Top 10 regrettable trade deadline deals

The Penguins dealt future Canucks captain Markus Naslund to Vancouver in '96 for Alek Stojanov. (CP Photo)

When it comes to pressure-packed jobs in the National Hockey League, the position of general manager is way up there. As a team’s GM, you’re responsible for not only the makeup of your hockey club, but also its current and future success.

The NHL trade deadline could well be the most stressful day of the year for most GMs. It is at this point in the season that he’s either looking to pick up a player or two to bolster his team’s roster for a playoff run or he’s looking to get rid of players to clear some cap space for the future.

The NHL trade deadline has led to some questionable and regrettable moves, ones that have fans saying “What the @#&%?”

Without further adieu, here are our top 10 regrettable trade deadline deals:

10. Calgary trades the Golden Brett to the Blues

In 1987-88, the Calgary Flames had a player only known then as Bobby Hull’s son.

Brett Hull was clearly not scoring at his father’s pace, and the Flames seemed to think that there was no future for him in Calgary. As such, the club shipped Hull to the St. Louis Blues for defenseman Rob Ramage and goaltender Rick Wamsley.

Yes, the Flames would go on to win the Stanley Cup the following season, but Hull, a Hall of Famer, would go on to score more than 700 goals and win two Stanley Cups in a career that spanned 18 seasons.

9. Dallas sends Neal packing to Pittsburgh

After putting up 55 points in 2009-10, the Dallas Stars gave James Neal a two-year contract extension worth $2.25 million.

As it turns out, the Stars ended up wasting that money because at the trade deadline the very next season, the Stars sent Neal and defenceman Matt Niskanen to the Pittsburgh Penguins in exchange for defenceman Alex Goligoski.

While Neal did not exactly click with the Penguins last season, he has certainly turned it around in this year’s NHL campaign and has made sweet music with Penguins star Evgeni Malkin.

8. Sharks acquire Campbell from the Buffalo Sabres

While all-star Brian Campbell is currently enjoying success with the Florida Panthers, he certainly let San Jose Sharks fans down back during the 2007-08 season.

At the trade deadline that season, Shark’ general manager Doug Wilson was looking for an offensive defenceman to bolster the team’s blue line and add some offence. To make that happen, Wilson went out and sent Steve Bernier and first-round pick to acquire the puck-moving defenceman.

Campbell would end up contributing 19 points in 20 games with the Sharks, but he did not do his job in the Stanley Cup Playoffs and ended up being a minus-3.

7. Devils drop everything to acquire Kovalchuk

With the Atlanta Thrashers, Ilya Kovalchuk was a scoring machine.

In eight-and-a-half seasons with the now-defunct Thrashers, Kovalchuk scored 328 goals. He was effective on even strength, on the power play, scored plenty of game-winning goals, and generally put up a silly amount of points on a consistent basis.

When the Thrashers were sinking in 2009-10 and looking to rebuild, they traded Kovalchuk to the New Jersey Devils on Jan. 28, 2010 for Johnny Oduya, two young, first-round prospects in Niclas Bergfors and Patrice Cormier, and their first two draft choices.

Since joining the Devils, Kovalchuk has not been the same scoring machine and certainly has not played up to his 15-year, $100-million deal. (Although, he has picked up his production this February.)

6. Oilers trade Satan to the Sabres

During 1996-97 the Edmonton Oilers did not like the kind of play they were getting from Miroslav Satan.

That season, Satan had only had 17 goals and 11 assists. For someone expected to do more, those numbers simply did not cut it for the Oilers.

At the trade deadline that season, the Oilers traded Satan to the Buffalo Sabres for Barrie Moore and Craig Millar. To say that this trade was lopsided would be an understatement.

Satan went on to score 40 goals two seasons later, followed by seasons of 29, 37, 26, and 29 goals. He would finish his career with 363 goals and 735 points. For the Oilers, Moore and Millar certainly did not have totals of Satan’s calibre.

5. The Lightning strike by trading Richards to the Stars

There was no doubt Brad Richards was making a bundle of money while playing for the Tampa Bay Lightning.

He was worth it. Richards helped lead the Lightning to a Stanley Cup in 2004 while also winning the Conn Smythe Trophy as the NHL’s most valuable player during the playoffs. However, the cash-strapped Lightning could not afford his $7.8 million cap hit.

As such, the Lightning swapped Richards and goaltender Johan Holmqvist at the 2007-08 trade deadline to the Dallas Stars for Jussi Jokinen, Jeff Halpern, and the Stars’ fourth-round choice in the 2009 NHL Entry Draft.

Richards ended up scoring 216 points in three seasons with the Stars before signing a nine-year, $60 million deal with the New York Rangers this past off-season.

4. Penguins deal Naslund to the Vancouver Canucks

Since the Pittsburgh Penguins already had the likes of Mario Lemieux, Jaromir Jagr, Ron Francis and several other offensively talented players, trading Markus Naslund at the 1996 trade deadline to the Vancouver Canucks for Alek Stojanov seemed to make perfect sense. Right?

Wrong. Naslund would go on to have 12 terrific years with the Canucks. He served as captain of the team for eight seasons, became the franchise leader in both goals and points, and had his number retired at the Rogers Arena last season.

Stojanov? Well, certainly nothing inspiring about his play, as he had seven points (two goals and five assists) in 107 NHL games.

3. Kings send Butch Goring to the New York Islanders

The Los Angeles Kings played a significant role in helping the New York Islanders to win four straight Stanley Cups in the 1980s.

At the trade deadline in 1980, the Kings traded Butch Goring to the Islanders for Billy Harris and Dave Lewis. While Harris and Lewis were certainly good hockey players, they were not Goring.

Goring went on to win four Cups, become a big-time contributor during the playoffs, and put up consistent numbers on Long Island for six seasons.

2. Oilers send Captain Canada to Long Island

After getting oh so close to winning a Stanley Cup in 2006, the Edmonton Oilers did something bold at the following season’s trade deadline.

Because the Oilers were unable to sign him to a contract extension during the off-season, the Oilers sent Ryan Smyth, who was scoring at a point-per-game pace at the time of the deal (31 goals and 22 assists for 53 points in 53 games) to the New York Islanders. In exchange for Smyth, the Oilers received prospects Robert Nilsson and Ryan O’Mara as well as a first-round selection in the 2007 NHL Entry Draft.

Smyth ended up helping the Islanders get into the Stanley Cup Playoffs, while Nilsson is no longer in the NHL and O’Mara has yet to really get a chance to shine for the Oilers.

1. Whalers trade Francis and Samuelsson to the Penguins

Prior to acquiring Ron Francis and Ulf Samuelsson at the trade deadline in 1991, no one was sure how the Pittsburgh Penguins would finish the season.

Their questions were answered in June, as both Francis and Samuelsson went on to help the Penguins win the franchise’s first Stanley Cup. To make this happen, the Penguins gave up John Cullen, Jeff Parker and Zarley Zalapski.

Francis and Samuelsson brought grit, skill and talent to the Penguins as soon as they were acquired. The duo ended up winning the Cup with Pittsburgh the following season as well.

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