Despite what it says in the title, I'm hoping nobody in the party actually dies, though downing someone and forcing death saves would be nice.
Backstory to the question, the players have been causing a lot of problems to a local crime ring, and some very powerful people in the city. They've been spotted a few times (despite their best efforts to disguise themselves) one of the party members is rather identifiable, (Green Tiefling with a broken horn). So at this point, the people in charge know there is a group of roughly five people give or take, working against them, and one is likely a green tiefling with a broken horn. I've considered rumors and such that the gang is looking for the tiefling, but the party has sadly not been very 'ear to the ground' so I don't know how to "show my hand" as it were, that a hit has been put out on that member of the party.
So my problem, I suppose, is..
An Assassin is now hunting the party, how do I "spring the trap" without the party feeling cheated, or like it "Came out of Nowhere" (especially if it's a difficult encounter, because Idealy they need to realize that the people they're messing with are more dangerous than the two-bit-thugs they've been roughing up on the docks). Equally though, I don't want to run an Assassin encounter where they're rather clumsy, or tip their hand that they're hunting the party (As I fear that might go against the idea that these are rather skilled assassins).
I considered having the killer tail them for a few days, and having the party make a few perception checks here and there, but presuming they fail them all, I know from a purely argumentative stance "You had a chance to notice the Assassin and you failed" but, from a fun stance, I know as a player I'd feel cheated if I was doing my shopping in town and was randomly downed turn one, and the rest of my party had to fight tooth and nail to save me against a threat they didn't even realize existed.. but also maybe I've overthinking if they'd feel bad about it.. I can't really ask my players without giving away the game.
(Again, at the end of the day, I'm hoping nobody -actually- dies in the party, but you never know how an encounter will go. [There is a temple in town, and they can get a resurrection in exchange for giving the temple a favor which will probably be a fetch quest, but, I don't want the fact that "You can always resurrect" to be a good justification for an assassin killing a party member out of the blue.])
I’d keep it simple. The assassin and their crew set up an ambush in town one night. Assassin stealth rolls vs party passive perception, and let the dice roll what they may. And, as this is a hired, top-tier assassin, don’t be bashful about giving them stealth expertise and resources to have someone cast pass without trace on them
If you like the idea of a recurring villian, you can always give the assassin something like a cape of the mountebank so they can get away.
Also, if you want to put them on edge, you can poison them. Depending on their level, they may have the spells to turn it into a serious issue, or just kind of an annoying warning that someone is after them.
I recommend, rather than an assassin targeting one PC, which will inevitably make that player feel picked on, just use some other (probably custom) monster that hits the entire party with some sort of area effect. I don't know what level your PCs are, the last time I did something similar I had a couple of vampire spawn with class levels (ranger and wizard) sneak up on the party and ambush them with fireballs, which almost took them out, but, well, life cleric, and then they retreated when they ran out of fireballs. The players, of course, wanted those things dead, but no individual felt picked on.
If the gang as a whole is looking for this tiefling, then a bunch of people probably know about it. You can have a low-level thug spot the party and begin trailing them, hoping to curry favor with their boss. Sooner or later, the party will pass a perception check, or the thug will fail a stealth or deception check to blend in. If captured, the thug will try and save their skin by saying there's a bunch of people looking out for the party. If the thug dies before talking, on their body happens to be a piece of paper which mentions "-group of about 5" and "-green-skinned tiefling with a broken horn" and "-dangerous." If the party manages to alert the thug that their cover is blown and the thug flees before being captured or killed, have the players make an group Insight check, and whatever they roll, say that "it seems like someone was following the party for some reason," with the level of detail depending on the level of success in the roll.
With the clue planted, your conscience is clear. It's up to the party to investigate further and take notice. Spring the ambush at your convenience.
There are lots of possible breadcrumbs because if a gang has put out a hit on the players lots of people know about it, not just the assassin. You can have things like:
A bartender has secret connections to the underworld and knows about the hit, so starts acting cagey when the party come in.
