this item that he desires. 

The issue I have is that my players are smart, they're crafty, and they're good at finding ways around, or through, problems. I'm not complaining about that, it keeps me on my toes, and I enjoy the constant need to stretch myself to accommodate them.

What I would like is to see if I could get help creating a no win situation for the players that has an emotional tug on them. For example in a show I watched recently the protagonist had to rescue a little girl, the villain allowed the little girl to be found, as the protagonist was rescuing the girl the villain trapped them both. The villain then told the protagonist to reveal information that was critical, the protagonist refused, the villain then turned on a refrigeration unit. If the protagonist didn't reveal the information he and the girl would die. If it were the protagonist it would be fine, just die, but the girl, he couldn't let an innocent die. 

I'm stumbling around with this one, I was wondering if any of you might have an idea or two?

I think you have the solution already.

Threaten the Hero(ine) and they just laugh at the Villain: "Do your worst, I will not be broken, for my heart is pure and I have the strength of 10!". They get to affirm that they're playing a Hero, and all they have to do is resist the villain to show they are heroic.

Now - if someone else, and innocent, has to suffer for their stubbornness, that's a different kettle of fish. What kind of "hero" lets innocents die? Now their resistance is at direct odds with their (self?) image of being a Hero.

So - find innocents to threaten: family, beloved NPCs, people from their back-story, etc. Make it personal to the players, and make it public.

Force them to choose between their self/public image as a hero ( and/or their public reputation ), and holding onto the item.

Of course, this doesn't work if your party is evil, or a collection of anti-hero archetypes.

Well, the party isn't evil, they've just recently been informed that they're the potential harbingers of world changing events. 

I have a general understanding of what pieces should be involved with the scenario, as you pointed out Vedexent. The innocent victim, the personal struggle and the public (or perceived public) ramifications of action or inaction.

The issue I'm having is putting those pieces together. If it helps:

I'm looking to see if anyone might have a scenario that they've done that might fit this idea, or if anyone has tried something like this and has some "Do not do" tips.

in a game I ran many years ago I had a similar problem, the villian wanted a magical compass the players had. What I did was the villian used his undead minions to attack a small town full of good people. Not a big enough threat to kill more then one or two people a night. The villian made sure the hero's found out and even used a henchman to pay them to discover why evil had struck wet stone, that was the town, named after a largenstone in the center of town that is always damp in cause you care hehe.

Anyways once the pics showed up they killed a henchman and stoped the undead! Such noble and good hero's they deserved a festival. The town people lashed love and worshipped them, they did contests and the bard sand for the town children. Then as midnight rolled around the hero's, half drunk were confronted by the villian. On the outskirts of town a horde of undead waited. The villian gave them a choice.

Give him the compass, or the town people get slaughtered.

It worked for me cause the players were all good, one was a paladin. Secondly spent a lot of time role-playing the town's people. I did cheat one player was a child care provider, so threading the town children was a touch personal.

Honesty doubt this was much help but reminded of that event so i felt the need to share. I could also see a druid of malar doing a similar thing but with wild animals.

Quote from Veth13 >>

The villian made sure the hero's found out and even used a henchman to pay them to discover why evil had struck wet stone, that was the town, named after a largenstone in the center of town that is always damp in cause you care hehe.

 

I named the major city of the continent Whitebridge...because it has a large bridge spanning a lake made of pure white mable. Sometimes the most simple names are found in landmarks!

Quote from Veth13 >>

Anyways once the pics showed up they killed a henchman and stoped the undead! Such noble and good hero's they deserved a festival. The town people lashed love and worshipped them, they did contests and the bard sand for the town children. Then as midnight rolled around the hero's, half drunk were confronted by the villian. On the outskirts of town a horde of undead waited. The villian gave them a choice.

Give him the compass, or the town people get slaughtered.

It worked for me cause the players were all good, one was a paladin. Secondly spent a lot of time role-playing the town's people. I did cheat one player was a child care provider, so threading the town children was a touch personal.

Honesty doubt this was much help but reminded of that event so i felt the need to share. I could also see a druid of malar doing a similar thing but with wild animals.

Most of my group would fall under the same psychological trap, 2 of them are child care workers, 1 is a nurse, and the 3rd is a mother of 2. However there is one player in my group who answers almost every problem with a fireball, so I'd have to find a way to remove his impulses from the equation.

I love naming towns based on key features. It give the players at least one thing to make each town different then the rest.

As far as your fireball thrower, my suggestion would be either handle it two ways. 

Either let your villian approach the most rational, or sensitive player and make the demand without Mr blow them up knowing. Alternately fireball could be passes out drunk.

Or if you don't mind the campign going dark, let him throw a fireball, the wild animals attack and the players get to try the futile attempt to save as many villagers as possible, with the villian shouting over the screams of the innocent that it can all stop if the give him what he wants. 

I've definitely considered letting his actions cause that kind of catastrophe, I've been known to throw situations at players where combat is the wrong answer.

