I was going to post this as a fanshot but figured this could take a lot of directions in terms of discussion. Real Clear Sports posted the Best and Worst MLB Free Agent signings of all time. It takes a look at the ten best and ten worst free agent signings since MLB put free agency in place. It also has a number of honorable and dishonorable mentions.
In light of this article I figured we could not only add to this list but perhaps come up with the best and worst Cubs free agent signings. I know that some of this will correspond with the "can of worms" that Al's posting but this might be a fun rehash of a lot of good and bad Cubs transactions.