If you assume he doesn't decline by the time he turns 26: he is a much better player and 5 years younger at FA time than Robinson Cano who got $240. Clayton Kershaw turned down $300M, and Trout is inherently worth more on a long term deal as a position player. In todays dollars, I think Trout would get $350M. Adjusted for inflation, that will be just over $400M. We'll have to wait and see though. In addition to the TV bubble bursting, there seems to be a bit of a trend to go away from these big deals. The Red Sox won last year by spreading their money around, and it seems like that's what the Yankees want to do this year (if you consider Jacoby Ellsbury and Brian McCann bargains at $263M, anyway). You have to go back to the 2009 Yankees to find a team that really won by buying a superstar, fueled by Derek Jeter and CC Sabathia. There are 4 big contracts out right now: Fielder, Votto, Cano and Pujols. It will be interesting to see if one of those teams wins it next year, although it looks like no one is going to credit the Pujols or Fielder contracts as a contributing factor.