Ryan Smyth, Edmonton Oilers
First time Oiler from: 1995-96 to 2007-07
Left via: Trade deadline deal to the New York Islanders, made a tearful departure after failing to reach an extension and a minimal separation of a couple hundred thousand dollars.
After Edmonton: He finished the 06-07 season with the Islanders, then signed with the Avalanche. Two years with the Avs followed by a pair in LA with the Kings and then he was dealt back to where he never should have left in the summer of 2011.
Dustin Penner, Anaheim Ducks
First time Duck from: 2005-06 to 2006-07
Left via: After winning a Cup with the Ducks in 2007, Penner was Bryan Bickell before Bryan Bickell existed, and he used a strong playoff run to garner an offer sheet from the Edmonton Oilers for 5 years and over $21M. That contract was considered vastly overpaying and Brian Burke publicly chastised the Oilers and got into a verbal sparring match with Kevin Lowe over offering a player with just over 100 NHL games such a lucrative deal.
After Anaheim: After failing to live up to the contract for 4 unspectacular seasons in Edmonton, he was traded to the Kings, where he continued to flounder with LA, until he had a solid playoff run during the Kings Stanley Cup win in 2012. He signed back in Anaheim as a free agent for the 2013-14 season.