In mid-2008, the Bucs traded Jason Bay, Xavier Nady, and Damaso Marte for Andy LaRoche, Brandon Moss, Jose Tabata, Craig Hansen, Bryan Morris, Dan McCutchen, Jeff Karstens, and Ross Ohlendorf. Bay and Nady were to be FA at the end of 2009. For Marte there was an option for 2008 with him also eligible to be a FA after 2009. Basically the Bucs traded 3 players who they probably would not have kept after 2009 (maybe Marte after 2008) for 8 prospects.
As of Nov 2010, LaRoche and Moss are gone from the organization. Tabata is starting in LF and Ohlendorf is possibly the Pirates best starter for the last 2 years (yes you can argue about that!). Karstens is also in rotation and has pitched well at times. McCutchen looks like a spot starter and long relief but is not a key player. The other prospects have yet to establish themselves.
If we look at the salaries (some I had to guess at) and WAR for all the players in the trades since they were traded, the totals are:
Players Traded (Bay, Nady, and Marte): $22M for 9.6 WAR in 2 months of 2008 and all of 2009.
Players Obtained: $4.5M for .6 WAR in 2 months of 2008 and all of 2009.
So the Bucs would have won 9 more games (6 in 2008 and 3 in 2009) for ~$18M.
What about draft picks since Bay was a Type A FA? The Red Sox got Bryce Brentz (pick 36) and Brandon Workman (pick 57) for Bay. The Yankees got nothing for Nady or Marte, however the Pirates might have gotten at least one more pick.
Bryce Brentz is a corner OF with power. Brandon Workman is RH SP with a fastball in the 90-95 mph range with plus movement, average curve, and good control. These are both college players. The Bucs might have picked other players, but probably of the same quality. Brentz cost $892K to sign and Workman got $800K for a total of $1.68M. Add this to the $18M they did not pay Bay, Nady, and Marte for a total of ~$20M saved.
My summary? Winning a few more games in 2008 and 2009 would have meant nothing and it would have cost us $18M. Instead of two draft picks costing us $1.8M, we have a starting LF and two SP. I’d say having $20M in the bank and 3 players at the ML level was a good deal. Maybe you could make a case that the $20M was used to sign Alverez, Sanchez, Tallon, and Allie, etc.
I'd give Neal a thumbs up for these deals.