He's not the least bit interesting to listen to and nobody likes him, so a career in media is going to require starting from the bottom. Is that more enjoyable than playing baseball? If he wants to coach he'll have to start at the college or minor league level. Is that more enjoyable than playing baseball? Writing a book or motivational speaker are probably extremely unlikely future jobs for Mark Prior. You don't have to MC Hammer away your money to not be able to live off a 5 year career where you made $12m. Taxes, lawyer/agent fees, family requests, personal expenses, buying a house and just generally living the life of a major leaguer is going to leave you with a nest egg that almost certainly won't come close to allowing you to live like a 1%er for the next 70 years. No amount of appearance fees from Just Ducky are going to allow you to coast through life.