Jail? Really? Aren't there better alternatives for cases like this?
Insider trading is basically theft, only with no specific victim, and no broken windows; a very clean crime. Insider trading is stealing from other shareholders, which might include pension funds of HN readers.
Some discussion of impacts of insider trading here - http://money.howstuffworks.com/insider-trading3.htm
You could fine him treble damages or something, but if most of his income derived from insider trading, there's no way to apply the penalty.