Many game systems have some form of what is generically called "hero points", which are resources that PCs can spend to significantly improve their odds of a successful action, or in some more powerful versions to bypass a random roll completely and simply achieve success without any risk.
Of course, if you let the heroes in a story use such mechanics, you should also let the major named villains have access to them as well. This gives them a (virtually) guaranteed escape when the heroes close in, which helps turn them from a one-shot adversary into a recurring arch-villain.
You can bet that The Joker has a good stash of "villain points" ready to use to avoid ultimate defeat.
Which inspires an idea: A roleplaying game in which characters can interact directly with game mechanical meta-concepts. A Joker-like supervillain decides to stage a heist to steal a bunch of hero points. If he's successful, then of course he gets the game mechanical benefits of having a ridiculous number of hero points to spend fighting the heroes!
Commentary by memnarch (who has not seen the movie)
Hm, I guess Jim lost that roll then. I suppose Jim could be really putting on a show for Kylo, but I think he's actually gotten brainwashed now. Good try on the technically true statement though.
I do think that Sally might have not made it air-tight enough though. Being loyal to Kylo and the First Order is definitely pretty difficult to work around, but nothing keeps Poe from also being loyal to the Resistance as long as he can jump through the mental hoops well enough to do both. And that's not even getting into what Poe thinks loyalty means for Kylo or the First Order. Is it as simple and straightforward as never killing them or trying to? Is it solely trying to bring about the end goals, in which case Kylo and the Order could be sacrificed in the process if Poe could think of a way to do so.
As for reporting everything he learns about the Resistance, that wouldn't include anything he already knows, so he'd be able to keep the secrets he's currently got unless there's a second brainwashing session. There's also no specified time for when to report, so Poe could theoretically report information selectively as long as he does so eventually. Like, for example, just before it becomes useless or out of date. The question then is, can Jim figure out the loopholes without Sally closing them off first?
Commentary by Keybounce (who has not seen the movie)
"I will be a double agent". That can be true without being Kylo's. So, Force Suggestion.
And a clue to the game system. Spending a Fate point. This mechanic is found in several systems - a limited pool of "Ka manipulation", the ability to make the outcome follow various story tropes, a way to influence dice rolls heavily in your favor, a way to control the "suspension of disbelief" factor.
But there's a system I just found out about where it's actually called Fate points. Not that there might be others.
And... Sally being Sally at the end. Slightly silly.
Kylo Ren: You’ll be my double agent in the Resistance?
Poe: I will be a double agent.
Kylo Ren: Hmm.
Kylo Ren: Force Suggestion. And I’ll spend a Fate point.
GM: Okay... Sally, roll behind my screen. Jim, your save too.
[SFX]: roll roll
GM: Jim, another note.
Kylo Ren: You will be loyal to me and the First Order, and report everything you learn from the Resistance.
Poe: I will be loyal to you and the First Order, and report everything I learn from the Resistance.
Kylo Ren: Now... do the Hokey Pokey and turn yourself around.
Poe: Argh! These restraints!! I caaaan’t!!!
Kylo Ren: And that’s what it’s all about.