Should a GM let high level characters die?
I certainly would let them die, if that's the natural outcome of play. But old school D&D rules tend to make high level PCs robust, and also tend to make the players of high level PCs highly skilled! So it's not a common event. And it tends to be a dramatic, epochal event when it happens.
I think it was in 2016 I last saw a really high level PC perma-death: At the climax of my BECMI campaign, my son's PC the Duke-Sultan William of Castellan/Karameikos/Alasiya, an MU 18 (boosted to 19th caster via Ioun stone) was pressing home the attack against the Heldannic Knights during the Soderfjord invasion of Ostland. He had just nailed the Heldannic Knights-Marine with a well-placed fireball as their Warbird's bay doors opened, saving his party from being overrun by a couple dozen high level Fighters, when he was Disintegrated by the Heldannic Warbird's Bile Belcher cannon. AIR he was targetted 3 in 6 and would have survived on a roll of 4+ on d20, but made me roll and I got a 2. William was gone, after years of play (he had started at 4th around 4 years previously, when my son was only 5 years old!) but his side was victorious, King Hord Darkeye of Ostland was defeated, his kingdom conquered, and William was mourned by an assembly of high level heroes, including his son Bravery the new Duke-Sultan, the High Priestess Lady Roseanna and Baroness Alexandra Vorloi, all great champions in their own right.
In that case I was already planning to end the campaign with that session, although I did end up doing some epilogue stuff.
No very high level (15+) PCs have perma-died in my 5e Wilderlands sandbox game yet; High Priest Thuruar (Clr-15) did perish to the hellfire ball of the Death Knight Varek Tigerclaw*, but Hakeem the Barbarian defeated Varek and was able to get Thuruar raised by Lady Meda of Thusia. If a really major PC like Hakeem (now Barbarian-20) did die it would certainly alter the campaign (Hakeem's newly founded empire would almost certainly collapse, for a start) - but it certainly wouldn't end the campaign.
*A former PC reanimated by the Necromancer Borritt Crowfinger, BBEG of the campaign for many years until his final demise a few months ago.
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The open campaign is bigger than any one quest, but I've seen major (like 20+ session) quests emerge from play, like the time a group of PCs decided to quest far to the north of the normal campaign area to find and destroy the Gate Castle of the Black Sun. We still had a fair bit of PCs swapping in and out over those 20+ sessions, but I'd say there were 3 core PCs, and if all had died then that particular quest might logically have been abandoned/failed.
Some tears, but he took it manfully, especially for a nine year old. Since his PC was almost an Archmage I accepted his request for a 'force ghost' scene where Sultan William appeared to his widow & mother of his 4 children, Princess-Sultana Adriana the daughter of King Stefan Karameikos, back in Karameikos where it had all begun 25 game years & 4 real years before. He bid her a very touching farewell & departed to the higher worlds.
Normally players & PCs are happy to team up for adventure, whoever's idea it is, as there are rewards in fun, gold, XP etc. But I do see stuff vetoed, eg the PC Hakeem refused Shieldbiter's request to help him go up against the ancient red dragons beneath Fortress Badabaskor, rumoured to possess the sacred Dragon Armour and Dragon Shield of ancient Arkhosia.
Edit: Rely on coincidence - yes just like in the comics (Savage Sword of Conan, notably) and pulps, heroes are always running into each other in unlikely circumstances. But I also have a home base, Selatine port village, that serves as the heart of the campaign, the starting point for (most) new PCs & PC groups, etc. With lots of PCs based there they naturally interact and form adventurer parties.
Oh, also re the tabletop element, I would be willing to run up to two separate groups on alternate weeks if necessary, if the PCs split up. And I have a co-GM who helps out, running the Bratanis region, a low level campaign area west of Selatine. PCs can go back and forth from there, being GM'd by him one week then me the next.
