If you spend time around the interweb (you're here, so you must), you've probably seen someone call the Oilers "Islanders West," or something similar. As it happens, the troubles the Isles are having has nothing to do with Edmonton, as the two teams aren't that similar at all.
Whether or not you believe the Oilers' rebuild started in 2007, the fact remains that it was then that the team first finished low enough to pick high in the draft and began to accumulate assets. We'll have a peek at both the Oilers and Islanders from 2007 onward, and note the similarities and differences. Both teams are sporting players that were drafted first overall, but there is a lot separating them as well.
Since 2007 the Oilers have made 8 selections in the top 22 spots of the Draft. The pick they surrendered in the Penner offer sheet ended up becoming Tyler Myers (oops), but at least the Oilers were able to turn Penner into one of the 8 first rounders (Klefbom), as well as former 2008 first round choice Colten Teubert. Including Teubert, they've added 9 players taken within the top 22 in five years. Five of those players (Gagner, Eberle, Paajarvi, Hall and RNH) are already in the NHL and all except Paajarvi are bona fide impact players.
By contrast, the Islanders have added 5 players who were picked in the top 12 since 2007, along with Brock Nelson who went 30th in 2010. Of those, John Tavares, Josh Bailey and Nino Niederreiter are the only ones in the NHL, and only Tavares has been truly impactful.
Wrong though it may be that failure is rewarded richly in the NHL, that is how the Draft works. Had the Islanders picked first overall in consecutive years, as the Oilers did, they would be sitting on John Tavares and Taylor Hall. Instead, the Islanders picked Nino Niederreiter 5th in 2010, who has only 2-1-3 in 48 NHL games thus far. They picked 5th last year as well and took Ryan Strome. Strome has many good characteristics, but he has taken a bit of a step back this year with the Niagara IceDogs in terms of points per game.
For whatever reason (see: luck; losing a lot), the Oilers have had the edge over the Isles at the Draft. In 2008 New York picked Bailey 9th overall with Jordan Eberle still on the board, who didn't hear his name called until 22nd. Because of horrendous losing seasons Edmonton picked up Hall before Niederreiter and Nugent-Hopkins before Strome.
But it wasn't just that. One of Edmonton's first round picks in 2007 originally belonged to the Islanders, and was traded to the Oilers in the Ryan Smyth deal. Also in that deal were the Islanders' 2003 and 2005 first round picks Robert Nilsson and Ryan O'Marra. The resulting player, Alex Plante, isn't setting the world on fire with his play, but New York never had the chance to make the right selection.
Outside the Draft, the Islanders have other problems. Say what you will about the Oilers' blue line, but the men patrolling the back end on the Island may be worse. Mark Streit is the only veteran locked into a contract beyond this year, and that's probably a good thing considering that the roster is a who's-who of badness. Milan Jurcina (minus-28), Mark Eaton (minus-12), Steve Staios (minus-13), and Dylan Reese (!?) make what the Oilers are packing look like the 2007 Anaheim Ducks.
Any other troubles? Sure!
The Islanders may lose one of their leading scorers in PA Parenteau to free agency. Also, after a monstrous 34 goal season last year, Michael Grabner has seen his production slip to 15 goals in 62 games. Rick DiPietro has played a total of 47 games over the last four seasons, and his contract (which expires in 2021!) makes Khabibulin's seem like a bargain. Evgeni Nabokov has been good as a replacement, but unless they can get him re-signed he'll be gone in the off season as well.
As you can see, it's a combination of really bad management, bad luck, and not selecting at the very top of the Draft that has made the Islanders this horrible. Their run of top-five picks actually makes them closer to the Columbus Blue Jackets than it does to the Oilers.
Make no mistake, however. Having a boatload of picks in the first round does not guarantee success for the Oilers. Having said that, the NHL Draft is a crapshoot and the more choices you have in the high-probability rounds, the better your odds of success. The Islanders haven't done as much as the Oilers have since 2007 when it comes to gathering extremely high end assets, which is why Edmonton and New York are very different. Having another pick as high as second (or even first) overall will only put the Oilers that much further ahead, and widen what will one day be a large gap between them.