D&D 5E Fun with Assasins

[FrogReaver]

One possibility is to have the PCs hear about the assassin, perhaps because he/she/it takes out someone unrelated to them - a minor princeling, a high priest, a rich merchant. Or maybe the assassin is so infamous, every unsolved murder is inevitably blamed on him. "Hmm. This was a professional kill. Look's like (fill in the blank's) work."

Or perhaps the PCs are hired to investigate a murder by that assassin.

Another option, one of their contacts warns them that someone has put a contract out of them. If the PCs have any sense at all, they'll start to ask around about the type of folks who would take such a contract.

I like this. PC's are hired to investigate the murder of a prominent figure. As they get closer to figuring out who put the hit on that person that's when a message appears to them to cease what they are doing or else. When they continue the assassin waits patiently for a good opportunity and strikes.

Personally I'd have it be a decently leveled wizard that hired the assassin. Maybe they are good friends and work together a lot now. Either way the wizards magic + the assassins abilities would make for a fun and interesting campaign and gives lots of options leading up toward the defeat of those foes and their plot.

Maybe the would be assassin is a student of the better one that is the wizards friend. There's lots of fun twists and turns that this kind of adventure could have.

 

[5ekyu]

Agree with DocMoriarty. Assassin listens to tales of heroes, finds patterns, finds good way to,let them follow pattern into very unexpected situation, possibly using them to eliminate a rival of his own. No way going to "take on" a party when so many ruthless thugs around to be used. Then again, one of my best bad guys saw the pcs beginning to roll up his local network and so before they got wind of who he was he offered them cash to escort convoy including kids to dangerous territory to a new settlement a long ways away. Then paid them to help keep things safe there, eliminate threats and basically be a problem for someone else while his network grew. The eventual conflict was quite conflicted as they had indeed carved out a very strong safe place -which his network had infested too and that's when it all came to a head.

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[5ekyu]

Word of caution - if you game uses frequently the quick start "stranger at an inn" the above is likely not as good an idea. That quick start needs an implied level of trust between player and dm. If your game is ongoing with less quick start suspension of disbelief, it can be great tool.

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[AGrzes]

The party is now three 8 level characters, and they are quite capable - in straight fight I expect them to steamroll single DMG assassin without problems. They are also properly paranoid so I imagine that they have fair chance to spot the danger in advance.

The party have fairly good contacts so they can get accurate intelligence without this being heavy-handed but I would like to give characters the chance to spot the danger by themselves to give players the satisfaction.

I like the idea of hiring "sub-contractors" they do not even have to be trained killers - only simple thugs to test the party defenses and to wear them down.

Similarly I was thinking that their enemy can put open bounty on party instead of hiring specific professional. This would result in stream of more-or-less competent wanna-be assassins who the party can fight off but still have to deal with the source if they want to ever let their guard down.

 

[Stalker0]

Best advice is to wait for the party to get into combat with someone else, than pounce. I did that with an assassin during my high level adventure, and it was like the character in my entire campaign that made it out alive

Or you could set up a mirror of opposition ahead in a dungeon and then while they fight themselves, assassinate!