Edmonton Oilers: 8 Moves That Helped Send the Team to the Bottom of the NHL

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In 2006, The Edmonton Oilers came within one game of winning the franchise's sixth Stanley Cup. Five years later in 2011, they are the worst team in the NHL for the second straight year.

How does a professional sports team fall so far so fast?

Some may argue that winning the Clarence Campbell trophy made the 2006 team seem much better than they really were. Others could make the claim that the large number of injuries and man-games lost has forced the team to the bottom. While both of these statements hold some truth, the reality is that in the years leading up to and following the Oilers' 2006 Stanley Cup run, Edmonton management made some disastrous decisions that sent the team to where they are today.

Here are eight moves that helped make the Oilers the worst team in the NHL.

8. The Dustin Penner Offer Sheet

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In the NHL, submitting an offer sheet to a restricted free agent is the equivalent of asking your friend's girlfriend on a date while they are on a break. Regardless of what she says, there will be repercussions and it's generally a bad idea.

In 2007, the Oilers tried the offer sheet approach twice. First, Kevin Lowe tried to obtain Thomas Vanek of the Buffalo Sabres. When that failed, Lowe made an offer for Dustin Penner of the Anaheim Ducks. With Penner signing, the Oilers became the first NHL team in 10 years to acquire a player through an offer sheet.

While playing with Edmonton, Penner's numbers never really improved over those of his last season in Anaheim, with the exception of one breakout season in 2009-2010 where he led the team in goals and points. For a player who averaged about 45 points a season, the Oilers paid $4.25 million a year and gave up three 2008 draft picks. Those picks would eventually be used to select Tyler Myers and two prospects whose NHL value has yet to be seen.The offer sheets also alienated Kevin Lowe from several other NHL general managers, mainly then-Ducks GM Brian Burke.

In 2011, Oilers general manager Steve Tambellini traded Penner to the Los Angeles Kings for Colten Teubert (strangely enough, the player selected just after Tyler Myers), a 2011 first-round pick and a 2012 third-round pick. Arguably, the Penner offer sheet didn't hurt the Oilers in the long run, as they were able to get back pretty much what they gave up for him. But it will remain as one of the many question marks on Kevin Lowe's record as general manager.

7. The Dany Heatley Trade That Never Happened

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In June 2009, news broke of a trade between the Edmonton Oilers and the Ottawa Senators. Disgruntled winger Dany Heatley was coming to Edmonton.

The news was a bit premature, as Heatley exercised his no-trade clause and killed the deal. Rather than moving on and focusing on what was a pretty big free agent season, Edmonton general manager Steve Tambellini and vice president of hockey operations Kevin Lowe spent the next few months begging Heatley to reconsider, working through Heatley's agent and even making visits to Heatley's home. In the end, Heatley accepted a trade to the San Jose Sharks in September.

Not knowing whether or not he would have an all-star forward, and his $7.5 million cap hit by the start of the season, probably made retooling the roster that offseason pretty difficult for Tambellini. The Oilers only signed three prospects while continuing to pursue Heatley. Dean Arsene, Matt Nickerson and Chris Minard played a combined 18 games with Edmonton. Once the Heatley saga was officially over, Edmonton signed one free agent: Mike Comrie.

6. The Chris Pronger Trade

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Following the disappointment of losing the Stanley Cup Finals in 2006, Oilers GM Kevin Lowe received more bad news. Chris Pronger, one of the heroes of the playoffs, requested a trade out of Edmonton.

To Lowe's credit, any time news leaks that a player is requesting a trade out of an organization, it becomes difficult to obtain fair value for that player. On July 3rd, 2006, Lowe traded Pronger to the Anaheim Ducks. In return, the Oilers received a 2007 first-round pick, a 2008 second-round pick, a conditional pick, Joffrey Lupul and Ladislav Smid.

Lupul managed a disappointing 28 points in his only season with Edmonton. Oilers traded away both the first and second picks for basically nothing (Allan Rourke and Riley Nash). Smid remains with the Oilers and, though he could be one of the better players on the Oilers blue line, he will never be Chris Pronger.

The one saving grace for the trade turned out to be the conditional pick. Because Anaheim reached the finals during Pronger's first year, the Oilers received a 2008 first-round pick, which they used to select the very promising Jordan Eberle.

5. Tom Gilbert's Contract Extension

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Perhaps he was still kicking himself for not being able to re-sign Ryan Smyth in the year before, but in the 2008 offseason, Kevin Lowe was feeling generous with contract extensions.

There are two in particular that, at the time, seemed to most fans to be somewhat of an overpayment. Three years later, they seem to be gross over-payments.

Tom Gilbert played his first full season with the Oilers during the 2007-2008 campaign. Gilbert's 13 goals that season showed enough potential for Lowe to lock him down with a six year, $24 million contract.

