The players in my campaign want to go up against a noble family that's been dealing with a particularly high ranking contract devil. When they reach him, I want to be ready to offer them a deal, and even if they decide to reject any of the devil's offers out of hand they'll certainly want to get to the bottom of the contracts the family has already signed.

The trope of a contract that hides some nasty surprises behind a maze of clauses, conditions, legalese, and loopholes is a time-honored one, and a Contract Devil ought to be able to cook up a particularly tangled and self-serving one. But not being a contract lawyer myself, it's rather difficult to actually draw up such a contract, and I don't think anyone at the table really wants to sit through the iTunes terms and conditions mid-session either.

Last time they tangled with Mr. Mephistopheles, I asked the player being offered the deal to make linguistics and knowledge (nobility) checks to try and penetrate the legalese and figure out what's under the surface - but he didn't seem to be a big fan (as a player, not a character) of not being allowed to hear the actual terms he was signing onto. How can I present a contract that feels authentically complex, in a way that doesn't make the players feel like they're deprived of their agency, without actually drawing up said contract myself?

  • \$\begingroup\$ Do you want this to be a challenge for the players, or their characters? What skill should be required to overcome the challenge? \$\endgroup\$
    – Superbest
    Jul 8, 2016 at 5:25
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    \$\begingroup\$ When faced with a somewhat similar situation, I asked my sister - a real-life lawyer - to cook up a contract to me, as the devil. She dropped a 250-page tome on my desk a few days later, with a huge smile on her face, saying "Now, that was FUN". \$\endgroup\$
    – T. Sar
    Jul 8, 2016 at 17:08

5 Answers 5


If the minutiae of labyrinthine legalese doesn't sound like fun to you, and it doesn't sound like fun to the players, then don't use it. Your player is right -- it's not fair to agree to a contract without getting to hear the details.

Instead, offer deals that are tempting, but dangerous.

Let's say the party has a question for Mr. Mephistopheles -- they want to know which of the nobles summoned the demon. His response:

All right, my little mortal friends. I'll tell you which nobleman called me up. In fact, I'll tell you the name of each and every one of these nobles and their role in their plot.

But that information comes at a cost. If you accept, someone who thinks highly of you now will come to believe that you are all in the employ of a demon.

So, do we have a deal?

The offer is clear -- there's no trickery hidden in the language, no secret clause the players don't get to know about. If they need to ask clarifying questions, Mr. Mephistopheles is happy to explain further.

In the end, it's a tempting, but dangerous offer. Information about the nobles' plot would be very valuable. The party could use it to bring down the evil nobles and achieve their objectives.

But at some unknown time in the future, the party will pay a serious cost. Maybe the king will decide to send demon-hunters after the party. Maybe the head of the church will excommunicate the party's cleric. Maybe a rival leader will turn against the party in the middle of peace negotiations. And when it happens, Mr. Mephistopheles will be there to offer another deal.

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    \$\begingroup\$ did you write "demon" instead of "devil" or was it intentional ? \$\endgroup\$ Jul 8, 2016 at 12:07
  • \$\begingroup\$ This is how I do these things now a days. No matter how much time you put into writing something like a contract out it won't live up to your expectations. It will either omit something you intended or will leave too many loopholes that a devil would have seen before committing to the page. \$\endgroup\$
    – Slagmoth
    Jul 8, 2016 at 13:23
  • \$\begingroup\$ @AnneAunyme, it looks like I did. The difference wasn't intentional. \$\endgroup\$
    – Joe
    Jul 8, 2016 at 21:04

If you have time to spend on this, you can ask the players to write the contract themselves. As neither your players nor their characters are in-real-life lawyers you can bet there will be plenty of loopholes the devil will be able to exploit. They can make checks if they want, and it could give them clues like "you mentioned you didn't want you soul to be sold, but forgot to precise you don't want it given for free too".

Be ready for a long discussion between your players about what to write exactly. If the situation requires to be fast you can make time past when they are talking, and make the devil smile innocently as he reminds them about the time flowing.

The devil may ask for some minor modification, that apparently doesn't change anything. It could be to insert a real loophole in his favor, to make disappear one which is against his interest, or just bluff. The haggle can last for as long as you wish, but don't make it last too much or players will be bored.


Expand the Current Process

Legal labyrinths are fun, but the more realism involved, the more games get bogged down.

Perhaps, rather than representing the process with a single roll, a series of rolls would suffice. These checks would be built in such a way as to reveal progressively more about the risks involved with the contract.

Some skills, such as Sense Motive, may be useful throughout, but try to vary the required skills for each section so that different characters and attributes are useful in different phases.

For greater results, have the players declare which skill they are using and use different charts for each skill, allowing differing levels of disclosure. You could even make the individual snippets of the contract (gathered through successful checks) on little slips of paper, thus letting the players "read between the lines" after the necessary skill checks are made.


Opening Clause

(We, the adventurers, heretofore known as THE PARTY, agree to...)

