Excellent post.
Here's a look at Theo's drafts with the Sox:
2004: (lost 1st round pick for signing Foulke)
Pedey (2nd rd)
2005: (6 comp picks for losing Pedro, DLowe and OCab/lost own 1st rd'er for signing Renteria)
1st Rd Comps: Ellsbury & Hansen
Supp Rd Comps: Buch, Lowrie, Bowden & Egan
2006:
27th pick Jason Place
Supp picks: Kris Johnson, Caleb Clay & Aaron Bates
2nd Rd (71) Masterson
2007: (lost 1st rd for signing Julio Lugo)
Supp picks: Hagadone & Ryan Dent
5th rd Middy & 6th rd Rizzo
2008:
30th Casey Kelly
Supp: Bryan Price & S Fife
5th Westmoreland & 9th Vazquez
2009:
28th Reymond Fuentes
2nd Alex Wilson
2010: (Lost 1st rd by signing Lackey)
Comp pick: Vitek
Supp: Brentz, Ranaudo & Workman
2011: (Lost top pick by signing Crawford)
Comp picks: 19th Barnes (VMart), 26th Swihart (Beltre), 36th Owens (VMart) & JBJ (Beltre)
5th rd. Betts
Theo also signed these international FAs:
2004: Doubront
2005: Dice-K & Okajima
2008: Tazawa
2009: Bogey, Iggy, Montas
2010: J Aro
2011: Margot, Lin