On March 28th 2013, Jarome Iginla was traded from the Calgary Flames to the Pittsburgh Penguins in exchange for a 1st round draft pick (likely to be at the end of the 1st round) and two American college prospects, Ben Hankowski and Ken Agostino. Before this deal was announced, news broke that Calgary had agreed to a deal with the Boston Bruins, which was by all accounts a better offer. The Bruins were willing to move Alexander Khokhlachev (a Russian who collected 193 points in 152 OHL games) and Matt Bartkowski (a defenseman who has collected 46 points in his last 106 AHL games).
Iginla had a no trade clause in his contract and he had presented a list of 3 teams to General Manager Jay Feester that he was willing to be traded to. Instead of negotiating the best deal possible with one of these three teams then taking that best offer to the player, Feester negotiated 2 deals then took both of them to Iginla, and he chose Pittsburgh. Feester failed miserably. When a player gives you a list of three teams, negotiate the best deal and take the best deal to the player. Don't also take the inferior offer and give him the option of choosing it! Granted, it is also possible that Feester took only the Boston deal to Iginla, and that he reneged on his willingness to go to Boston (changing his mind, and demanding a trade with only one team), but certainly nobody has admitted that publicly. That would reflect poorly on Jarome, especially in Calgary.
Why was the Boston offer better? First of all, both the assets Boston was offering have already signed pro contracts and are now playing in the AHL. The two college players have the option of going the Justin Schultz route, and becoming unrestricted free agents. The Russian scored at a level in Canadian Major Junior that gives him a better chance of high level NHL production than both the Penguins college players combined. Agostino has about a 15% chance of being as good as Lee Stempniak. Hankowski has roughly a 10% chance at being as good as Drew Miller or Justin Abdelkader. Odds are that neither player will ever be a regular in the NHL. There is about a 25% chance that Calgary will get one decent 3rd or 4th line player out of the two college guys.
At least the players Boston was offering are under pro contracts, with one having a higher probability of high end production. The college guys might choose to go UFA instead of signing in Calgary, and if they do, they are a longshot at being 3rd liners. Columbus at least got 3 NHL hockey players (and a 1st pick) for Rick Nash. The prospects and pick that Calgary got for Iginla might never play a game in the NHL. This was supposed to be the most important deal in franchise history, and Feester has in all likelihood screwed it up. If I were a Calgary fan, I would be furious. Add to that picking a Canadian high school player in the 1st round last year, the botched signing of Ryan O'Reilly, and Jay Feester has quickly established himself as one of the worst GMs in hockey.