Random thugs start staring at the party, or specifically the green tiefling when they are walking around town.
A guard who is investigating the gang / underworld might start tailing the party hoping the spot any assassins coming after them.
People in the shady part of town might start avoiding the party not wanting to get involved or be caught in any cross fire.
The assassin themselves might tail the party and could potentially be spotted.
Two or more assassins might take the same contract and get into a kerfuffle with each other that might be noticed by the party.
And remember any information that you think is crucial to them enjoying the story doesn't need a successful check to learn. You can just included it in your descriptions of the area / people.
I'd suggest not having it be an assassin hunting the party, for several reasons:
The concept of an assassin, where they attack out of nowhere and you have a high risk of sudden death is badly incompatible with how D&D combat works
If you do try it, it's highly unlikely to be satisfying in play
As mentioned, it could make the distinctive part member feel picked on
I'd suggest starting with an ambush, where their enemies send out some serious muscle.
If you do want to go the assassin route, I'd try poison. Make up a nasty poison with a steady deterioration effect. Say it's magic to explain why regular anti-poison magic won't help, and send them scrambling to find someone willing to risk pissing off the bad guys to provide a cure.
It is generally exceedingly difficult to assassinate anyone. It’s within the realm of possibility for the first level or two, maaaaybe three but it’s not very long before the ability to cause damage is outstripped by HP pools. This is one of the reasons that Assassin is not a terrifically popular subclass. Unless you are in the earliest levels of the game, it is unlikely you will kill the character you target. I’d say just go for it. Hit the target character with a single assassin and I suspect you’ll be surprised how easily your murder is routed. It’s kind of baked into the game that you can’t instant kill victims and for pretty good reason: it’s not much fun to have your character killed without any chance to do something about it—players are supposed to have agency.
As far as being picked on, some people will accuse you of that no matter what you do. You have put the hints out there. If there is grumbling, point out what the players have missed, the things you have been doing to indicate something is headed their way that they have not observed or paid heed. At the same time, be aware that what constitutes an obvious clue or warning to you can be hard to detect as a player. It’s very difficult to separate the wheat from the chaff in the massive amounts of information coming at a player so you really have to lay it on thick as a DM. Remind them over and over in a variety of ways the things you consider clues and warnings because dropping one ominous sentence in one NPC conversation will almost certainly be overlooked. Your players are like a group of blind people describing an elephant, able to identify only disjointed scraps of the massive animal, while you are the sighted one who knows its entirety. It’s your job to help them fill in the details not take advantage of the fact that they are blind.
1) Local merchants start to refuse service to the party. Local thugs have "advised" them that dealing witht he party isn't good for business. Maybe have a merchant with bruises/light injuries after the thugs paid them a visit. This can be revealed through roleplay and some easy charisma based checks or insight checks.
2) If the party have a regular room in a tavern of house they use as a home base have it burgled, rooms tossed etc and some minor thing stolen.
3) adding to number 2.....have their "home base" set on fire one night. Then have a timer set up for each players turn as they try to escape. The quicker they get out the easier it will be to put out the fire.You could use the fog cloud spell to represent smoke effects and create bonfire for the fire and potential damage. But, whatever happens, the fire doesn't burn the whole place down, as the party escape and raise the alarm their neighbours etc come out to help douse the flames.
4) have the "assassin" befriend the party, become an ally. The assassin uses this time to assess the party, learn their strengths and weaknesses, feed info back to the crime ring and set up accidents, put the party in the wrong place at the wrong time etc and try to make the party a patsy for the crime rings activities etc.
An assassin would attempt to hit an isolated target and flee if it fails. Ideally this occur away from the party but that's where things can go ugly, so if you want an assassination attempt on the PC without necessarily killing it, you could for example;
A) have a weaker NPC that give the lone character a tought fight which has chance to survive because the PC killed the assassin or the assassin fled, or drop it but got interrupted before it could finish the job and gamble with death saving throw.
