Oh, god, the sheriff. That word alone is giving Al migraines all the way from his OU-counterpart.

Yeah, they would probably have had their share of frustrating run-ins in the past. Al would've tried to be amicable and ingratiating right up to the point that Bigby pissed him off, so...likely a somewhat checkered relationship? Al's never going to have been cooperative unless it furthered his interests, but his joint's not one a law-man'd have to worry about his safety in.

(I'm sure that they will get along marvelously in their new environs, though, and that Al will never respond to any dispute with Bigby by asking when the cafeteria last had char-grilled grandma on the menu.)