Gilbert's goal production hasn't broken the double digits since. He has a career plus/minus of 25. He is one of the softest defensemen in the league and a turnover machine. On the powerplay, Gilbert doesn't fair much better. On one of the worst powerplay teams in 2011, he ranked second amongst Edmonton's defensemen with 10 points.

4. Edmonton Signs and Waives Sheldon Souray

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After a career season in Montreal in 2007, Sheldon Souray signed a five-year, $27 million contract with the Oilers. Although injuries limited his first season in Edmonton to only 26 games, he bounced back in the 2008-2009 season and posted 53 points in 81 games. Unable to stay healthy, he was again sidelined for most of the 2009-2010 season, playing in only 37 games.

The situation became toxic in the 2010 offseason, when Souray requested a trade out of Edmonton. Perhaps it was the Oilers' refusal to repeat the Chris Pronger situation and receive less than their perceived fair value for Souray, or maybe it was the question of Souray's health, but the Oilers were not able to move Souray. A public feud followed, in which Souray accused Edmonton's management of mistreating him and forcing him to play while injured. He added salt to the wound by referencing Pronger's request to leave Edmonton a few years earlier as proof of the mismanagement in Edmonton.

Oilers general manager Steve Tambellini retaliated by not allowing Souray into training camp at the beginning of the 2010-2011 season. Rather, he "loaned" Souray to the Washington Capitals' AHL affiliate, the Hersey Bears, for the entire season. The saga came to an end in the 2011 offseason when the Oilers bought out the remainder of Souray's contract.

Besides the financial loss in Souray, the whole incident added more distractions for Tambellini who probably wasted more time trying to move Souray than making other necessary moves. And for a team that has enough trouble trying to acquire free agents, the Oilers could have done without the negative publicity.  

3. Edmonton Drafts Marc-Antoine Pouliot in 2003

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The 2003 NHL entry draft is considered to be one of the best drafts of all time.

The Oilers originally possessed the 17th overall pick, but traded it to New Jersey for the 22nd and 68th overall—not a bad move in a draft as deep as 2003 was. With the 22nd overall pick, the Oilers selected from the QMJHL center Marc Antoine Pouliot.

Everyone knows that the entry draft is a gamble and sometimes even first-round picks fail to deliver at the professional level. In 179 NHL games, Pouliot has only scored 21 goals and totaled 53 points. His best point season came in 2008-2009 when he totaled 20 points.The Oilers decided not to re-sign Pouliot in 2010.

Pouliot can't be blamed for the tanking of the Oilers in recent seasons. But to select Pouliot, the Oilers passed on several talented players, including Ryan Kesler, Mike Richards, Corey Perry, Loui Eriksson, Patrice Bergeron and Shea Weber.

2. Shawn Horcoff's Contract Extension

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There are two types of Edmonton fans: those who don't like Shawn Horcoff and those who don't like Shawn Horcoff's contract.

Shawn Horcoff had a breakout season in 2005-2006 when he posted 73 points in the regular season and 19 points in the playoffs. And, although the next two seasons saw a drop in Horcoff's production to about 50 points per season, Kevin Lowe still believed Horcoff would be a much needed first-line center for years to come. Weeks after giving Tom Gilbert a contract he didn't deserve, Lowe signed Horcoff to a six-year, $33 million contract. The contract also contains a no-trade clause, meaning Horcoff will likely retire in an Oilers uniform.

Horcoff has 401 points in 684 NHL games, giving him a point-per-game average of .586. He takes more face-offs than any other player on the team, although hasn't won more than 50 percent since the 2008-2009 season. Horcoff's contract places him in a first-line center position, when clearly he belongs on the second or third line. Horcoff's cap hit will become even more problematic at the end of the 2013 season, when the Oilers will be looking to re-sign Jordan Eberle, Magnus Paajarvi and Taylor Hall.

1. The Oilers Sign Nikolai Khabibulin as a Free Agent

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While many Oilers fans approve of the job Steve Tambellini is doing as general manager to rebuild the franchise, it is easy to forget that his first free agent signing could be the biggest reason Edmonton has found themselves at the bottom of the standings for the past two seasons.

After three disappointing seasons in Chicago, Nikolai Khabibulin ended his tenure there with a bounce-back season, posting stats similar to those of his Cup-winning season with the Tampa Bay Lighting. For Tambellini, this was enough to sign the then-36-year-old net-minder to a four-year, $15 million contract.

In the first two years of that contract, the Bulin Wall has played in a total of 65 games, posting 17 wins and 41 loses. For the 2010-2011 season, his injuries and legal troubles forced the Oilers to add a fourth goaltender (Martin Gerber) to the lineup as a backup plan, to assist struggling goaltender prospects Devan Dubnyk and Jeff Deslauriers.

For the remainder of his contract, Khabibulin will probably find himself backup to Dubnyk. But with a save percentage of .890 and a goal against average of 3.40 in 47 games last season, he may not even be cut out for that role.