It's not his responsibility to point out Apple's flaws by hacking their servers. The correct approach would be to speak with Apple first and let them handle it. If they don't want to fix it it's their problem. If he gets prosecuted, it's his fault.
It's the ecosystem. People are already invested in their apps, movies, music and photos. There are few people willing to start fresh with Microsofts ecosystem.
Apple knew what they were doing and it worked.