
Stan is your typical guy who hides his softer feelings under the gruff asshole veneer. The guy who may do something nice for another person, but acts as though he's doing it just to shut them up. He's pretty good at improvising on the fly, and he understands people well enough to get them to shell out money to look at a trout he superglued to a rabbit. He will encourage the youngest member of the team's interest in scamming people, while also trying to protect them if things go wrong. Probably won't be necessary, but he'll do it.
He knows about the supernatural and the weird, even if he pretends not to, so the odder members of this group won't phase him too much. He's also committed a wide array of actual crimes, from stealing nuclear waste, to smuggling pugs across national borders, to tax fraud. Lots of tax fraud.

Of course, Darien then proceeded to go and straight up rob the vault to scratch that itch - and flip Arnaud the bird - then wouldn't give the money to the Official when he demanded it, even if it meant Darien went into Quicksilver Madness. Which happened, because Darien wouldn't back down, either. So Darien is: sneaky, willful, stubborn, and doesn't always think things through.
Fortunately, I don't think Stan is going to dissuade Darien from stealing to his heart's content, as long as it isn't from Stan. Actually, Stan's biggest objection might be if Darien tries to help him win at a casino. Stan might take that as slander against his skills. This would probably have to take place after the end of the series, when Darien doesn't have to worry about Quicksilver Madness, since there's no one on this group that's going to be able to fix that for him. Unless he's moonlighting with this bunch while still working for the Agency, but he's not careful enough to pull that off without Hobbes or the Official figuring it out.

When Toph gets it in her head to do something, or not do something, almost no one has any chance of changing her mind. Like Stan, kind of a gruff asshole. The kind of person who shows affection by punching you in the shoulder. it took her a while to get the hang of being a team player with Team Avatar. Which means it's either going to be a struggle in the early stages with this group as well, or she's learned from her experiences and will embrace teamwork more readily. The rest of the team is adults (more or less), and she hasn't always had the best of luck with adults. Once she demonstrates she can take care of herself, it should be fine. At some point, Stan will ask her to create and animate some stone statues he can market as "terrible rock people" for another attraction. It'll work great until Toph makes them start attacking and fake eating people.
For all that she can be sneaky when she feels like it, Toph usually likes to settle things more directly and loudly. Pick a fight, hit people with rocks, that kind of thing. She and the next member of the team ought to get along like a house on fire.

But, if you can frame it as making bad people miserable by taking the things they cherish most - money - she can probably get into the spirit of it. Especially if she's allowed to incorporate explosions. Between Darien and Stan, I'm not sure which of the two is going to be better able to recognize how dangerous she is. Stan fancies himself a bit of a ladykiller, and while Darien definitely thinks he's charming, I think he's worked with enough dangerous ladies he's not going to make the mistake of underestimating her.
Like I said, though, she and Toph should get along great. Probably hit the limits of their patience for the sneaky stuff or playing nice about the same time. Then it'll be time to break stuff, since no one is going to be able to rein in the two of them at once. Although Fiona might try to rein herself in a little bit with a pre-teen involved. Maybe.

He's a successful businessman, so probably not unaccustomed to questionable practices. He also kept D.B. Cooper's duffel bag full of money after the guy parachuted into his camp, and kept that secret, plus the secret of who Cooper actually was, for decades until he was hauled into court. There's also the fact that he was apparently unfazed by a guy parachuting into his camp and asking to borrow his truck in exchange for a duffel bag full of money.
Totally willing to make wagers with other wealthy men, which is the sort of thing that encourages underhanded tactics. And he's not above being sneaky himself, like when he got his radio station back from Johnny by picking Johnny as the one employee he got to take with him. Anytime you can get your opponent to say, "Well played," you know you made a slick move. Or so I've been taught by popular culture. I'm not sure I've ever gotten someone to tell me that. Perhaps one day.
I'd expect he might want to take the reins, since he might be the richest person on the team - depending on whether Toph has access to her family's fortune. And Jimmy can be intimidating at times, but he's also savvy enough to know when that's a lost cause. So he might be smart enough to realize trying to order around this bunch is a terrible idea. That lets him stay in the background, make his own plans, and he can offer some insights when he thinks it would be helpful. That can be a fun job, to be the one who helps finalize plans, rather than having to come up with them from scratch or make decisions. So much less stressful.
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