6. Alexei Yashin to the New York Islanders (2001)
On the surface, Alexei Yashin looked to be Ottawa’s brightest star. Drafted 2nd overall in 1992, Yashin immediately impressed and after a blistering 94 point season 1998-99 he was Hart Trophy runner up. Off the ice though, his relationship with both Senators management and fans alike was poisonous. Problems arose in 1993 when 1st overall pick Alexandre Daigle was given a larger contract. Yashin was incensed and this began a trend of bitter contract disputes.
During the 1995-96 season, Yashin held out and demanded a renegotiation of his deal. While the desired franchise cornerstone Daigle struggled, Yashin thrived but the holdout was met with criticism by both Senators fans the media. The Russian refused to play at all during the 1999-00 season again due to his contract dispute and the Sens stripped him of the captaincy and suspended him indefinitely. Upon his return the next season he was loudly booed by both Ottawa and opposing fans.
Initially reluctant to move on their star, Ottawa finally caved during the 2001 NHL Draft. Yashin was traded to the New York Islanders in exchange for Zdeno Chara, Bill Muckalt and a 2nd overall pick (which was used to select Jason Spezza). Isles GM Mike Milbury then took the impulsive decision to sign Yashin to a massive 10-year deal worth 87.5 million. During his 5 stop-start years in Long Island Yashin’s production declined considerably but he was virtually untradeable due to poor form and his gargantuan contract. He was bought out by the Isles in 2007. A talented player whose demands overshadowed his potential.