I really would like to try to avoid giving combat as a possible solution to this situation, some how making it so that combat is either unavailable or such a blatantly bad idea that the players put that on the "no" pile almost immediately. 

I get you, when it's possible players almost always shoot first, sad but true fact, at least in d&d. 

What about something along my previous lines but then let the pcs leave the town. Maybe to the cheering of the town, and few tears, reinforcing the town loves the players, and letting the players grow to love the praise they are receiving.

Latter down the road a hour or so, the villian  or one of his minions shows up. Holding a villager hostage, maybe one a player likes. Maybe a child, to be extra dark, that the bard rembered listening wide eyed at one of the tales the bard told the previous night. The villian says give me the item or the town gets it, along with this wee little one that is proof I can destroy the whole town.

Now pcs can't fight or the hostage, and the town get it. I wouldn't use the main villian, or maybe have him and some of his minions so the pcs don't think they can burn him down and save the town that way

I had someone else give a very similar idea, so far it seems the most prevalent thought: villain proves his power by killing someone, grabs another hostage, or hostages, threatens them and the entire town with a great catastrophe and then asks for the item. 

I'm trying to come up with a way to present this to take out as many variables, meaning party members, from the equation as possible. 

Hmm...

Small town, capture someone of note in the community, show down @ high noon in the center street, sword held to the victims throat, in front of the townspeople ( lots of archers on the rooftops in case the party gets any ideas)? Have the victims small daughter run up to the party and exlaim "that's my daddy! help him!" ? Give the villain a means of getting away from the party quickly, while they're occupied, after the exchange occurs ( setting the local tavern on fine with a bunch of innocent people inside the boarded up building, forcing the party to either save the people or capture the villain ).

Capture a family member from someone with a large, tightly knit family, and announce the ransom situation to the entire family?

I note that when you describe the party you're doing so in terms of class, subclass, and level. Given that this is a psychology/personal motivation conflict you really need to dig into the characters' backstories and backgrounds. What the capabilities of the characters are is secondary; this is an attack on their character/integrity.

Ultimately, I don't think you can guarantee that the players won't try to fight their way out of the situation. That's just a side effect of player agency and free will; you can't forbid them from doing something stupid. If they do - you can't blink - the villain has to be the villain; have them execute the hostage - publicly, messily, and immediately. Villains are bad people.

In short - I think you can make a "no win situation", in the sense that you can structure it so all the outcomes are undesirable. I don't think you can make a "no win situation" in which players will free are guaranteed to pick a specific outcome. 

I am all too familiar with players doing things that are outside the scope of what I expected, the fun of ingenuity. 

We're pretty much on the same page when it comes to presenting them with a lesser of the evils decision. I also understand what you mean when it comes to the players deciding to fight, a villain must act the part.

always remember you don't try to kill spiderman you got after mary jane. attack what ever they hold most dear. what resources does your villain have? maybe have them start finding bodies of NPC's they've interacted with in the past the villain has been interrogating to get more info about the party. get their friends and dangle them over a pool of acid locked behind a prismatic wall.

So here's the plan, tentatively, based on the feedback I've been given:

Leadin:
The players are entering a major Dwarven city, Ironhaven where an event is being held that has people from all over the continent coming to attend. They've already seen Elves, Humans, and Halflings showing up by large caravans. They are escorting a caravan from the capital city of the humans, Whitebridge, to Ironhaven. This gives the opening for the villain to create mischief.

Setup:
One of the players is excited at the prospect of meeting her long lost friend and childhood crush when they reach Ironhaven. I'm going to have this friend on the fence about joining ranks with the villain's circle. He'll express a task he's been given, retrieving the missing artifact piece, and talk at length about how it's going to be used to save people. I know the players will react to this, and depending on the reaction I'll have this friend ask one of two questions: can I have the piece, or can I have your help bringing this piece where it needs to go.

Ending:
Either direction this heads the players will learn that this friend has been duped by the circle. If the friend gets the piece, they'll start to see the results of the finished artifact, cities attacked, outposts being razed, etc. If the friend joins the group, they'll be witness to the exchange and have the classic cinematic moment where they hear the monologue of the villain as they see the final piece being put into place. When the artifact is finished, there is a test of power, the friend is turned into a lycanthrope and attacks the party, allowing the villain to escape.

Again this is just a rough idea, so I'm up for adjustments.

Firstly, if the PARTY is clever, how good are they if they're parted? It might be possible to lull them into a false sense of security while they're in town so they drift apart to shop, drink or whatever and strike them one or two at a time.

Another good way around the guy who always shoots first: Have his first shot be fatal to innocents. The bad guy appears with a group of children soaked in oil. One spark and they roast alive. Most of the really destructive AoE spells involve fire or electricity...either of which can spark oil. Also, if the fight goes against him the bad guy can always activate a slow-burning spell or device that the PCs can stop but he'll escape in the process.