Thanks to some of the fine people here on OtM, I've come around a bit to look into UZR, WAR, etc and get a longer view of players value.  

That leads me to the position that Holliday should be the #1 priority for the Sox, even if it becomes a bidding war.  Holliday is similar to healthier J.D. Drew in that he provides the team with solid all around value for his position.

He can be as dangerous or more dangerous a hitter in the Sox line up then Bay.

He improves the defense in LF.

He is the best LF option this year, and arguably over the next 3 yrs.

There is not a lot of power in the Sox organization right now, and not a lot of power bats in the MLB who play plus OF defense.

So if you can acquire the best LF option for this year and the next few, what is that worth?  

Is $18-20m over 5 yrs too much to consider?   When you consider Bay likely will be around $13-15m for 4, and that likely his last two years will carry significant decline from an already lesser team value - I'm not sure it is.

If you sign Holliday, your high this year but have a lot coming off the books next year.  I believe the Sox can sustain that.  You lose draft picks, but would gain them back when Bay signs.   You are taking the best bat off the market in a position of need of both the Angels and Yankees.

So I guess the question is at what point does Holliday become too expensive for what he brings?