B) Have a stronger NPC that strike out when alone but the party is close enought to intervene shortly after and join the fight, either in the toilet, bushes, seperate bedroom etc...
One way or another, i would arrange for them to find a scroll with coded target info, such as handout below, because i like this sort of prop :)
This would make a different combat encounter than typical ones 2f2 or ambush and may urge the party to look for the the people responsible for it. Perhaps the scroll used a rare ink that smell of anis which then they can track the origin back to a person or place who manufactured it and that reveal whom he last sold to.......
If every hint/thing is that slow for the party to pick up, then just be blunt.
I assume the party is high enough level that they have "contacts/friends". So on the street/alley/etc. Have then come across that person, who is extremely surprised to see them. Have him make a comment that he is so glad they are still alive and looking well, then have that NPC literally run away from them before he can answer any questions.
If that doesn't wake up the party, not sure what in game will.
These are some great ideas! Thanks all. They do have a recurring Inn they've been using, so I might have them return to turned over rooms! I kinda had in mind that some of the grunts would know there was a hit, but hadn't considered that it's leaked into more casual life, like bartenders and such, so that's a good angle as well!
You said "hit someone and put him in death saves on turn 1". That means one unlucky player isn't doing ANYthing for that first combat.
Consider: An NPC that the party likes is with them in town when the assassin strikes. That NPC goes down into death saves. All the players get to DO something in the subsequent combat.
To me it's not that dramatic that a player character miss 1+ rounds making Death Saving Throw because of an assassination attempt, on the contrary, it makes it even real scary.
One thing i just thought is to build up tension by having informations coming to them and also possibly get a first assassination attempt unexpectedly not by frontal assault but poisoning. For example, they hear at the local tavern that the local crime ring (LCR) has put a contract on the head of a party member. The bartender says ''i don't know what you did but you're in big trouble''...
Days later, they learned through checks or bribery that a shady cloaked figure was here, asking question about the party and looking for Green Tiefling with a broken horn, most likely a LCR member, affiliate or contractor. A witness says ''i don't know what you did but you're in big trouble''...
Very next visit at tavern inn, while drinking the Green Tiefling suddenly realise his drink taste weird and got poisoned very hard and must make a Constitution Saving Throw DC 25 Failure: The target has the Poisoned condition for 1 hour. While poisoned in this way, it's reduced to 0 Hit Points and has the Unconscious condition. Success: The target has the Poisoned condition for 1 hour. While poisoned in this way, it's reduced to 0 Hit Points and has the Unconscious condition but remain aware while making Death Saving Throws.
Then, multiple stores or local tavern inn they visit refuse to deal with the party as they don't want trouble with the LCR. Clerks all says ''i don't know what you did but you're in big trouble''...
Next day, a random pedestrian stop the party and tell the Green Tiefling it should go look for LCR before they find him, saying ''i don't know what you did but you're in big trouble''...
Next day, a local flower shops deliver the party flowers with a card written ''Congratulations, your recent achievements hasn't gone unoticed. If you didn't leave town tomorrow, final round of drinks is on us -LCR''
Day later if still in town, in their room is a message on a scroll saying... ''We know what you did and will kill you all for it. Let's meet tonight at twelve bells in the cemetery -LCR''
If the party go to the cemetery, nobody shows up but a rover dog. Watch them react on it this should create tension and stress them up! : )
Next move from the party or LCR to be determined......
To me it's not that dramatic that a player character miss 1+ rounds making Death Saving Throw because of an assassination attempt, on the contrary, it makes it even real scary.
100% it depends on the group. I've had at least one table that if I said 'Bill, your character gets hit by the assasin's arrow, dropping you to 0 HP, make your first death save. Oh, and everyone roll intiative', I'd be in trouble. And part of that would be after the combat if Bill never got to do any thing because they were 'down' the entire fight, or at least most of it. It's about the table and the dynamic. :D
I've also had tables (my current Thursday group) that would 100% roll with it and have a blast.
