Scuderi. Handzus. Stuart was a good give him a shot signing. Penner made sense. I still get the theory behind Lucic, so I have to throw that in.
I'd say Vis/Still/Greene, but that was also completely based on having Doughty. Solid move though.
Just because luck is involved doesn't mean DL didn't have to take the risk. If Williams isn't hurt for a number of years in a row, he's probably not available, but DL took the risk. Mitchell, had to give an aging guy with a concussion and extra year, but it worked. Richards and Carter were luck, but you also can't force teams to get rid of those kinds of players. The other team has to want to get rid of them, or the player has to want out, otherwise you're not getting them.
Smyth would be another good move. You almost have to get him, just because the price was do low. It's not like he had 12 goals here the way Penner did. Smyth was actually productive.
DL was good at buying low. Couldn't sell high worth a damn, but enough of the numerous reclamation projects worked out that he was able to piece together a team dripping with moxy. Up to and including the eventual Cup winning coach.