To me it kind of makes more sense for a team with a smaller payroll like the Royals to employ such a strategy. For a team with one of the highest payrolls to do it still seems wonky to me.
Even if the Red Sox wanted to trade Ortiz, who would they trade him to? I'm pretty sure the vesting option goes with him, so it would have to be a contending AL team with money, other than the Yankees. That leaves the Angels, maybe the Jays.
Here's a little factoid someone posted on the Globe forum.
During the Epstein years the Sox had a guy named Craig Shipley who was heavily involved in the international scouting. Shipley signed Iglesias, Tazawa and Bogaerts.
One of the first things Ben did as GM was fire Shipley.
I don't think there was an automatic assumption. A strong hope, yes.
It's like the Lester situation. Most people figure we could have signed him for 6 years, 110-120 million before the 2014 season started. He had a good year and ended up with 155 million.
Overpaid on the salary in return for a cut on the years. If he had a good year he would've gotten 6 years in FA.
It was a bet, really. So far a losing one.