I doubt he sleeps well.
It's understandable and enjoyable that we are in his head every waking & sleeping minute.
He honestly won't give a fuck. People in his position never do. They usually go into a company, sack loads of people in the name of restructuring ( Scruffy Jim is a perfect example at the rags) fuck everything up, are given a golden handshake, leave and fall straight into a similar role elsewhere. Rinse and repeat before they retire on a gold plated pension.