My 16:
1.Sale of Babe Ruth
2. Tris Speaker for Sam Jones
3. Crawford signing
4. Curt Schilling and B Anderson for Mike Boddiker
5. Bagwell for Anderson
6. Lyle for Cater
7. Lynn & Renko for Tanana and Rudi
8. Bill Lee for Stan Papi
9. Cecil Cooper for G Scott & B Carbo
10. Pablo signing
11. G Scott, Lonborg & Others for Tommy Harper & others
12. Jamie Moyer for Darren Bragg
13. Dave Henderson for Randy Kutcher
14. Freddie Sanchez for Jeff Supan
15. Dice-K signing
16. Renteria signing (I think we ended up paying about $40M for that one year.)
Others...
Offerman? Matt Young? Steve Avery? The Brad Penny/John Smoltz tandem signing for the 2009 season?
Lugo had a decent first year, but injuries turned his fielding from adequate to awful.
The Manny trade brought us Jason Bay, who played well for us. We still have Brentz and Workman as comp picks for losing JBay, but that's not really much.