Skills: Knowledge: Religion, Knowledge: Nobility, Bluff, Sense Motive

Check Result:

10+: This section is setting out who is involved in the deal and what the penalties are for breach of contract. You don't see anything too shady here.

15+: Some of the wording here is a little suspect. You see that the contract devil has set up a situation where he will not need to fulfill the contract if the party actively opposes the chain devil's other interests.

20+: [Appropriate party member] is actually entitled to 20% less recompense due to certain clauses in the contract. This portion goes to the contract devil, for 'services rendered in or around a twenty year period preceding or following the signing of this contract.'

Provided Services

(Mr. Mephistopholes, hereafter THE CONTRACTOR, does hereby agree save in the events outlined in SECTION I, to provide the following services....)

Skills: Sense Motive, Knowledge: Local, Knowledge: Nature

10+: The devil is offering to provide you information pertinent to your quest along with the opportunity for future business deals at preferred rates.

15+: There are some problems with this. There is no guarantee that the provided information is unknown to you, for instance.

20+: The devil is offering some services that are couched as beneficial but may not be. 'THE PARTY shall be protected from transgressions or contact with nonsentient natural flora to a radius of 1000 feet at all times for a period of six years.'

Provided Compensation

(THE PARTY agrees upon evidence of fulfilled contract to render unto CONTRACTOR the following...)

Skills: Sense Motive, Knowledge: Arcana, Athletics

10+: The devil is requiring you to travel to an undisclosed location of "appropriate combative risk" to recover an item. The item is guaranteed to have no living owner.

15+: The item appears to be cursed, though not fatally. There is also no guarantee that the item doesn't have an undead owner.

20+: The area in question appears to be extremely dangerous for reasons other than local monsters. Some clauses mention obscure climbing terms that indicate only an expert athlete would be able to pass.


The trope of a contract that hides some nasty surprises behind a maze of clauses, conditions, legalese, and loopholes is a time-honored one

So is the one of a maddeningly simple "contract" which becomes a nasty surprise or series of them because of things the other party isn't aware of or can't see at the time they signed it. Think about Faerie shenanigans in Irish literature or the Oracles of Greek mythology. The traps are very simply presented but hard to perceive before it's too late. The deception isn't in a maze of legalese, it's in the advantage the presenter holds at the time they offer a seemingly simple and uncomplicated set of terms.

The way to make this fun (if the entire premise actually does seem like it'll be any fun at all) is to keep the contract as simple as possible, and surround the contract with situations, facts, knowledge, conditions, or other in-world realities which the devil knows about but the players (or their characters) don't, which will soon be revealed if the players commit. Dun dun DUNNN...

However. That's all contingent on two things:

  • Is it going to be fun for you to arrange all this? It will take almost as much creativity as an actual worded contract. You're just moving the perils out of the contract contents and into the unwritten game world.
  • Is it going to be fun for the players, to anticipate that the maddeningly simple contract is going to spank them if they accept it?

Other things to consider:

  • maybe fun can be had in allowing the players to "win" at this one, if they manage to do so. If they figure out the pitfalls by learning what they are while they consider the contract and maybe have their characters ask pointed questions about the circumstances, maybe that's good for them and the game moves on.
  • maybe really force them to roleplay their characters, if you try it this way and the players themselves figure it out. The player has read Macbeth, but is their character worldly, literate and intelligent enough to know that "no man of woman born" excludes those who came in to the world via <spoiler redacted>? Consider making them roll for it and roleplaying the results.
  • \$\begingroup\$ Moving the complexity of the contract from the legal part of the document itself to the complexities of the world itself is a very good point. Most GMs are much better at worldbuilding than contract law. Forcing players not to be too savvy about it seems like a bad route for me to try though, given the poor reaction to perceived loss of agency my player had the first time. They're a pretty brainy group, and generally don't enjoy having to "dumb down" for their characters. \$\endgroup\$ Jul 8, 2016 at 20:54
  • \$\begingroup\$ I'm not advocating for removing agency. Full agency is involved with letting players play their characters' stats and skills. But I did present it as something to consider, and it's a strong contrast against the other option I presented, which was "let the players do it" (and potentially win it) regardless of how much roleplay sense you and your table want it to make. Players tend not to be dumber than their characters. \$\endgroup\$
    – Beanluc
    Jul 8, 2016 at 22:43

Have the player make the check like you did, only this time its a secret check. Then you give the player information based on what they have deduced much like a knowledge check for a monster. The better the check, the better an understanding of it you have. Let some of the contracts have something very tricky in it to produce a higher DC as well for those ones if you want to lead them somewhere or something.

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    \$\begingroup\$ This is pretty much exactly what the querent tried already, which is what they're looking for alternatives to. \$\endgroup\$
    – Miniman
    Jul 8, 2016 at 6:15
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    \$\begingroup\$ If anything, making the roll in secret is only going to reduce the OP player's sense of agency even further. \$\endgroup\$
    – abza
    Jul 8, 2016 at 6:21

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