1. Mike Milburry
(this guy destroyed the New York Islanders by himself)
Traded Zdeno Chara, Bill Muckalt & 1st Round Selection (Jason Spezza) for Alexei Yashin
It is very hard to argue that without Alexei Yashin, Michael Peca and Chris Osgood, the Islanders would have made a return to the Stanley Cup playoffs in 2001-02. However, the long-term effects of this deal are still felt by the Islanders and their fans.
Alexei Yashin went on to become the captain of the Islanders but was ultimately bought out by the organization. Zdeno Chara went on to win the Norris Trophy and Stanley Cup with the Boston Bruins while Jason Spezza turned into one of the cornerstones of the Ottawa Senators franchise. Milbury simply gave up too much potential for Yashin as soon as he was afforded some job security under Charles Wang and Sanjay Kumar.
Getting Yashin for the short-term would not have been a bad deal, but having Zdeno Chara and Jason Spezza on the same team speaks for itself.
Traded Olli Jokinen & Roberto Luongo for Mark Parrish and Oleg Kvasha
Trading Roberto Luongo and Olli Jokinen was arguably Milbury’s worst move as the Isles’ GM. Mark Parrish was not the focal point in the Luongo deal as Milbury expected great things from the enigmatic Kvasha.
Olli Jokinen wound up having great stints with the Florida Panthers and Calgary Flames and Luongo managed to make a Stanley Cup Finals appearance with the Canucks. Both players could have developed into powerful players with the Islanders, but Milbury’s dealings on June 24, 2000, will forever haunt Islanders fans.
Mark Parrish wound up being a fan favorite in Long Island and scored some key goals during his stint with the team. On the other hand, Oleg Kvasha wound up being a major bust and was among the many players that Milbury mistakenly put his trust into.
Traded Bryan McCabe, Todd Bertuzzi & 3rd Round Selection (Jarko Ruutu) for Trevor Linden
Bryan McCabe, Todd Bertuzzi and Trevor Linden have all had good careers in the NHL, but the potential that Milbury gave away in this deal make this one of his most awful transactions as the GM of the Islanders.
When the Islanders acquired Linden, many Canucks fans were upset that their team captain and fan favorite was traded to New York. However, Linden was a shell of his former self after the 1997-98 NHL season and the talent that the Islanders gave up in exchange for the center was just lopsided.
Bryan McCabe flourished in Toronto and Bertuzzi wound up having six straight seasons (1999 to 2006) of at least 50 points scored for the Canucks. Even though Linden never really worked out for the Islanders, Bertuzzi and McCabe were not given sufficient time to develop on Long Island. Some have pointed out that Bertuzzi would never have succeeded in Long Island because there was so much pressure on him, but that assumption (thanks to Mad Mike) was never allowed to fully play itself out.