Yeah it depends of group for sure and on an attack that suddenly hit outside combat Initiative order to me may feel more arbitrary than some other effects occuring after a Saving Throw.
But the consequence of being at 0 making Death Saving Throws for at least a turn isn't that big of a deal in itself, it happen often in combat, and usually heal quickly comes their way. At my table the trouble would be if no one heals the Unconcious character, especially before it gets 3 failure.
But this occuring during an assassination attemps by some spell or poison effect for example is what makes thing different than normal combat and bound to have the party say Wow oh boy what's going on...
And like the DM said doesn't want to kill a PC but come close to, so such failed assassination should at least has Wow Factor of some sort as for me it's a great opportunity to create an encounter that feels different than most others in the purpose behind it, its execution and reaction caused.
There is a bounty on the groups Head, so your local Tavern Keeper wants it.
He tries to poison the group, strong alcohol or sleeping pills. Then he tries to kidnap and deliver them.
Between drinking, sleeping, being tied up and being transported to the thief’s guild (or whatever) there are plenty opportunities to break free and question an NPC what’s going on. (Worst case one of the dead bad guys can carry a letter mentioning the bounty)
Despite what it says in the title, I'm hoping nobody in the party actually dies, though downing someone and forcing death saves would be nice.
Backstory to the question, the players have been causing a lot of problems to a local crime ring, and some very powerful people in the city. They've been spotted a few times (despite their best efforts to disguise themselves) one of the party members is rather identifiable, (Green Tiefling with a broken horn). So at this point, the people in charge know there is a group of roughly five people give or take, working against them, and one is likely a green tiefling with a broken horn. I've considered rumors and such that the gang is looking for the tiefling, but the party has sadly not been very 'ear to the ground' so I don't know how to "show my hand" as it were, that a hit has been put out on that member of the party.
So my problem, I suppose, is..
An Assassin is now hunting the party, how do I "spring the trap" without the party feeling cheated, or like it "Came out of Nowhere" (especially if it's a difficult encounter, because Idealy they need to realize that the people they're messing with are more dangerous than the two-bit-thugs they've been roughing up on the docks). Equally though, I don't want to run an Assassin encounter where they're rather clumsy, or tip their hand that they're hunting the party (As I fear that might go against the idea that these are rather skilled assassins).
I considered having the killer tail them for a few days, and having the party make a few perception checks here and there, but presuming they fail them all, I know from a purely argumentative stance "You had a chance to notice the Assassin and you failed" but, from a fun stance, I know as a player I'd feel cheated if I was doing my shopping in town and was randomly downed turn one, and the rest of my party had to fight tooth and nail to save me against a threat they didn't even realize existed.. but also maybe I've overthinking if they'd feel bad about it.. I can't really ask my players without giving away the game.
(Again, at the end of the day, I'm hoping nobody -actually- dies in the party, but you never know how an encounter will go. [There is a temple in town, and they can get a resurrection in exchange for giving the temple a favor which will probably be a fetch quest, but, I don't want the fact that "You can always resurrect" to be a good justification for an assassin killing a party member out of the blue.])
Ask each character/player independently of the others about how would they feel if a party member was a target of an assassination by a guild they inadvertently disrupted. If needed you could have an “flashback insight check” mini game that lets the group discover their predicament, and if they are lucky discover the target of the hit.
That way, the group gets a hint something isn’t right, but if they can’t put it together, then when the “hit” happens, well Surprise!
( just be sure if you really want to go down the Marked for Early Life Retirement path, the intended target knows what might happen[ and has to Out Of Character and In Character keep that meta 4th wall info as something that ‘might’ happen.]. Have the target toss a d100 and set a trigger value that sets the assassination attempt into action, and explain later is a second option.)
