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At the 2007 trade deadline, the Edmonton Oilers traded pending unrestricted free agent Ryan Smyth to the New York Islanders in exchange for a package of prospects and a draft pick.
Four years and one day later, they made an almost identical trade involving Dustin Penner, sending him to the Los Angeles Kings for a package of draft picks and a prospect.
Penner has a year left on his deal, but Smyth in 2007 was a better player than Penner in 2011 (and Smyth in 2009 was still a better player than Penner in 2013). In a lot of ways, though, the defining difference between the trades is the difference in draft pick - the gap between Alex Plante and Oscar Klefbom.

In the Smyth trade, the players acquired fizzled. Robert Nilsson and Ryan O'Marra were both first round picks, but they were also both somewhat problematic prospects when the Oilers acquired them. 
  • Nilsson was 22 and and just below the point-per-game pace in the minors; while the numbers were decent given his age he should not have been considered a high-end prospect. He had one nice run with the Oilers in 2007-08, played two more less impressive years and found his way out of the NHL after that, with the final year of his contract bought out by Edmonton.
  • O'Marra was about to turn 20, and hovering around the point-per-game mark in junior. Injuries played a role in that, and O'Marra's resume was always more about his complete game than scoring alone, but they were troubling numbers for a first round pick at that age. He ended up in a defensive role in the minors and spent time in the ECHL; he played 31 NHL games with Edmonton before moving on. 

That isn't to say either guys were write-offs, but neither was a shining example of prospect perfection - both had issues when the Oilers acquired them.

But also coming in that trade was a first round draft pick - a 15th overall selection - in 2007. The Oilers used it on Alex Plante (though a quick glance back shows there was a mushy spot in the middle of the draft that year) and had to be disappointed when he faltered immediately the following season. He has recovered enough to play 10 NHL games but at this point is not a player of interest. Ultimately, the failure of that pick meant that the Oilers ended up with Robert Nilsson and a pair of 'tweeners as the return on what was at the time their franchise player.
In the Penner trade, instead of one pick and two prospects the Oilers got two picks and one prospect. Leaving out the first round pick for a moment, neither of the other pieces (Colten Teubert and a conditional draft choice) was particularly inspiring at the time.
  • Teubert had been a high draft choice, but at the time of the trade was two weeks shy of his 21st birthday and a middling AHL defender. The strengths on draft day were still strengths - primarily mobility and physical play - but the weaknesses (generally described as play with the puck and hockey sense) were also still weaknesses. He was in the Nilsson/O'Marra range in that while there were good things about him, he wasn't a blue-chip prospect at the time of the trade.
  • A conditional draft pick - a second round choice in 2012 if the Kings won the 2011 Stanley Cup; otherwise a third round choice. This ended up being 91st overall pick Daniil Zharkov - a middling prospect who hasn't helped his cause with a mediocre 2012-13 campaign.

The other piece of the trade was a first round draft pick - the 19th overall choice in 2011. The Oilers again used the pick on a defenceman, Oscar Klefbom, but the difference is that Klefbom (at least at this juncture) seems likely to be a player. Injuries have been a concern but at this point he's a significantly better player than Plante was at this point four years ago.

The reality is that the returns for Smyth and Penner were nearly identical. But the key draft pick - 15th overall in 2007, 19th overall in 2011 - was used differently. 'Klefbom for Penner' sounds worlds better than 'Plante for Smyth' but that's not what the trades were; really, it was 'mid-first round pick for ___' in both cases. It's one of the ways a good scouting department can make a bad trade look good, and a bad scouting department can make a good trade look bad.
 


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