Basically, name some trades, signings or general team moves (management, roster, etc.) that were deemed very risky at the time, but paid off.
In recent memory, the Habs handling of Price/Halak comes to mind. Price had a great rookie year, took a big step down in his sophomore year, and was outplayed by Halak in his third year. Halak came off a spectacular post-season and looked to be a real keeper, then he was traded away for Lars Eller and Ian Schultz. Since then Price has been great, putting up a Vezina-calibre season in 2011 and having a good season behind a pretty bad team this past year.
It still remains to be seen who ends up having the better career, but I would bet on Price at this point. Halak has played well but I don't know if he can handle full starting duties, he seems best when playing in a tandem. Also, despite being 2 years older Price has played 71 more games than him in their careers. Of course, some of that is due to injury, but still.
The Panthers as a team have been one giant roll of the dice since Tallon took over. Signing a bunch of players to contracts most teams would have no business with, but getting pretty good success out of them in the end, including a playoff birth that the franchise badly needed.
Kessel to the Leafs, although most expected that the Leafs were a team that would struggle and the Bruins would snag a reasonably decent pick, nobody could have anticipated that the Leafs struggles would have led to a 2nd pick (Seguin), then the 32nd pick(Knight, jury still out) and then Hamilton the next season in the 9th spot.
Risky getting rid of a 30+ goal man in Kessel but so far, already happy if the end result is only getting Seguin but................Hamilton will be a very significant NHL`er sooner than later and Knight could play a big role as a very solid 3rd line depth guy, max 2nd liner
Kari Lehtonen for Dallas. The Stars traded away their #1 prospect, and only PMD in the system in Ivan Vishnevsky for an oft injured starter. Ivan couldn't crack 2 team's rosters and bolted to the KHL, and the Kari is the Stars starter for the next 4-5 years.
I guess there is a few small undrafted players that could be included. St.Louis being one of the most notable, Tampa Bay gambled on him after Calgary bought him out when he wasn't selected in the expansion draft.
Toronto trading for Joffrey Lupul from Anaheim. I heard the player Brian Burke really wanted was Jake Gardiner and Bob Murrary said to have him they needed to take on Lupul's contract since he was coming off back surgey and an infection after that, which basically meant there wasn't any room for him with the Ducks. Thankfully this trade has paid off because Lupul plays great on the same line with Phil Kessel and Jake Gardiner had a fantastic rookie season which was a surprise because we didn't see him making the team out of training camp.
Dallas gambled trading away a young Iginla for Nieuwendyk. Gamble paid off big time, not only did they win a cup with Nieuwendyk but he's currently their GM.
Came to post this. It was a gamble for both teams, and both teams got the best possible return. A rental that goes on to win the Conn Smyte on route to a Stanley Cup, traded for a prospect who ends up being the best player in franchise history. I think this is my 'favorite' trade in sports history just because it worked out so perfectly for both teams.
My contribution - $1 for Kris Draper. That $1 could have been used somewhere else, it could've been the difference between getting a superstar free agent and not getting one, but Detroit took the gamble anyways. And Draper ended up being a Selke winner and an important part of several Cup wining teams.
Blues trading stud D prospect in David Rundblad for the 16th pick. That pick became Tarasenko. Risky cause he could choose to stay in Russia. He has signed and looks like a home run selection. Thanks Jarmo!