Ah. That's a problem. Strange visibly winces as Billie mentions pissing off the city guard.

"Good gods, you really were a delinquent." There's no judgement in that statement, it's just Strange pointing out what he thinks is the obvious. Though really, that explains a lot. Delinquent child Billie, falling in with a bad gang, becoming a pirate. Pity about all that, but it's not like he can do anything to change her situation.