20 Worst NHL Trade Deadline Deals of All Time

Brad KurtzbergContributor IMarch 18, 2013

20 Worst NHL Trade Deadline Deals of All Time

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    The NHL trade deadline is rapidly approaching (April 3 at 3:00 PM ET).

    The trade deadline became a hot topic after the Islanders acquired Butch Goring from the Los Angeles Kings in 1980 and Goring proved to be the final piece of the puzzle for a team that went on to win four consecutive Stanley Cup titles from 1980 to 1983.

    Since then, contending teams have tried to add that final piece of the puzzle. And teams that are out of the playoff race try to stock up on prospects and draft picks for players whose contracts are expiring or veterans looking for one more chance to win a title before they retire.

    Here is a look at the 20 worst trade deadline deals since the Islanders made that fateful deal for Butch Goring in 1980.

    As always, comments are most welcome. Feel free to mention any bad deals you feel I missed and explain why that deal belongs on our list.

20. Penguins Deal Glen Murray to the Kings

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    The Pittsburgh Penguins dealt Glen Murray to the Los Angeles Kings in exchange for Eddie Olczyk on March 18, 1997.

    By then, Olczyk was nearly finished with his last productive NHL season. He had 11 points in 12 games for the Penguins and then added one goal in five playoff games.

    Eddie O. spent one more year in Pittsburgh and scored just 11 goals and 22 points in 56 games. Then he was off to Chicago, where his NHL career ended after two injury-plagued seasons.

    Meanwhile, Murray spent more than four years with the Kings and twice scored 29 goals in a season.

    He went on to even greater success with the Bruins later in his career, but compared to what Olczyk had left in the tank, Murray was a steal.

19. Dallas Sends Ulf Dahlen to San Jose

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    The Stars dealt former Rangers first-round pick Ulf Dahlen to the Sharks for defensemen Doug Zmolek and Mike Lalor.

    Dahlen was playing top six minutes in Dallas and topped the 70-point mark, scoring 36- and 35-goal seasons before he was traded. He went to San Jose and became more of a defensive specialist who contributed on the third line, killed penalties and took important faceoffs. He spent more than three seasons with the Sharks in a full-time role.

    Zmolek lasted just parts of two seasons in Dallas, scoring two goals and 10 assists in 91 games before moving on to the Kings, while Lalor had two goals and four assists in 138 career games with the Stars.

18. San Jose Acquires Bill Guerin from St. Louis

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    The San Jose Sharks were Stanley Cup contenders in 2007 and as the trade deadline approached, the club looked to add that final player who could get the club over the top.

    They made a deal for Bill Guerin, a steady point producer and leader who was then playing with the Blues. Guerin was clearly seen as a rent-a-player by San Jose, but in exchange for the Worcester, Massachusetts, native, the Sharks gave up Ville Nieminen, Jay Barriball and a first-round pick in 2007.

    The result: Guerin scored nine points in 16 regular-season games for San Jose and added just two assists in nine playoff games. San Jose was ousted in the second round of the playoffs.

    The following summer, Guerin signed a two-year contract with the New York Islanders and the Sharks had nothing to show for their trade-deadline move to acquire Guerin.

17. Islanders Deal Chris Osgood to St. Louis

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    Goalie Chris Osgood was almost personally responsible for the Islanders' trip to the playoffs in 2001-02. The former Red Wings netminder won 32 games and had a 2.50 GAA that season.

    The Islanders lost a tough and physical seven-game series to the Maple Leafs that saw the home team win all seven contests. Again, Osgood played well for the Isles.

    The Islanders traded Osgood at the deadline the next season but didn't end up with much in return. The big part of the deal was forward Justin Papineau, who totaled nine goals and 16 points in 69 games for the Isles, and two draft picks. They picked forward Jeremy Colliton, who scored three goals and six points in 57 career NHL games with the Isles, and goalie Konstantin Barulin, who never left Russia.

    Osgood, meanwhile, was Detroit's starting goalie when they won the Stanley Cup in 2008 and helped them reach the Stanley Cup Final again in 2009. Osgood won more than 400 career games, 141 of them after leaving Long Island.

16. Flyers Acquire Ken Wregget

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    The Philadelphia Flyers have been searching for a goalie for a long time, really since Ron Hextall departed Philadelphia for the first time.

    One attempt to solve this problem came at the 1989 trade deadline, when the Flyers shipped a pair of first-round draft picks in 1989 to the Toronto Maple Leafs for goalie Ken Wregget.

    Wregget served as the Flyers' starter for one season and as a backup for most of two more, but never established himself as "The Man" in Philadelphia. In his one season as a starter, the Brandon, Manitoba, native had a losing record and an .892 save percentage. In the playoffs, he went 2-2 with the Flyers.

    The bottom line is that Wregget was not worth the two No. 1 picks the Flyers gave up to acquire him. The Flyers traded Wregget to Pittsburgh in 1989, where he spent the next six seasons.

15. Calgary Deals Brett Hull to St. Louis

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    On March 7, 1988, the Calgary Flames dealt Brett Hull and Steve Bozek to the Blues in exchange for defenseman Rob Ramage and goalie Rick Wamsley.

