Ideas for Illithid/Ullitharid NPC as mentor in 5e

[Dohvak]

Background for you: This is a 5e homebrew lifted from the original boxed set Spelljammer, the limited information from 5e with references to it, and deriving from concepts in splat books like Sword Coast. Illithid culture in Spelljammer is being run as "Royal Illithid Trade Company" (think East India Company with black-clad Imperial uniforms).

PCs started as dirt-side and are working with another group (think Harpers in space) and trying to earn themselves a ship and training to get off the planet. They finally located a crashed jammer with a damaged helm (partially disassembled so just non-functioning). The jammer is still in possession by its old captain, an Ulitharid pirate that has been on the lamb for nearly 100 years and they finally tracked to having crashed into this planet some 50 years ago. The item he stole also has alienated him from the illithid communities.

Hired as bounty hunters and given the authority to barter up to and including a pardon, the PCs had the power to win the fight, snuck in, and from a position of power they asked for parley. The negotiator finished negotiations with official pardon that they were empowered to offer and then continued to offer an alliance with the now x-pirate.

A binding Geas to all present as a vow of non-violence to those present, and they would apprentice to the Ulitharid and do favors for him in return for this mentorship.

The Ulitharid is nearing 800 years old, a high level Sorcerer of Sea (no longer requires food, water, air, etc.), and has built himself a fairly secreted island lair with a huge tribe of thralled bugbears and has hidden spawning pools nearly completed so leaving the area is not something he wishes to do. Having the PCs as allies, getting pardoned so long as he doesn't partake in piracy anymore, and becoming patriarch to his own clan all appeal to him.

As mid-level adventurers, what kinds of mentoring could work? This is so non-standard I am kind of at a loss as to the benefits of what this relationship could be. The captain knows that asking the PCs to do anything against their nature might lose him the alliance, but space-faring adventurers would be a huge boon to him and his plans.

[Lvl45DM!]

Background for you: This is a 5e homebrew lifted from the original boxed set Spelljammer, the limited information from 5e with references to it, and deriving from concepts in splat books like Sword Coast. Illithid culture in Spelljammer is being run as "Royal Illithid Trade Company" (think East India Company with black-clad Imperial uniforms).

PCs started as dirt-side and are working with another group (think Harpers in space) and trying to earn themselves a ship and training to get off the planet. They finally located a crashed jammer with a damaged helm (partially disassembled so just non-functioning). The jammer is still in possession by its old captain, an Ulitharid pirate that has been on the lamb for nearly 100 years and they finally tracked to having crashed into this planet some 50 years ago. The item he stole also has alienated him from the illithid communities.

Hired as bounty hunters and given the authority to barter up to and including a pardon, the PCs had the power to win the fight, snuck in, and from a position of power they asked for parley. The negotiator finished negotiations with official pardon that they were empowered to offer and then continued to offer an alliance with the now x-pirate.

A binding Geas to all present as a vow of non-violence to those present, and they would apprentice to the Ulitharid and do favors for him in return for this mentorship.

The Ulitharid is nearing 800 years old, a high level Sorcerer of Sea (no longer requires food, water, air, etc.), and has built himself a fairly secreted island lair with a huge tribe of thralled bugbears and has hidden spawning pools nearly completed so leaving the area is not something he wishes to do. Having the PCs as allies, getting pardoned so long as he doesn't partake in piracy anymore, and becoming patriarch to his own clan all appeal to him.

As mid-level adventurers, what kinds of mentoring could work? This is so non-standard I am kind of at a loss as to the benefits of what this relationship could be. The captain knows that asking the PCs to do anything against their nature might lose him the alliance, but space-faring adventurers would be a huge boon to him and his plans.

Depends on exactly what you want from this mentor.
Is it an excuse to give your characters quests? Then have him telepathically communicate with them, guide them to their quest, and have the planar turbulence cut him off whenever you don't want the players to get his advice. Hand the players sheets of information explaining the infodump as a result of him just shlooping it into their brains.
Is he teaching your characters new skills, training them? He throws them into mindscapes with training scenarios
Is he leading to an inevitable betrayal? Slow burn have them get used to accepting his orders and help and then he uses his mind powers to deceive them into committing a grave crime, and blackmails them into working for him further, or dumps the blame on them and runs.

He could give them secret illithid knowledge of spells and items and fighting styles from far in the future. He could use them to weaken outposts so he can zoom in and eat the brains afterwards. And he will be manipulating them into attacking his old hivemind and then coming in to save the hive mind from them.

