Annie is slightly too old to have been taught by him, and if I calculate correctly she'd have left the Deck before he arrived anyway. And Leigh came to the Deck too late and is too old now. But he'd probably know her as Eileen's Diamond friend. And so far she's been going to the public school because what's good for everyone else is good enough for an Ace's ward it encourages her to mingle with others, so he might have seen her occasionally on the small campus.