If the Sox stay in the hunt, they cetainly cannot trade Duran. He is a big part of their limited offense.
If they are 10 games out of the third wild card in July, then what?
Obviously they will try to move as many potential free agents as they can - Jansen, O'Neill, Martin, Pivetta. They probably won't be able to move them all, but they will probably try.
But if some team does make an intriguing offer for Duran, do you hold? We've seen controllable outfielders get some fairly impressive returns. i remember when Adam Eaton was traded on his team-friendly contract to the Nationals for Lucas Giolito, Reynaldo Lopez and Dane Dunning. That's a franchise-altering return. If the Sox can get such a return, should they do it? The other option is to keep Duran for his last 3 seasons, which doesn't look like such a bad option either...