#2 Michael Nylander
Michael Nylander signed with the Capitals on July 2, 2007 for four years and $19.5 million. It was actually his second stint with the Caps having been a member of the team back in the 2002-03 season when he was traded by the Chicago Blackhawks. Nylander got traded a year later to the Boston Bruins during the team’s fire sale.
Nylander had 17 goals and 39 assists for 56 points in 71 games the remainder of that 2002-03 season. The next year he had two assists in three games before being dealt to the Bruins. He came back to the Caps in 2007 as a 35 year old looking to help lead one of the younger teams in the league. Yes believe it or not the Caps were actually young at one point in time.
Nylander had 11 goals and 26 assists for 37 points in 2007-08 and followed that up with nine goals and 24 assists for 33 points the next year. When Nylander joined the Caps in 2007, he backed out of a deal with the Edmonton Oilers which pissed them off. He signed a four year contract with Washington.
Nylander had previously posted career highs of 26 goals and 57 assists with the New York Rangers. Nylander’s first season with the Caps was cut short with a shoulder injury. In his second season, his role declined and his playing style clashed with Bruce Boudreau’s coaching style.
Nylander had a $4.9 million cap hit and a no movement clause which made it impossible to deal him. He was even banished from the practice facility by November 2009 and then loaned to Grand Rapids of the AHL. He would later finish that season in Finland. He never played another NHL game.