People keep suggesting that the Rangers passed on Giroux for Sanguinetti, as if the Rangers had considered Giroux. But, from what I remember, (which included some of our HF sources at the time, i.e., and Edge and SOTI), the Rangers were set to take Berglund, until Sanguinetti fell to them. Giroux was not going to be the pick, so I don't see it as having been an option.
How about becoming obsessed with Montoya's performance, and passing up the chance to trade up to get Andrew Ladd. And, then trading up later, only to take Korpikoski, and not Zajac. Or missing out on David Booth, (a name that was being discussed on these boards at the time), and taking Darin Olver and Dane Byers instead. Or passing on Nashville's offer of two 2nd round picks for Petr Nedved, only to do a favor for Sather's old franchise in Edmonton, by accepting a lesser package?
The three that always bother are the three deals with the Blues that fell through -
1992 - Adam Oates was on the block, and Smith was offered Oates and Jeff Brown, and another lesser piece for Nemchinov and Patrick, and another lesser piece. Smith went to Roger Nielsen, who said don't make the deal. Think having Oates as the 2nd line center might have made a difference in the playoffs that year?
1995 - Smith and Keenan, (GM/coach at the time) had a deal in place for Shanahan to become a Ranger, for the price of Kovalev and Matteau. But, Smith needed ownership approval during a time when the Rangers and Knicks were being sold. Keenan got impatient, and made the deal with Hartford, for Chris Pronger instead.
2001 - Sather was set to send Mike Richter to the Blues for a package of prospects, which I believe included both Barrett Jackman and Michal Handzus. Handzus was going to be spun with Lundmark and Theo Fleury to Phoenix for KT. The deal was just about final, but, Ron Low decided to play Richter against Chicago, (I believe), and that was the game where Richter broke his skull. Needless to say, the deal was off.