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2002: Maxime Oullet, first-, second-, third-round picks in 2002 draft to Washington for Adam Oates
Oates had scored over 1,000 points in his career at the time of the trade. He led the NHL in assists by the end of the season, but was a rental player for the Flyers.
He was meant to help the team's offense in a playoff run, but Philadelphia scored just two goals in a first-round exit to the Ottawa Senators
It should be noted that Oates assisted on both goals, but it was not worth giving up their top goalie prospect and their first three picks of the draft.
Oates was signed by Anaheim as a free agent that offseason.
Also, in 1989 the team gave up two first-round picks for goalie Ken Wregget.