#3 Jaromir Jagr and Frantisek Kucera for Kris Beech, Michal Sivek, and Ross Lupaschuk
The trade for Jaromir Jagr in the summer of 2001 was the first big move of the Ted Leonsis ownership era but this era simply did not work out. Prior to landing in Washington, Jagr was excellent with the Pittsburgh Penguins but the change of scenery from the Steel City to the Nation's Capital did not materalize the way loyal Caps fans envisioned.
Jagr made nine NHL All Star Games and won back to back Stanley Cups with the Penguins in 1991 and 1992. Trading for him before that 2001-02 season brought on a lot of hype around the area with fans thinking the Caps would turn the corner and hoist the Stanley Cup soon in those early 2000s.
What was even worse was after the trade the Caps decided to sign him to a lucrative seven year contract worth $77 million before he even suited up for a single game with the Capitals. The Caps in return sent three of their prospects in Kris Beech, Michal Sivek, and Ross Lupaschuk.
Jagr averaged 40 goals per season during his time with the Penguins but that number dipped to an average of 28 goals in the three seasons he played with the Caps.