[ Hint: blindsiding an unsuspecting character/player is never a good look, you just have to trust the player can keep quiet about the possibility it might happen, or have the character realize they messed up and are now possible prey. ]
Make it so that one party member (like a ranger or rogue, since they are usually super sensitive to things that are off) sees the assassin everywhere, but every time they try to show the party, they aren't there. Then one day a person comes up to them and says they are being stalked and tells them to follow them, answering questions super vaguely to get them to follow them ("I told you to follow me, we can't talk here. This city has eyes" or something like that) then if they follow the person they lock the door behind them and a group of people approach from the shadows saying something like "We dont like those who hurt our family" or something.
You could have the assassin try poison first which might alert the party that something is up. The poison could be deadly for some species but perhaps the green Tiefling has some natural resistance or is lucky and doesn't quite get the full dose (or maybe they are unlucky, fall unconscious and start making death saves unless the party burns through healing potions to keep them alive long enough to get to a healer who could cast cure poison.
I also didn't notice whether you mentioned the party level, party composition and whether there are healing/resurrection services available. All of this could affect how deadly you want to make he encounter.
You could also have the crime lords want these people captured alive so that they could be made an example to keep the rest of the town in line. This way, whether they win or not, the adventure continues and you don't care which way it turns out.
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Despite what it says in the title, I'm hoping nobody in the party actually dies, though downing someone and forcing death saves would be nice.
Backstory to the question, the players have been causing a lot of problems to a local crime ring, and some very powerful people in the city. They've been spotted a few times (despite their best efforts to disguise themselves) one of the party members is rather identifiable, (Green Tiefling with a broken horn). So at this point, the people in charge know there is a group of roughly five people give or take, working against them, and one is likely a green tiefling with a broken horn. I've considered rumors and such that the gang is looking for the tiefling, but the party has sadly not been very 'ear to the ground' so I don't know how to "show my hand" as it were, that a hit has been put out on that member of the party.
So my problem, I suppose, is..
An Assassin is now hunting the party, how do I "spring the trap" without the party feeling cheated, or like it "Came out of Nowhere" (especially if it's a difficult encounter, because Idealy they need to realize that the people they're messing with are more dangerous than the two-bit-thugs they've been roughing up on the docks). Equally though, I don't want to run an Assassin encounter where they're rather clumsy, or tip their hand that they're hunting the party (As I fear that might go against the idea that these are rather skilled assassins).
I considered having the killer tail them for a few days, and having the party make a few perception checks here and there, but presuming they fail them all, I know from a purely argumentative stance "You had a chance to notice the Assassin and you failed" but, from a fun stance, I know as a player I'd feel cheated if I was doing my shopping in town and was randomly downed turn one, and the rest of my party had to fight tooth and nail to save me against a threat they didn't even realize existed.. but also maybe I've overthinking if they'd feel bad about it.. I can't really ask my players without giving away the game.
(Again, at the end of the day, I'm hoping nobody -actually- dies in the party, but you never know how an encounter will go. [There is a temple in town, and they can get a resurrection in exchange for giving the temple a favor which will probably be a fetch quest, but, I don't want the fact that "You can always resurrect" to be a good justification for an assassin killing a party member out of the blue.])
I’d keep it simple. The assassin and their crew set up an ambush in town one night. Assassin stealth rolls vs party passive perception, and let the dice roll what they may. And, as this is a hired, top-tier assassin, don’t be bashful about giving them stealth expertise and resources to have someone cast pass without trace on them
If you like the idea of a recurring villian, you can always give the assassin something like a cape of the mountebank so they can get away.
Also, if you want to put them on edge, you can poison them. Depending on their level, they may have the spells to turn it into a serious issue, or just kind of an annoying warning that someone is after them.
