During one early game, I played a Half Elf Assassin name Kiera. She had gained a reputation as a pure professional. She always got her target it didn’t matter how long it took, and she never broke a contract.
The other PCs weren’t aware of her assassinations as she held herself as a mere fighter who was a bit quicker on her feet then most, with a penchant for Knife work, All except one Mage who finally figured it out as the two had become friends, and she (the mage, was pretty smart, an 18 int).
During its adventures the group had gotten into trouble with a local Baron. A major political player, and the Big Bad of this part of the campaign who had it in for all the group members for one reason or another. After foiling various assassination attempts, traps, and ambushes over the course of several adventures. Kiera received word from a Guild contact that the Baron was looking to hire the best assassin the guild had IE HER, and the targets would be her friends, Kiera being who she was would be honor bound to kill them all, which she would do so ruthlessly.
The Mage through, clever thing that she was, had a brilliant and absolutely terrifying idea. She made arrangements to meet the assassins guild head and on the spot Hired Kiera herself, the target? of course the Baron. But not in a straight up assassination either, the Baron was too well connected and guarded against assassins, so she came up with a ruse, the Baron would hire Kiera to kill the players. She would then do so one at a time till they were all gone and when the time came to present the players corpses as proof the job was done the trap would be sprung,
Now be aware the PCs were NOT aware of this only me and the Mages player. So the Barons request came down and Kiera took the job. She then rapidly proceeded to “”Assassinate”” each PC one at a time in various ways. The Fighter and the Cleric poisoned wine, the Ranger trapped and stabbed in the back, and lastly the mage another stab with a poisoned dagger. Kiera then presented the corpses to the Baron as proof. The Baron was of course happy but his happiness turned to shock when Kiera said a single word.
The full party woke up and stood up alive and well. the Mage when asked how said a simple phrase, “We got there first.:” then Kiera proceeded to Decapitate the Baron with a critical backstab fulfilling her original contract at the agreed upon target phrase.
the PCs assassinations had all been elaborate ruses using a special researched spell from the Mage, that put the pc in a death like state of suspended animation. The ‘poison’ used each time was part of the spell. Kiera had the command word used to release each victim from their healing sleep, so they woke up refreshed and ready for a fight.
With the Barons death chaos ensued and a running battle was fought out of the castle which went up in flames.
That’s how my assassin with the help of a sneaky mage killed a target and fulfilled a contract with out killing her friends all while raising her reputation accordingly. the PCs were understandably wary around their wine for a while afterwards