Mileage... I *love* it when some mook NPC gets lucky and takes down a high level PC or BBEG! Not something I see often in 5e, but the Blight Belcher disintegrator cannon that took out legendary wizard Duke-Sultan William Karameikos was crewed by zero level nobodies... Who were then swiftly dispatched by the furious Sir Bravery, William's elder son, in a rage worthy of Achilles.
Bill also lost his level 8 Dragonborn Fighter Drakonok to a horde of mook orcs a few weeks ago - turns out that in 5e challenging an entire orc tribe to battle is not such a great idea. Mind you when Drakonok's companions (who had fled the orc horde summoned by Drakonok's roared challenge) came back across the scene an hour or so later, the breath-frozen, stabbed, and arrow-pierced orc bodies were piled high in the corridors of Stonehell.
IME very high level PCs in sandbox open game tend to get played less often; they tend to be focused on political shenanigans rather than adventuring, and the player will start to spend more time with their lower level PCs adventuring in lower level parties. Eg in my Wilderlands currently one player has PCs of levels 5, 9 & 20, another has 4, 5 and 17, a third has 5 & 13. A 4th or 5th level PC can adventure with third or eighth level PCs, an 8th level can adventure with 5th or 13th, but very high level characters tend to dominate too much, aren't challenged by most adventures, & often have better things to do.
One thing I learned running an open sandbox campaign was to limit PC starting level; I settled on 8th as the maximum starting level, being the high end of what feels like mid-level in 5e. It doesn't work letting everyone roll up new 20th level PCs just because one guy got a character to 20th. Characters need to feel organically part of the world, and keeping them to 8th initially ensures that.
I find the more PCs are independent entities, not just part of The Party gestalt, the more roleplaying I see, and the more interesting interpersonal relationships form among the PCs.
I like doing online solo high level political stuff, and some PCs like Hakeem the Conanesque barbarian PC are great to GM solo. Mostly though for tabletop I greatly prefer GMing a group, ideally 3+ players; these days I tend to feel a bit awkward running solo games, and there is the lack of player-player interaction sparking new stuff.
This is only a meaningful question in single-party campaigns, especially linear ones with one goal. My Wilderlands sandbox has lots of different PC groups and a TPK would not be an issue; TPK of a very high level group probably means a big victory for some bad guys (or good guys!) but the world goes on.
In a single-party campaign, the group wipes, I may use that setting again later. Again BBEG victory will change the campaign world but it likely is still useable. I certainly won't fudge to keep them alive. It makes the game meaningless if the PCs can't lose.
In multi-PC games it's very common to retire or semi-retire the high level ones. Eg in my Wilderlands Hakeem Godslayer defeated the Black Sun, reached 20th level, founded the Empire of Altanis-Nerath. He's now basically retired from play, the player has a 5th & a 9th level PC for regular adventuring.
In an Adventure Path type game everyone plays the same one PC to the end of the campaign.
I've done it a couple times recently - one group TPKs, another group starts off in the post-TPK milieu - but in both cases it was a couple years later IRL with new players as well as new PCs. Both times it made for a stronger campaign IMO; the new players were never in any doubt that failure was an option.
The two cases I recall:
1. Rise of the Runelords AP - PCs were wiped out by Nualia at the end of Book 1 ca level 4, resulting in the destruction of Sandpoint town, the intended home base for the campaign. Years later Sandpoint was a goblin-infested charred ruin. Eventually the Black Dogs mercenary company was hired by Titus Scarnetti, one of the few survivors of Sandpoint, to clear the ruins - this went on mostly in the background of the new campaign though the new PCs did interact with Titus; Quillax the Druidess even delivered his wife's baby and ensured the child was born without the taint of Lamashtu (his wife & daughter had been captured by Nualia's Lamashtu ("mother of monsters") cult but ransomed back, so there was a fear they could have been infected).
