Recurring Bosses

I was wondering how often people do recurring bosses and what would be the best way to include them? I was mostly wondering that because I had the idea of a boss who pops up now and again and mostly just gets away to get stronger and come back. Maybe my players eventually kill him (or the first time he pops up), or he decides he doesn’t want to be evil and help the players in some way. Either way, what do you all think about it?

I think it is something that can certainly work and the boss doesn’t even have to show up each time in person. Depending on setting, can appear as a voice, as an image on a screen, in a scrying pool, behind an impassable barrier, etc etc.

Maybe they just show up to discourage them and cackle with glee as they send minions. Maybe they only ever talk to them. All things can work, just depends on the narrative and how it makes sense.

I actually had a recurring guy in my first ever campaign. He was very interested in the cleric, and sent some skeletons to fight them the first time and jumped through a portal. He ended up being the cleric’s Uncle, and was trying to make him stronger as well as bring him under his wing eventually.

Things ended up happening, and the Uncle assecended to be a minor god of the world who was the patron of a lot of the … friendly undead of the world.

So what is fun and makes sense for your world and your players is the key.


It seems like a really good idea, story-telling wise. If the bad guy wants to befriend your players, and be useful to them, it can make for some good stories. Your players could have conflicting emotions about the individual.

Is the usually-evil-boss really trustworthy now? Will we get backstabbed?
Who knows! Maybe the bad guy is only bluffing and is still the bad guy.

The story @Great_Moustache told us is good, since the players got invested (I suppose?) in the evil person and the ever growing boss probably had a serious impact on the story.

Anyway, I’m blabbering here but it seems like a good idea.

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I’ve ran quite a few campaigns with reoccurring villains and I highly encourage it, because that way the PCs relate to the antagonist, even if it’s only to direct their anger and hatred towards someone. The problem you left your scenario very vague, so it’s hard to give any real advice on it, but I’ll give you a couple of general advice, through two of my own examples:

  • I ran a city campaign where the newly appointed mayor was a tyrant and the PCs actually got to meet him in the first session, when he spoke his balcony to the people. Over time they witnessed more speeches about raising taxes and draconian punishment of the population and later as they rose in power he even invited them to a banquet and a masquerade, etc. That way he was a constant presence, even if he was for the longest time out of the reach of their grasp.

  • In another campaign, one of the mid-tier villains was actually the guy who hired the group in the first place, but he was a devil worshipper, so he planned to sacrifice their souls at some point and as he kept them close, the group slowly but surely got more and more the feeling that something was off about him, so their distrust kept on building up, but they were never sure what he was up to.

One general advice I can give you though, is to not throw the big evil threat to early at the party, because if they get the sense that they could defeat him at such an early stage, than it takes the aura of danger from the antagonist. Just let him/her watch the PCs fight some of his minions and goons, while mocking them or throwing them off from time to time to challenge them, but don’t have the antagonist commit early as it might feel anti-climatic.

Although, if you want to have the PCs fight the antagonist early on, then maybe present the antagonist or a group of antagonists as a rival who proceed along the same route as the PCs, trying to achieve similar things, but with different philosophical or morale views on how to achieve that goal. Just make sure that the rivals don’t show up too often, because else they might develop a “Team Rocket Syndrome” and they’ll become a joke, as the rivals get defeated over and over.

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The setting I’m working with is a remote tropical island in the middle of the Caribbean where the PCs are college students who are trying to find a way off the island. The recurring villain is an animal tamer and big game hunter who works for the organization on the island. Perhaps the best way for him to be recurring is if he brings some “exotic pets” to their base of operations every once in a while to make a statement and leaves the PCs to deal with the strange creatures. Perhaps if he does fight, he only hangs around for a couple rounds before getting bored and just leaving. I’m not sure what would be the best way to do this…

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Firstly, I would have them meet the hunter really early on, in a non-threatening situation. Just have them talk to him, maybe he even tries to recruit them, but make him feel slightly antagonistic, for example a bit cocky and arrogant. Then I would probably have him not show up for a little, but still have the PCs confronted with his actions, maybe running into some of his hunters or one of PCs stepping into one of his animal traps. That way you establish an indirect presence.

After that, you could have the first real confrontation, where he just sends some of his animals after the PCs to chase the PCs away, while he takes the backseat and just observes. That serves to show his power, but more importantly he can gather information on how the PCs fight and what tactics they use, so he can prepare for eventual encounters later down the line.

These are obviously just my ideas and how I would handle it, but I hope they are to some use to you.


Game masters stash has just posted about this subject right here, on facebook.

What a coinkidenk!

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