This long of a contract, at this price, for a guy as young as Cabrera Do you prefer older players sign long contracts? I don't see how this is going to get us to the scenario you are seeing. For someone like Fielder with Boras as an agent, it seems likely that he isn't interested in a long term contract anyway, so this wouldn't have an impact. If you're talking about someone line Braun, it is in a team's interest to sign a player to a deal like this, to avoid rising arbitration costs. If you're talking about a player like Hardy, the team has a replacement for him in the system down the road, and if he raises a stink, he'll see himself traded or non-tendered when the time comes. I guess it depends on where the team is. For the Orioles, they traded Bedard away 2 years from FA, but they didn't do it only because of money. They did it to get a younger player who will be a better fit for the next time the Orioles are competitive (whenever that may be).