2. My Wilderlands - catastrophic PC defeat at 10th level, in the final battle the lead PC Varek Tigerclaw fell in the doomed defence of Bisgen town against the Necromancers of the Black Sun; leading to the rise of the evil Empire of Neo-Nerath. Subsequent PCs spent years battling the Black Sun as it embarked on a genocidal campaign of conquest; at one point the new hero Hakeem Greywolf battled Varek Tigerclaw, now a Death Knight of the Black Sun - and ripped out his black diamond heart.
Varek at that stage was a soulless husk of a Death Knight controlled by Borritt Crowfinger, NPC Necromancer & Prince of the Black Sun. So GM-controlled.
In "Burnt Offferings" the encounter with Nualia in Thistletop as written is a death trap. There's a narrow 5' tunnel with a pit trap/portcullis, it's perfect for a tough fighter like her to cut through the PCs 1-1. I was using 1e ADnD; the group hit the pit trap/portcullis (one PC* got his foot severed!), then got attacked by the yeth hounds & Nualia while disrupted, and were slaughtered. When I played it myself (in Pathfinder) the GM would have TPK'd us too, if he hadn't fudged massively, letting us flee then come back and redo the encounter (with Nualia still just sitting there, yuck) now with optimised tactics. Second time round my Cleric used 'Command' to force Nualia to come to us out of the kill zone, where we could deal with her.
*An unfortunate Paladin.
I rem once in the early '90s Mortis Deathlord, a ca 25th level 1e AD&D PC in service to demon prince Graz'zt, was trekking through the mountains along with two similar level NPCs, on their way to assassinate the enemy King of Trafalgis, a viking realm. I rolled up a random encounter with 4 adult red dragons, who proceeded to wipe out these epic villain characters.
It was definitely bathetic - and AIR I did have the PC resurrected some years later to continue service to his dark master. But the old stories have loads of bathetic ends. Jack Vance is inspirational. The PC Mortis was ultimately executed by Graz'zt when he (a) started to get cocky, beginning to see himself as Graz'zt's equal, and (b) accidentally violated a non-aggression pact Graz'zt had with Thrin, a lesser god lawful good PC.
If this happens I'll generally do the rolls at-table so players can see what happens. Many D&D versions make it hard to take out a high level PC at table.
I don't make assassins omniscient. I recall one time a Neo-Nerath assassin struck as the ca 10th level PCs were resting at a mage conclave on their way to close the Black Sun gate. With the PC group was an NPC (from The Licheway, I recall) who claimed to be an Archmage, he dressed the part but was really a phony, a 2 hd non-caster. Anyway, when the Black Sun assassin was choosing his target, naturally his top priority was to take out the enemy Archmage... ...And the PCs slept peacefully all night.
I generally find player characters with powerful enemies do take precautions, and aside from 3e/Pathfinder I can usually have those precautions be effective, or dice for it (3e/PF is broken IME and often requires handwavium why high level caster NPCs don't use scry-and-die on the PCs). I recall one serious assassination attempt - the PCs were in Ahyf, local hive of scum and villainy, and got into a big fight at the fighting pits liberating some pit fighters. Hakeem was badly wounded killing Gorok Halfogre the pitmaster, giving three Black Sun assassins who had infiltrated the town a chance to strike when he & his friends fled town. It resulted in a brutal night battle on the road but the PCs managed to prevail and took shelter in a farmhouse, fearing more assassins.
If Hakeem or similar high-value PC was foolish enough to put themselves in a position where an assassin could strike as they slept, I would roll with it, using the 5e rules they would take a critical hit in damage, plus poison - likely would kill a Wizard PC or similar squishy, but a high level Barbarian or similar might well survive the wound, wake up and kill their attacker. It would take a lot of CR 8 Assassins to take out Hakeem, 20th level Barbarian with 2 Epic Boons inc Epic Fortitude, CON 24 & 325 hp (takes half damage from weapons while Raging, so effective 650!). My son Bill's Dragonborn Barb-17 Shieldbiter with 209 hp might be more vulnerable, but generally it's the high level casters who really need to worry.
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