The discussion is all hypothetical about what he would receive (long term or short term). Since we being hypothetical, if his best offer was $300/10 yrs (with opt outs) I could see him accepting accepting $200 million/5 yrs (with opt outs) and hitting FA again at 28/29 years old when salaries have increased with new money floating around (i.e. Cubs network). I get that the millions make it harder to understand, but without knowing your income, if your boss guaranteed you that you’d make $100k per year pretty much no matter what for 10 years, and then another company offered you $133k per year for 4 years, would you really consider the second offer if the jobs were the same? Yes, no question. But that job won't become unhaveable when I turn 40, so not a real comparison.