I recommend, rather than an assassin targeting one PC, which will inevitably make that player feel picked on, just use some other (probably custom) monster that hits the entire party with some sort of area effect. I don't know what level your PCs are, the last time I did something similar I had a couple of vampire spawn with class levels (ranger and wizard) sneak up on the party and ambush them with fireballs, which almost took them out, but, well, life cleric, and then they retreated when they ran out of fireballs. The players, of course, wanted those things dead, but no individual felt picked on.
If the gang as a whole is looking for this tiefling, then a bunch of people probably know about it. You can have a low-level thug spot the party and begin trailing them, hoping to curry favor with their boss. Sooner or later, the party will pass a perception check, or the thug will fail a stealth or deception check to blend in. If captured, the thug will try and save their skin by saying there's a bunch of people looking out for the party. If the thug dies before talking, on their body happens to be a piece of paper which mentions "-group of about 5" and "-green-skinned tiefling with a broken horn" and "-dangerous." If the party manages to alert the thug that their cover is blown and the thug flees before being captured or killed, have the players make an group Insight check, and whatever they roll, say that "it seems like someone was following the party for some reason," with the level of detail depending on the level of success in the roll.
With the clue planted, your conscience is clear. It's up to the party to investigate further and take notice. Spring the ambush at your convenience.
There are lots of possible breadcrumbs because if a gang has put out a hit on the players lots of people know about it, not just the assassin. You can have things like:
And remember any information that you think is crucial to them enjoying the story doesn't need a successful check to learn. You can just included it in your descriptions of the area / people.
I'd suggest not having it be an assassin hunting the party, for several reasons:
I'd suggest starting with an ambush, where their enemies send out some serious muscle.
If you do want to go the assassin route, I'd try poison. Make up a nasty poison with a steady deterioration effect. Say it's magic to explain why regular anti-poison magic won't help, and send them scrambling to find someone willing to risk pissing off the bad guys to provide a cure.
It is generally exceedingly difficult to assassinate anyone. It’s within the realm of possibility for the first level or two, maaaaybe three but it’s not very long before the ability to cause damage is outstripped by HP pools. This is one of the reasons that Assassin is not a terrifically popular subclass. Unless you are in the earliest levels of the game, it is unlikely you will kill the character you target. I’d say just go for it. Hit the target character with a single assassin and I suspect you’ll be surprised how easily your murder is routed. It’s kind of baked into the game that you can’t instant kill victims and for pretty good reason: it’s not much fun to have your character killed without any chance to do something about it—players are supposed to have agency.
As far as being picked on, some people will accuse you of that no matter what you do. You have put the hints out there. If there is grumbling, point out what the players have missed, the things you have been doing to indicate something is headed their way that they have not observed or paid heed. At the same time, be aware that what constitutes an obvious clue or warning to you can be hard to detect as a player. It’s very difficult to separate the wheat from the chaff in the massive amounts of information coming at a player so you really have to lay it on thick as a DM. Remind them over and over in a variety of ways the things you consider clues and warnings because dropping one ominous sentence in one NPC conversation will almost certainly be overlooked. Your players are like a group of blind people describing an elephant, able to identify only disjointed scraps of the massive animal, while you are the sighted one who knows its entirety. It’s your job to help them fill in the details not take advantage of the fact that they are blind.
Further to the ideas above:
1) Local merchants start to refuse service to the party. Local thugs have "advised" them that dealing witht he party isn't good for business. Maybe have a merchant with bruises/light injuries after the thugs paid them a visit. This can be revealed through roleplay and some easy charisma based checks or insight checks.
2) If the party have a regular room in a tavern of house they use as a home base have it burgled, rooms tossed etc and some minor thing stolen.
3) adding to number 2.....have their "home base" set on fire one night. Then have a timer set up for each players turn as they try to escape. The quicker they get out the easier it will be to put out the fire.You could use the fog cloud spell to represent smoke effects and create bonfire for the fire and potential damage. But, whatever happens, the fire doesn't burn the whole place down, as the party escape and raise the alarm their neighbours etc come out to help douse the flames.
