Or he could just live off the Bitcoin? I mean think about it, he can buy gold, silver, lambos, booze, clothes and pretty much whatever he wants. He just needs to not let the tax man see him living too lavishly.
There mightn't even be any potential tax issue in some jurisdictions, such as those without capital gains taxes, but there is certainly the issue of money laundering / use of ill-gotten gains / theft investigation.