In the recent Boston radio interview, Theo followed his discussion about the value of the Cubs second round pick--under the new cba--with a discussion of when giving up a high pick might be worth doing depending on the value of the free agent (without mentioning any names of course).
My impression is that he might sign a guy like Bourn if the value was right for the Cubs.
Off-season timing is significant. Nationals were interested in Bourn at the beginning of the off-season but instead traded for a lesser player, Denard Span. Span, one year younger than Bourn, is kind of a similar offensive player--aside from the speed factor--and a lesser defensive player. Nats control Span for three seasons at about $20 total. But, Nats had to give up their top pitching prospect, Alex Meyer, who has more value than the second round pick Cubs would have to give up for Bourn. At the time that Nats traded for Span, Bourn's asking price was more than the 5/75 deal that Upton got from the Braves.
Seems likely that Bourn will end up getting less than $75. What if Cubs could sign him for the 4/52 Edwin Jackson deal? Is that the kind of value that Theo might think worth giving up the second round pick? Or, is Theo thinking three years tops, if that?
I don't see a problem with Bourn blocking B. Jackson. All the other current Cubs OFers, including the high and mid-level minors, are expendable. Don't see a problem finding two OF spots for the next few years. Indeed, if you can get sufficient offense, the more legit defensive CFers in the OF the better.
Of course, Boras tends to pull a rabbit out of a hit at the last minute, so likely that the Bourn market does not bottom out all that much. Even possible that Bourn returns to the Braves.