[Dohvak]

Depends on exactly what you want from this mentor.
Is it an excuse to give your characters quests? Then have him telepathically communicate with them, guide them to their quest, and have the planar turbulence cut him off whenever you don't want the players to get his advice. Hand the players sheets of information explaining the infodump as a result of him just shlooping it into their brains.
Is he teaching your characters new skills, training them? He throws them into mindscapes with training scenarios
Is he leading to an inevitable betrayal? Slow burn have them get used to accepting his orders and help and then he uses his mind powers to deceive them into committing a grave crime, and blackmails them into working for him further, or dumps the blame on them and runs.

He could give them secret illithid knowledge of spells and items and fighting styles from far in the future. He could use them to weaken outposts so he can zoom in and eat the brains afterwards. And he will be manipulating them into attacking his old hivemind and then coming in to save the hive mind from them.

Had to think about your response for a while. Thank you.

Honestly I didn't expect the players (generally good aligned group) to create a situation to make an ally with a mind flayer who is a known murderer and pirate. They set the scene up ad-hoc and it came together nearly flawless and since it was unplanned by them as well I was completely caught out.

I started the mentorship with the illithid granting them access to a spell (new spell, Level 1, Attune Helm, Dispel as action, allows attuning to the helm for 8 hours speed based on level of spell slot used. Caster may attune for the 8 hours even if already attuned to 3 magic items). The spell can be learned and added to any and all spell lists.

I am imagining the illithid renegade as needing more allies to extend his reach for the moment. He will grant the PCs an orb that can cast sending once per day, only to the illithid who has a matching orb. (I love the frustration of 25 word communications/day). I kind of feel like basing the illithid as like with Star Trek when they allied with the Borg. For now, there is only one "Borg" and he will give exactly as much help to the PCs as needed to get them to do his tasks and forward his goals until he can become a new Elder Brain for the colony he is creating. As an alien intellect from another reality, his ways of thinking should be odd.

I am also considering having another ancient squid-faced intellect as the illithids ally in the back. I think Aboleth might consider an alliance with an Elder Brain worthwhile. The needs of two partners such as this extending their reach through the PCs would be a lot of fun and their schemes wouldn't make any sense to "lesser beings".

[Lvl45DM!]

Had to think about your response for a while. Thank you.

Honestly I didn't expect the players (generally good aligned group) to create a situation to make an ally with a mind flayer who is a known murderer and pirate. They set the scene up ad-hoc and it came together nearly flawless and since it was unplanned by them as well I was completely caught out.

I started the mentorship with the illithid granting them access to a spell (new spell, Level 1, Attune Helm, Dispel as action, allows attuning to the helm for 8 hours speed based on level of spell slot used. Caster may attune for the 8 hours even if already attuned to 3 magic items). The spell can be learned and added to any and all spell lists.

I am imagining the illithid renegade as needing more allies to extend his reach for the moment. He will grant the PCs an orb that can cast sending once per day, only to the illithid who has a matching orb. (I love the frustration of 25 word communications/day). I kind of feel like basing the illithid as like with Star Trek when they allied with the Borg. For now, there is only one "Borg" and he will give exactly as much help to the PCs as needed to get them to do his tasks and forward his goals until he can become a new Elder Brain for the colony he is creating. As an alien intellect from another reality, his ways of thinking should be odd.

I am also considering having another ancient squid-faced intellect as the illithids ally in the back. I think Aboleth might consider an alliance with an Elder Brain worthwhile. The needs of two partners such as this extending their reach through the PCs would be a lot of fun and their schemes wouldn't make any sense to "lesser beings".

Well don't make them too canny and unbeatable. Sounds like a good party will want to eventually turn on their treacherous manipulative mentor.

[Dohvak]

Well don't make them too canny and unbeatable. Sounds like a good party will want to eventually turn on their treacherous manipulative mentor.

This group usually leans towards holding someone's feet to the fire on maintaining their agreements, I honestly doubt they will turn on it unless the illithid fairly directly starts a deadly conflict first. I won't put a huge write-up into the thing unless they let it live. Then I will probably write a mini splat-book on the Ulitharid and its new enclave to share with the other DMs (gotta love multi-DM libraries shared in OneNote)

I plan on running the game to 14-15th level, jumping to a 17th level end-game adventure then a 20th level final adventure epilogue. Our DMing group tends to follow this model to let everyone play a little high/epic endgame without going crazy or getting headaches. We then recycle our favored story elements and reveals into the next game as backstory for whomever runs the next game... keeps the really fun bad guys as great world NPCs like old Thieves World books.