Marian Hossa who was instead traded to the Pens in 2008
This one is probably closer than anything in this thread.
I discussed, at length, though quite cryptically at the time, the Hossa-to-Montreal trade and I really can't get into much more detail right now because of the requirements of this website to reveal sources for information, but I worked for a major sports network at the time of that trade deadline and I can tell you that Marian Hossa to the Montreal Canadiens was reported as being a "done deal" very late in the evening the night before the trade deadline. In the lengthy thread on the Canadiens message board I stated it was a done deal. Within a half hour of posting that, and right as I was about to leave the studio I was told that the Canadiens were trying to expand the deal to possibly include Bobby Holik and/or Johan Hedberg, which would have been a massive transaction. I said "So it's not a done deal?" and I was told, "No, it's done, it just might be a bigger transaction." I asked how big a deal it would be, and was told that Holik wouldn't cost much and it would be more about balancing salaries. Keep in mind, this was pretty late in the evening. In the morning, only really hours later, I arrived at work and was told that there was now another strong bidder and that the Montreal Hossa deal "could fall through." The other team, however, was *not* the Pittsburgh Penguins. Leading up to the deadline, Atlanta seemed to be leveraging another team to get more out of Montreal (what they were offering up wasn't a King's Ransom by any stretch. I recall Ryan O'Byrne and Mikhail Grabovski being two of the roster players in the package and Guiallame Latendresse was also bandied about, though I don't think it was ever all three of those guys, just different combinations. In terms of the larger trade, I can't fathom why any scenario would have seen Johan Hedberg involved.)
Anyway, right as it got down to the wire, one again, the Canadiens were the front runners and then with only minutes until the deadline, the Penguins made their offer and Montreal could not match the piece the Penguins were willing to dangle a piece, that, perhaps ironically, ended up being virtually worthless: Angelo Esposito.
After the fact, I was told that if Montreal hadn't tried to add in Holik, the paperwork could possibly have been signed and sent to the league the evening before and there never would have been a chance for a last minute Penguins bid. Though Don Waddell might have waited until the following day just to see if offers increased. Who knows. Interestingly, the Thrashers ended up not trading Holik at all at the deadline.