I'm using 2005-current... and ignoring trades for minor league/fringe players or pick-only trades
For Ottawa ... I'd say overall their trades with USA teams in this period have been fairly been, with a few good wins (Turris, Anderson), a few good hockey trades (Methot, Lehner) and a few obvious losses (Havlat/Bishop).
Hossa/de Vries for Heatley (fair value)
Bochenski/2nd for Arnason (Ottawa loses)
Havlat/Smolinksi for Preissing/Barinka/Hennessy/2nd (Ottawa loses)
Kaigorodov for Comrie (Ottawa wins)
2nd rounder pick for (rental) Saprykin (fair)
Schaefer for Donovan (fair)
Corvo/Eaves for Commodore/Stillman (fair)
6th round pick for Marty Lapointe (fair)
Meszaros for Kuba/Picard/1st (fair)
McAmmond/1st for Campoli/Comrie (fair)
Vermette for Leclaire/2nd (fair)
Heatley trade (evenin the long run)
Picard/2nd for Cullen (fair)
2nd for Sutton (fair)
1st for Rundblad (fair)
Fisher for 1st (fair)
Kelly for 2nd (fair)
Ruutu for 6th (fair)
Elliot for Anderson (Ottawa wins)
Kovalev for 7th (fair)
Compoli for 2nd/Potulny (fair)
3rd for Filatov (justified risk - fair at the time)
Klinkhammer for 7th (fair)
Turris for Rundblad/2nd (Ottawa wins)
Bishop of 2nd (Ottawa wins)
Gilroy for Lee (everybody loses)
Foligno for Methot (win-win)
Kassian for 4th (fair)
Conacher/4th for Bishop (Ottawa gets bent over)
Ryan trade (fair)
Spezza trade (slight edge to Dallas - depending on Nick Paul)
Lehner/Legwand for 21st overall (fair)
Prince for 3rd (fair)