First, Gary's been a bit stupid for poking around those systems, especially in today's climate. I'm pretty sure he knows this and I'm quite sure he's unlikely to repeat the offense.
I woudn't trust the US Justice system. Currently in the "War Against Terror" we've got a lot of ambitious prosecutors and law enforcement personel chasing a handful of potential defendants. In this climate anyone who falls into their clutches is potentially in big trouble regardless of the severity of their offense. Zacarias Moussaoui was peripherally connected to the 9/11 hijackers -- he was in jail at the time on an unrelated matter -- but they are going to execute him for the offense of not liking Americans and "lying to the FBI" (yes, its a real offense, that's what they got Martha Stewart on when they couldn't find solid evidence of criminal conduct). More realistically, the case in Lodi in Northern California is closer to what Gary's facing -- nothing or trivia will get parlayed into someone serving 39 years.
I doubt that Gary will end up in Cuba but he may end up in a maximum security jail, which to all intents and purposes will be the same thing.
I'd advise Gary to keep well clear of the US until saner times.
PS. I am a citizen.......yes we know what's going on, yes we can't do that much about it at the moment (but its not for a lack of trying).