A realistic offseason? Realistically I do not think the Sox will be in on signing Cole or Strasburg. Whether they play the games to string fans along like last year, who knows?
Realistically I think they target a pitcher that they like, let's say it is Wheeler. The Sox could offer him a good deal quickly and lock him up early in the free agent season. This is what they did with Zach Duke back in 2014. While everyone was looking at Andrew Miller, the Sox targeted the perceived second best left handed reliever on the market in Duke and signed him by mid November.