4) have the "assassin" befriend the party, become an ally. The assassin uses this time to assess the party, learn their strengths and weaknesses, feed info back to the crime ring and set up accidents, put the party in the wrong place at the wrong time etc and try to make the party a patsy for the crime rings activities etc.
An assassin would attempt to hit an isolated target and flee if it fails. Ideally this occur away from the party but that's where things can go ugly, so if you want an assassination attempt on the PC without necessarily killing it, you could for example;
A) have a weaker NPC that give the lone character a tought fight which has chance to survive because the PC killed the assassin or the assassin fled, or drop it but got interrupted before it could finish the job and gamble with death saving throw.
B) Have a stronger NPC that strike out when alone but the party is close enought to intervene shortly after and join the fight, either in the toilet, bushes, seperate bedroom etc...
One way or another, i would arrange for them to find a scroll with coded target info, such as handout below, because i like this sort of prop :)
This would make a different combat encounter than typical ones 2f2 or ambush and may urge the party to look for the the people responsible for it. Perhaps the scroll used a rare ink that smell of anis which then they can track the origin back to a person or place who manufactured it and that reveal whom he last sold to.......
If every hint/thing is that slow for the party to pick up, then just be blunt.
I assume the party is high enough level that they have "contacts/friends". So on the street/alley/etc. Have then come across that person, who is extremely surprised to see them. Have him make a comment that he is so glad they are still alive and looking well, then have that NPC literally run away from them before he can answer any questions.
If that doesn't wake up the party, not sure what in game will.
These are some great ideas! Thanks all. They do have a recurring Inn they've been using, so I might have them return to turned over rooms! I kinda had in mind that some of the grunts would know there was a hit, but hadn't considered that it's leaked into more casual life, like bartenders and such, so that's a good angle as well!
Something to muse on:
You said "hit someone and put him in death saves on turn 1". That means one unlucky player isn't doing ANYthing for that first combat.
Consider: An NPC that the party likes is with them in town when the assassin strikes. That NPC goes down into death saves. All the players get to DO something in the subsequent combat.
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To me it's not that dramatic that a player character miss 1+ rounds making Death Saving Throw because of an assassination attempt, on the contrary, it makes it even real scary.
One thing i just thought is to build up tension by having informations coming to them and also possibly get a first assassination attempt unexpectedly not by frontal assault but poisoning. For example, they hear at the local tavern that the local crime ring (LCR) has put a contract on the head of a party member. The bartender says ''i don't know what you did but you're in big trouble''...
Days later, they learned through checks or bribery that a shady cloaked figure was here, asking question about the party and looking for Green Tiefling with a broken horn, most likely a LCR member, affiliate or contractor. A witness says ''i don't know what you did but you're in big trouble''...
Very next visit at tavern inn, while drinking the Green Tiefling suddenly realise his drink taste weird and got poisoned very hard and must make a Constitution Saving Throw DC 25 Failure: The target has the Poisoned condition for 1 hour. While poisoned in this way, it's reduced to 0 Hit Points and has the Unconscious condition. Success: The target has the Poisoned condition for 1 hour. While poisoned in this way, it's reduced to 0 Hit Points and has the Unconscious condition but remain aware while making Death Saving Throws.
Then, multiple stores or local tavern inn they visit refuse to deal with the party as they don't want trouble with the LCR. Clerks all says ''i don't know what you did but you're in big trouble''...
Next day, a random pedestrian stop the party and tell the Green Tiefling it should go look for LCR before they find him, saying ''i don't know what you did but you're in big trouble''...
Next day, a local flower shops deliver the party flowers with a card written ''Congratulations, your recent achievements hasn't gone unoticed. If you didn't leave town tomorrow, final round of drinks is on us -LCR''
Day later if still in town, in their room is a message on a scroll saying... ''We know what you did and will kill you all for it. Let's meet tonight at twelve bells in the cemetery -LCR''
If the party go to the cemetery, nobody shows up but a rover dog. Watch them react on it this should create tension and stress them up! : )
Next move from the party or LCR to be determined......
