The Red Sox began the process of drafting Brandon Workman and Anthony Ranaudo before the two were even born. No, their coming wasn't told in the prophecies stored in the deepest, dankest regions of Fenway Park, but the first move that eventually led to their acquisition came in 1986 -- Workman was a 1988 baby, and Ranaudo 1989. The whole process has been documented by Grantland's Ben Lindbergh, who figured out the lengthiest active transaction tree for all 30 teams. The Red Sox have the third-longest, thanks to a move made in 1986 that eventually led to both of Workman and Ranaudo coming to Boston.
It all started with Ken Ryan, whom the Sox signed as an amateur free agent on June 16, 1986. Ryan was traded a decade later for Heathcliff Slocumb, who was moved in 1997 at the trade deadline to bring back Derek Lowe (as well as Jason Varitek) in a deal that any Red Sox fan conscious at the time remembers well. Lowe left as a free agent after 2004, bringing the Sox the compensation pick that they used on Craig Hansen in the 2005 draft, and Hansen was sent to the Pirates for Jason Bay in the summer of '08. Bay left for the Mets following the 2009 season, and left two compensation draft picks behind, compensation picks the Sox would then use on the stars of this little tale, Anthony Ranaudo and Brandon Workman.
Lindbergh's piece features a nifty little flowchart of all of that for you, if that block of text is too much or you just love pictures. (I love pictures.)
You should absolutely check out the whole thing, and not just because there are somehow two active transaction trees longer than this one.