he wasn't suggesting that he'd help him escape the country or avoid his sentence. More likely he was suggesting he could help him with his original question - how to keep his business running. Business emails are moderately sensitive, but most people don't seem to have a problem trusting google (and so the NSA) with that type of information.

Does it really matter what email provider you use if you don't use encryption? I'm not sure i understand why using gmail is any different then sending clear-text emails across the Internet to another provider.