It’s unlikely either Sig or Leon have run into DH Cory but it’s definitely possible with all the shenanigans happening between Dalaran and the Broken Shore. If they ever did meet, Sig would ignore the poor bat but Leon would try to be friendly/helpful at least lol. I suspect Cory gets lost a lot lmao HELP HIM.
In the past however, Cory and Sig were probably from the same hometown (Silverbay) and/or the same swath of Eversong coast. They could’ve been aware of each other as familiar faces around town but probably not friends (jk Cory is everyone’s friend whether they know it or not lol). Sig spent much of his growing years working for his dad’s fishing business whereas Cory had a lot more freedom to do whatever, which usually meant being lazy and having fun lol. I doubt either of them would remember each other after so many years, especially not Cory since he can’t remember much anyway.
He remembers sig as that one lobster that this one time