March Sadness: Which Oilers Season Was The Worst -- (#3) 2009/10 vs (#6) 2006/07

We've now know our first member of the March Sadness Final Four, thanks to a decisive win by the fourth seeded 2013/14 season over the current team. With 2013/14 getting a whopping 91% of the vote, it's probably a safe bet to assume that the optimism that surrounds Connor McDavid at all times was a big factor in the minds of many voters.

Today we get what is easily the most intriguing match-up of the Elite Eight, with the season that trigger the Oilers' great, never ending rebuild taking on the team's original death march. This should be a real battle.

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#3 -- 2009-10 - 62 points (27-47-8)

Finish: 30th
Goal Differential: -70 (30th)
Power Play: 5.62 (22nd)
Penalty Kill: 7.30 (26th)

Steve Tambellini had big plans for the Oilers in 2009/10. He had a new man behind the bench in Pat Quinn. He'd signed a new number one goalie, and former Stanley Cup winner, Nikolai Khabibulin to a four-year deal worth $15M to replace Dwayne Roloson. Sure he came up short trying to land Dany Heatley in a deal that would have sent Andrew Cogliano, Dustin Penner, and Ladislav Smid to Ottawa, but that was just one piece. The Oilers were spending to the cap and this was the season that things were really going to turn around for the franchise.

Things were ugly right from game one for this Oilers team, starting with Khabibulin handing the Flames the game winning goal on opening night. With something like that you're tempted to think that things can only improve from here, that they can't possibly get worse. And if this is what you thought after watching that game, you were very, very wrong. Things did not get better for the Oilers, in fact they got a whole lot worse as a team that wasn't very good to begin with was even further depleted by injury. The losses mounted and by January the word rebuild was being tossed around for the first time that I can recall.

And rebuild is the route that the Oilers took, trading Denis Grebeshkov to Nashville for a draft pick, Lubomir Visnovksy to Anaheim for Ryan Whitney and a draft  pick, and Steve Staios to Calgary for Aaron Johnson and a draft pick; in hindsight it might have been wise to cut just a little bit deeped in that first rebuilding season. The rebuilding Oilers rode that wave of suck all the way to a 62 point, 30th place finish, not quite the lowest point total in franchise history but close. At the lottery the Oilers won something for just about the first time all season, and then used that first overall draft pick to select Taylor Hall, who would be the cornerstone of the team's rebuild.

#6 -- 2006-07 - 71 points (32-43-7)

Finish: 25th
Goal Differential: -53 (25th)
Power Play: 14.2% (27th)
Penalty Kill: 84.5% (8th)

The Oilers had just come off an improbable, magical, run to Game 7 of the Stanley Cup Finals. Sure, Chris Pronger was gone, having asked for a trade almost before the Hurricanes parade had ended, but the Oilers had gotten back Joffrey Lupul and Ladislav Smid and three draft picks in the deal. With five pieces like that the team was going to be able to handle the loss reasonably well. Add in the newly acquired Jan Hejda, Petr Sykora, and Daniel Tjarnqvist and you could convince yourself that things would be okay. A 6-2-0 preseason followed by a 7-4-0 record in October and there was no convincing necessary, this team was for real.

It was a pace that the Oilers would be unable to maintain though, and as the team lost more games than they won they slowly slid down the Western Conference standings. At the trade deadline the Oilers found themselves in ninth place in the Western Conference, but nine points back of eighth place Calgary. With their playoff hopes sitting somewhere between slim and none the Oilers were forced to make a decision regarding soon to be UFA Ryan Smyth at the deadline: sign, trade, or possibly lose him for nothing on July 1. In the end the Oilers and Smyth couldn't agree on a contract number and Smyth was dealt to the Islanders for Robert Nilsson, Ryan O'Marra, and a first round draft pick.

And then the wheels really came off. The same day that Smyth was traded the Oilers hosted the Coyotes. It was also Mark Messier jersey retirement night and the Oilers celebrated the occasion by losing 3-0. In the 18 games that followed before the Oilers' season mercifully came to an end, the team would win just two games and would manage to lose one more in overtime. The Oilers record after the trade deadline was a dismal 2-16-1 and the team was outscored 23 to 66. That's a -43 goal differential in 19 games, that's the equivalent of -186 over a full season. This would steer the Oilers to a 25th place finish, setting them up to draft Sam Gagner, who would be the cornerstone of the team's retooling effort.