I think he understands it just fine. He calculates the cost/benefit ratio of trying something whether it's legal or not. If it works, great for him! If it do

I think he understands it just fine. He calculates the cost/benefit ratio of trying something whether it's legal or not. If it works, great for him! If it doesn't work, oh well, it costs him a few extra dollars. Just like trying to back out of the buyout. Most people are easily intimidated by legal-sounding crap, like a severance agreement written up by company lawyers. In my experience, most lawyers are crap (I have had 1 good one out of around 5)and a lot of the "legal agreements" being written have illegal stuff in them, which is why they always say "if anything in this contract is found to be illegal, the rest of it still holds". The advice to consult with a lawyer and maybe an accountant is IMO well worth the extra trouble and expense. They're counting on employees being too intimidated to do it.