Ray Shero, General Manager of the Pittsburgh Penguins, signed a five-year contract extension with the team Monday morning.
This should be a surprise to none as Shero has been the architect behind the Pens, shaping together a winning team that found the ultimate success by winning the Stanley Cup in 2009.
Despite the incredible success Shero has seen in his four years, it hasn't been all smooth sailing for him and the team. There have been times when fans have placed their trust in Shero and the potential of a player, only for everything to come up empty.
These gaffes have made their mark on the team and the unfortunate redistribution of players. Lucky for us, they have been neither frequent nor serious. It's also noteworthy to mention that Shero has managed to right some of his mistakes.
In honor of Shero's contract extension, here are his five worst moves since his start with the Pens. I am including draft picks as well as trades.