When you factor in the time value of money I agree 30, 30, 12, 12, 12 is about the same as 20 * 5. However, you might as well look at it as 2 years at 30 with the potential downside of another 12, 12, 12 for a bad pitcher. If he does not elect free agency after 2 years his value will have declined substantially. That would be the only reason why he would not elect free agency again after 2 years. You might as well look at your contract idea as a 2 year premium contract if he performs well and a 5 year bad contract if he doesn't. That is not a good way to do business.