The Oilers have so many issues - but most stem from Kevin Lowe and Darrell Katz.
Despite all of their high first round picks, the Oilers have drafted really poorly. Since 2010 - Martin Marancin in the only 2nd round pick to have developed into anything. Actually, you could go back to 2007 because they traded away their 2nd round picks in 2007 and 2008, and drafted Anton Lander in 2009. Tyler Benson is developing well, but not in the NHL yet. But that's not a lot of returns from over a decade of 2nd round picks. Over the same period - Anton Slepyshev and Jujhar Khaira are the only 3rd round picks to have developed - but again, they traded away a lot of picks as well.
In the first round, they almost always pick the BPA - Gagner, Plante, Nash, Eberle, Paajarvi-Svensson, Hall, Nugent-Hopkins, Klefbom, Yakupov, Nurse, Draisaitl, McDavid, Puljujarvi, Yakamoto. But only Nurse and Klefbom on defense. Even in 2012 when they picked Yakupov 1st overall, they waited until their 5th pick (4th round) to select a defenseman - in a draft that was loaded with D. You would think at that point, with some mixed opinions on Yakupov even at the time, they might have traded down to select one of Ryan Murray, Griffin Reinhart (whom they later traded for, and then exposed to expansion), Morgan Rielly, Hampus Lindholm, Mathew Dumba, Derrick Pouliot, Jacob Trouba or Slater Koekkoek who were all picked in the top 10. To be sure, Reinhart and Koekkoek have not panned out and Pouliot is a work in progress still, but how would Trouba or Rielly look on the Oilers blue line?
They have also rebuilt 4 times in the last decade plus.
The first was following the Pronger trade when they jettisoned Pronger (forced), Spacek, Peca, Samsonov, Smyth and drafted or acquired Sam Gagner, Andrew Cogliano, Robert Nilsson, Tom Gilbert, Dustin Penner, Sheldon Souray, Mike Comrie, Mathieu Garon and Dwayne Rolosen. They also drafted Paajarvi-Svensson and Eberle after climbing briefly out of the cellar, but this turned into just a dead cat bounce.
So they reset again. Kevin Lowe kicked himself upstairs and hired Tambellini who shipped out Mathieu Garon, Sheldon Souray, Steve Staios, Dustin Penner, Andrew Cogliano, Tim Gilbert, Eric Cole and Kyle Brodziak and brought in Patrick O'Sullivan, Ales Kotalik, Ryan Whitney, Colten Teubert, Ryan Smyth (again) and Nick Schultz - and drafted Taylor Hall, Tyler Pitlick, Marty Marancin, Ryan Nugent-Hopkins, Oscar Klefbom, David Musil and Nail Yakupov. They also hired Pat Quinn and Tom Renney, and the Ralph Krueger, then Dallas Eakins. This time they didn't even get the dead cat bounce.
So they Lowe fired Tambellini, and hired Craig McTavish and rebuilt again - shipping out Ales Hemsky, Shawn Horcoff, Paajarvi-Svensson, Devan Dubnyk, Sam Gagner, David Perron, Jeff Petry, Ben Eager, Ryan Jones and Tobias Rieder - bringing in Darnell Nurse, Anton Slepyshev, Denis Grebeshkov, David Perron, Ilya Bryzgalov, Leon Draisaitl, Benoit Pouliot, Mark Fayne, Nikita Nikitin, Teddy Purcell, Matt Hendricks, Ben Scrivens etc. etc. Again - not even an up tick in performances, so ...
Do we call the Chiarelli era a seperate rebuild or a continuation the the McTavish teardown? Out went Boyd Gordon, Keith Aulie, Martin Marincin, Derek Roy, Viktor Fasth, Taylor Hall, Nail Yakupov, Ben Scrivens, Justin Schultz, Teddy Purcell, Benoit Pouliot, Jordan Eberle, Brandon Davidson, Griffin Reinhart (in and out), Tyler Pitlick, David Desharnais (in and out again), Anders Nilsson (in and out again) Matt Hendricks and in came Connor McDavid, Andrej Sekera, Cam Talbot, Mark Letestu, Eric Gryba, Adam Larsson, Patrick Maroon, Matt Benning, Kris Russell, Zack Kassian, Jesse Puljujarvi, Drake Caggiula, Milan Lucic, Ryan Strome, Kailer Yamamoto and Jussi Jokinen Mike Cammellari.
They aslso developed poorly. In an article in yesterdays Edmonton Journal, Elliott Friedman wrote a piece that basically tees off on the Oilers player development - highlighting the mishandling of prospects both in the NHL and in their AHL team, Bakersfield. Apparently they tend to favour veterans with prime (PP) ice time over prospects like Caleb Jones, Ethan Bear and Ryan Mantha, Jordan Oesterle and Joey LaLeggia. Others have been rushed to the NHL prematurely and lost confidence. He listed the many failed prospects including David Musil, Travis Ewanyk, Curtis Hamilton, Colton Teubert, Mitch Moroz Marco Roy, Bogdan Yakimov, Ryan Martindale, etc.
Now where are they? They are built very poorly with the fastest player in the world surrounded by a bunch of big slow forwards and a static, porous defense. Theuy are currently second last in the Western Conference and facing some serious salary cap decisions (likely Ryan Nugent-Hopkins) in the spring, and likely a couple of panic trades in the next few weeks. This is what happens when rebuilds fail. Not that all rebuilds fail, but in the salary cap world a rebuild has to be steep and deep. If it takes too long or has to reset midway through you risk running into salary cap issues before you become competitive.