8- Jocelyn Thibault, Aug 10 2005, 2 years $3M: Signed by Craig Patrick. Over 2 seasons he had 8 Wins, 17 Losses, with a 3.52 GAA and an .894 SV%. That's a waste of money, even more so in a world with a $39M salary cap.
*- James Neal, Feb 19 2012, 6 years $30M: Signed by Ray Shero. You can make an argument that this contract doesn’t belong here based on regular season production, but he also played in the playoffs with a healthy Crosby and Malkin twice under this contract and never won a Cup (including 4 PTS in 13 GP in 2014). That’s a fail.