100% it depends on the group. I've had at least one table that if I said 'Bill, your character gets hit by the assasin's arrow, dropping you to 0 HP, make your first death save. Oh, and everyone roll intiative', I'd be in trouble. And part of that would be after the combat if Bill never got to do any thing because they were 'down' the entire fight, or at least most of it. It's about the table and the dynamic. :D
I've also had tables (my current Thursday group) that would 100% roll with it and have a blast.
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Yeah it depends of group for sure and on an attack that suddenly hit outside combat Initiative order to me may feel more arbitrary than some other effects occuring after a Saving Throw.
But the consequence of being at 0 making Death Saving Throws for at least a turn isn't that big of a deal in itself, it happen often in combat, and usually heal quickly comes their way. At my table the trouble would be if no one heals the Unconcious character, especially before it gets 3 failure.
But this occuring during an assassination attemps by some spell or poison effect for example is what makes thing different than normal combat and bound to have the party say Wow oh boy what's going on...
And like the DM said doesn't want to kill a PC but come close to, so such failed assassination should at least has Wow Factor of some sort as for me it's a great opportunity to create an encounter that feels different than most others in the purpose behind it, its execution and reaction caused.
There is a bounty on the groups Head, so your local Tavern Keeper wants it.
He tries to poison the group, strong alcohol or sleeping pills. Then he tries to kidnap and deliver them.
Between drinking, sleeping, being tied up and being transported to the thief’s guild (or whatever) there are plenty opportunities to break free and question an NPC what’s going on. (Worst case one of the dead bad guys can carry a letter mentioning the bounty)
Attack: [roll]3d20dl2+6[/roll] Damage: [roll](if([roll:-1:critical], =0, 1d8, 2{1d8}.expand()))+4[/roll] Sneakattack: [roll](if([roll:-2:critical], =0, 2d6, 2{2d6}.expand()))[/roll]Ask each character/player independently of the others about how would they feel if a party member was a target of an assassination by a guild they inadvertently disrupted. If needed you could have an “flashback insight check” mini game that lets the group discover their predicament, and if they are lucky discover the target of the hit.
That way, the group gets a hint something isn’t right, but if they can’t put it together, then when the “hit” happens, well Surprise!
( just be sure if you really want to go down the Marked for Early Life Retirement path, the intended target knows what might happen[ and has to Out Of Character and In Character keep that meta 4th wall info as something that ‘might’ happen.]. Have the target toss a d100 and set a trigger value that sets the assassination attempt into action, and explain later is a second option.)
[ Hint: blindsiding an unsuspecting character/player is never a good look, you just have to trust the player can keep quiet about the possibility it might happen, or have the character realize they messed up and are now possible prey. ]
Make it so that one party member (like a ranger or rogue, since they are usually super sensitive to things that are off) sees the assassin everywhere, but every time they try to show the party, they aren't there. Then one day a person comes up to them and says they are being stalked and tells them to follow them, answering questions super vaguely to get them to follow them ("I told you to follow me, we can't talk here. This city has eyes" or something like that) then if they follow the person they lock the door behind them and a group of people approach from the shadows saying something like "We dont like those who hurt our family" or something.
You could have the assassin try poison first which might alert the party that something is up. The poison could be deadly for some species but perhaps the green Tiefling has some natural resistance or is lucky and doesn't quite get the full dose (or maybe they are unlucky, fall unconscious and start making death saves unless the party burns through healing potions to keep them alive long enough to get to a healer who could cast cure poison.
I also didn't notice whether you mentioned the party level, party composition and whether there are healing/resurrection services available. All of this could affect how deadly you want to make he encounter.
You could also have the crime lords want these people captured alive so that they could be made an example to keep the rest of the town in line. This way, whether they win or not, the adventure continues and you don't care which way it turns out.