The Chicago Blackhawks were missing those last few depth players in 2014 I guess. So they sent their second-round pick to the then Phoenix Coyotes for David Rundblad and Mathieu Brisebois. Rundblad did play for the Blackhawks but Brisebois was nothing more than an AHL player.
The second-round pick the team traded away turned into Christian Dvorak who is 25 and just put up 31 points this past season. Players like Dvorak are what the team is missing now, but alas this team needed Rundblad and Brisebois at that time. Hindsight is always 20/20
And a first-round pick is on the table everybody. The 2015 season was the first time the Blackhawks would buy in at the deadline and give up their first-round pick in the Stan Bowman era.
The team sent their first-round pick and Klas Dahlbeck packing to the Coyotes for Antoine Vermette in return, and the rest is history. The team also picked up Andrew Desjardins for the San Jose Sharks for Ben Smith and a seventh-round pick. And worst of all the team sent two second-round picks to the Philadelphia Flyers for Kimmo Timonen. Wade Allison, one of the two second-round picks played his first 14 games in the NHL this past season.
The Blackhawks did end up winning the Stanley Cup that season, but giving up two second-round picks for Kimmo Timonen seems extreme.