Points you might want to be aware of: a freed slave (who has to be over 30, if this is an issue) is almost but not exactly identical to a freeborn citizen, in terms of rights -- they can't hold political office, and they can't join the army. So if you want him spying, he can't actually be doing it in affiliation with the Roman military. I don't know if this presents a problem, but I thought I would mention.
If it helps, also, his master (assuming he's a senator/equestrian) would be at least bilingual in Greek (it was a prestige language for the Roman elite; they liked to have Greeks as secretaries and whatnot), and it looks like, judging by the war maps, that a lot of the fighting was in the south (IIRC, the south was definitely part of Magna Graecia) and Campania (has a lot of cities that were formerly Greek colonies, like Neapolis/Naples, which is why its name is Greek).
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If it helps, also, his master (assuming he's a senator/equestrian) would be at least bilingual in Greek (it was a prestige language for the Roman elite; they liked to have Greeks as secretaries and whatnot), and it looks like, judging by the war maps, that a lot of the fighting was in the south (IIRC, the south was definitely part of Magna Graecia) and Campania (has a lot of cities that were formerly Greek colonies, like Neapolis/Naples, which is why its name is Greek).