He's making far more this season than he would have in any of the seasons under the Met's contract by a considerable amount. 3.25mil is a considerable amount? He gambled $41.75mil for a 7% raise this year....that sounds, less than ideal. Grandal probably breaks even next offseason if he takes the highest offer (probably 3/$40mil). Any issues this year and it was a hefty mistake. He also cited winning and ST location, but I am guessing that was a decision long after the Mets offer when the multi year deals were more like $40mil total where $18mil over one year made more sense. The only way he loses that much money is if he completely falls off a cliff or gets a career ending injury this season. You also fail appreciate the risk of signing a lower annual salary for a longer period of time. He could very well have a monster season this year and get a higher offer next season. If that happens then he would have actually lost money by accepting a lower AAV for more years. What is more likely, him having at a comparable season as he usually has, completely fail or get a career ending injury? It isn't like there isn't a risk of losing money by taking to little money for too many years. Just ask Lucroy.