Sometimes at the NHL Draft, teams will trade two or more lower picks to move up and get their guy. Other times, teams are simply looking to trade down to add more picks. Here are the 12 worst examples of draft pick trades that happened on Draft day (2006-2016). These are only trades that were draft picks for draft picks (two or more lower picks for a higher pick), no player for pick transactions. Some of these trades included picks from future drafts, so not all of them were drafted on the day they were traded.
1) 2008 Nashville: Trades #15 (Erik Karlsson) to Ottawa for #18 (Chet Pickard) and #70 (Taylor Beck). David Poile probably thought he was getting great value adding a 3rd round pick to move down 3 spots in the first round. If he had to do it over again, he probably would have drafted the future Norris winner instead of Chet Pickard.
2) 2008 Phoenix: Trades #38 (Roman Josi) to Nashville for #46 (Colby Roback) #76 (Matt Brodeur). The day after trading down from the Erik Karlsson pick, the Preds turned around and traded two picks to move up in the 2nd round to take Roman Josi, who has developed into a great defenseman himself. It's a bit remarkable that these two extremes of good and bad draft day trades involved the same team at the same draft.
3) 2006 Islanders: Trades #71 (Brad Marchand) to Boston for #98 (James Delroy) and #126 (Shane Sims). In most years draft pick value really starts to level out somewhere in the 3rd round depending on the depth of that year's draft class. Acquiring a 4th and a 5th for a 3rd is not a bad gamble, unless the other team hits a home run in that slot.
4) 2007 St. Louis: Trades #9 (Logan Couture) to San Jose for #13 (Lars Eller), #44 (Aaron Palushaj) and #87 (Ian Schultz). Lars Eller would go on to be a decent 3rd line NHLer with 213 career PTS and counting. But Couture has 424 and that gap isn't going to get any smaller going forward.
5) 2011 Toronto: Trades #30 (Rickard Rakell) and #39 (John Gibson) to Anaheim for #22 (Tyler Biggs). The fact that Biggs was a big strikeout and the Ducks hit a pair of home runs does make this trade look worse now than people probably thought on draft day. The difference in Expected Value between the 22nd pick and the 30th is much smaller than the EV of the 39th, so the Ducks should have been expected to come out ahead, just not to this degree.
6) 2008 LA: Trades #12 (Tyler Myers) to Buffalo for #13 (Colten Teubert) and #74 (Ryan House). Perhaps the worst part of this trade is that both teams passed on Erik Karlsson. The Kings would go on to win 2 Stanley Cups without Tyler Myers, but I'm sure if they could do it over again, they'd rather him than Teubert, who was a complete bust.
7) 2009 Islanders: Trade #16 (Nick Leddy), #77 (Matt Hackett), and #181 (Erik Haula) to Minnesota for #12 (Calvin De Haan). The Islanders got a future NHL player in this trade, but certainly a level or two below Leddy. The fact that Minnesota hit a home run on the 7th round pick does make this trade look worse than it would on draft day. But still, I would generally not recommend trading a 3rd and a 7th to move up 4 spots.
8) 2013 San Jose: Trades #20 (Anthony Mantha) and #58 (Tyler Bertuzzi) to Detroit for #18 (Mirco Mueller). The Sharks did get a player who is currently playing in the NHL, but not at the level where trading a 2nd round pick to move up 2 spots makes sense. Keep the 2nd round pick, draft at 20. Holland did great in this trade, getting two players who are currently in his line-up.
9) 2010 Chicago: Trades #30 (Brock Nelson) to the Islanders for #35 (Ludvig Rensfeldt) and #58 (Kent Simpson). The difference between the 30th and 35th picks is generally less than the value of the 58th pick. That was not the case here, with the Islanders hitting a home run at the 30th slot.
10) 2014 Minnesota: Trades #79 (Brayden Point) to Tampa for #80 (Louis Belpido) and #204 (Jack Sadek). This trade is only bad because Tampa hit a home run on the 3rd round pick, otherwise it was a reasonable exchange of value. I have to assume this trade took place moments before the pick with Tampa specifically targeting Point. Otherwise why trade up one slot in the 3rd round? Did anyone at the Wild draft table say "hey why don't we draft Brayden Point?"