I think Isaac would have a blast getting pissed off about how unhelpfully helpful Coriolanus is. :D It would be like Doakes and Dexter, but with less hatred and more 'Goddammit Cheshire can you not?' -_-
Oh, I can imagine the on-field scenario now:
"There's a little birdie above you, Grizzly Adams."
"What? The hell is that supposed to—*alarms set off*"
"Fly on the wall. The walls have eyes. Honestly, I'm saying it clear as the night sky *huffs* This is un-bear-able. These conditions are simply grizzly in comparison. Insufferable."
"CAN ANYONE TRANSLATE?! FOR THE LOVE OF ALMIGHTY GOD."
Yes. They'll make the best-worst team ever.
But, I can certainly imagine the relationships currently:
Cheshire definitely uses Hook purely for his dashing looks.
@Autumn_Burns_Red
He and Mor'du have an intense love-hate relationship whenever they're on missions. Apparently, Cheshire is more comfortable over the mic than in person. In person, Isaac is far too intimidating to poke fun at as much as he does when providing intel. Lol.
I'm certain he and Maleficent have a very tit-for-tat relationship, if that's okay. Kind of clever, non-hostile jests they continuously throw at each other. Kind of their way of communicating.
@Shattered♦Secrets™
As for Jack, I think Cheshire treats him much like the actual Cheshire treats Alice, if that makes any sense at all. Drawn to the loners and outcasts, I suppose.
@Chromatic
These are just suggestions, though, feel free to add if you guys wish.