It would be really beautiful if he met Lord Kerberous and decided to draw a portrait of him and all his family. Ezayne could be the one bringing them together! :D

[[ Oooooh, that would definitely be interesting! I do love it when poor, I-just-want-to-be-normal Jack gets dragged into the affairs of the powerful and unusual XD If they paid him well enough, though, he’d give them his best work possible. ]]