Brought this one up in a similar thread, but this is probably my favorite "almost" deal that I only learned about in recent years.
The urban legend was that Quebec offered the farm for Alexandre Daigle at the 1993 Draft. They were interested but Ottawa didn't want to trade out, so both sides said that names were never discussed.
Instead Quebec's real target was Chris Pronger at #2. Quebec had so many young forwards, so a cornerstone D like Pronger would have been a perfect fit.
San Jose had #2 and their room was split. Their OHL scouts wanted Pronger, their NCAA scouts wanted Paul Kariya, but co-GM Chuck Grillo wanted Viktor Kozlov. Grillo eventually got his way and it was up to the other co-GM Dean Lombardi to trade down and get Kozlov while adding some assets.
Seemingly three teams were most interested: Quebec, Hartford, and the Rangers. Hartford had the most straightforward offer as Kozlov would probably be there with their first at #6. New York's first pick (#8) was a little too late to guarantee Kozlov. Quebec offered something centered around Mike Ricci and #10. Quebec also dangled that to Tampa for #3 and possibly would have swapped spots with San Jose, but Tampa declined.
Quebec and San Jose were going to meet the night before the draft to try to hammer something out, but Quebec's brass no showed. Lombardi was also upset that Quebec owner Marcel Aubut tried to go over his head and negotiate the deal with the Sharks owner. We were only a year removed from Quebec trading Eric Lindros twice, so they probably didn't have the best reputation around the league.
The interesting "what if" part was that Quebec offered an unsigned Peter Forsberg to San Jose straight up for the pick on the draft floor. After the draft, Lombardi fumed to the press about Quebec's chaotic negotiations. He implied he would have done the deal contingent on signing Forsberg. But since Quebec made a last minute offer, that left San Jose with no time to negotiate with Forsberg's agent.
In that CBA, offer sheets were permitted for unsigned European draft picks (after a certain amount of time). In the summer of 1992, Calgary signed Teemu Selanne to a 3 year offer sheet at 400K/season plus a 1.5 million dollar signing bonus. Winnipeg begrudgingly matched since they would have received no compensation if they hadn't. Forsberg and Markus Naslund were set to get offer sheet privileges a week after the 1993 Draft. There were rumors that Forsberg could command a 4-5 million dollar signing bonus / Forsberg was looking for something in the neighborhood of Daigle's huge contract.
San Jose wasn't sure if they could afford that, so they went with Hartford's offer instead. But it's fun to think that a Chris Pronger for Peter Forsberg trade was on the table.