    On paper, this is a completely one-sided deal. Wamsley was a decent backup goalie for the Flames for three-and-a-half seasons. Ramage finished the 1987-88 season and played all of the following year for the Flames, scoring four goals and 23 points in 80 total regular-season games before heading on to Toronto.

    Meanwhile, Hull became one of the best goal scorers in NHL history with the Blues. In 10 seasons in St. Louis, "The Golden Brett" scored 527 goals.

    Bozek played only seven regular-season games and seven postseason games for the Blues before joining the Canucks the following season.

    But while Hull was far more productive than any player in the league during his decade-long stay in St. Louis, Ramage helped the Flames win their only Stanley Cup title in 1989, scoring 12 points in 20 playoff games for Calgary that year.

    On pure statistics, this trade was one of the most one-sided in NHL history, but the fact that the Flames won the 1989 Stanley Cup keeps it from being higher on our list.

14. Edmonton Trades Miro Satan to Buffalo

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    The Edmonton Oilers traded forward Miro Satan to the Buffalo Sabres on March 18, 1997, in exchange for Craig Millar and Barrie Moore.

    Moore played four games for the Oilers and failed to register a point. Millar scored four goals and six points in 36 games for Edmonton.

    Meanwhile, Satan spent more than seven seasons in Buffalo, scoring 224 goals and 456 points including a career-best 40 goals in 1998-99.

13. San Jose Acquires Brian Campbell from Buffalo

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    The San Jose Sharks were looking to add another rent-a-player in 2008 and acquired offensive defenseman Brian Campbell from Buffalo in an attempt to win their first championship.

    In exchange, the Sharks sent Buffalo forward Steve Bernier and a first-round draft choice in 2008, which Buffalo used to select Tyler Ennis.

    Campbell was productive in San Jose, scoring 19 points in 20 games during the regular season. In the playoffs, however, the talented defenseman had just seven points in 13 games and San Jose was eliminated in the second round.

    The following season, Campbell was off to Chicago, where he later helped the Blackhawks win a Stanley Cup.

    Meanwhile, Steve Bernier also ended up playing 17 games with Buffalo, scoring three goals and nine points.

    It was Ennis who tips the balance of this trade in Buffalo's favor. He is still only 23 and already has scored 45 goals and 112 points in 168 games with the Sabres, including 20 points in 28 games so far this season.

12. Buffalo Gets Ryan Miller from Florida

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    On March 23, 1999, the Florida Panthers and Buffalo Sabres made a trade that seemed minor at the time, but became a big deal.

    The Panthers acquired Mike Wilson from Buffalo in exchange for defenseman Rhett Warrener and a fifth-round draft choice.

    Wilson lasted for parts of three seasons in Florida, scoring four goals and 21 points, while Warrener played more than four seasons with the Sabres and was a steady force on their blue line.

    But then there's that fifth-round draft choice that was almost a forgotten part of the deal. It turned out to be a goalie from Michigan State named Ryan Miller.

    Miller won the Vezina Trophy in 2010 and won a silver medal for the United States in the 2010 Olympics in Vancouver.

    In the long run, Buffalo came out way ahead in this deal.

11. Chicago Trades Chris Chelios to Detroit

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    The Chicago Blackhawks thought that Chris Chelios was all but finished when they traded him to Detroit on March 23, 1999 in exchange for Anders Eriksson and a pair of first-round picks. They were wrong.

    Chelios would play in three more All-Star Games, help the Red Wings win a pair of Stanley Cups and be named to the first-team postseason All-Star team in 2001-02 after leading the league in plus/minus.

    Chelios lasted more than nine seasons in Detroit. Eriksson played one full season and small parts of two others in Chicago. Detroit won two Stanley Cups with Chelios, Chicago failed to win one with Eriksson.

10. Coyotes Send Keith Tkachuk to St. Louis

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    The Phoenix Coyotes traded their captain, Keith Tkachuk, to the St. Louis Blues at the trade deadline in 2001. In exchange, the Coyotes received Ladislav Nagy, Michal Handzus, Jeff Taffe and a first-round draft choice that they used to select Ben Eager. 

    Tkachuk spent more than five seasons in St. Louis, scoring more than 30 goals in each of the first three. The Blues traded him to the Thrashers at the trade deadline in 2007 before re-signing him the following summer. In all, Tkachuk spent more than eight seasons with St. Louis and topped the 20-goal mark in six of them.

    Meanwhile, none of the players the Coyotes acquired came close to matching Tkachuk's production with the Blues.

9. Toronto Deals Jason Smith to Edmonton

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    At the 1999 trade deadline, the Toronto Maple Leafs dealt defenseman Jason Smith to the Edmonton Oilers for a fourth-round pick in the 1999 NHL draft and a second-round pick in 2000.

    Smith became captain of the Oilers for five seasons, the same length of time that Wayne Gretzky held that post. As captain, he led Edmonton to the Stanley Cup Final in 2006.

    Meanwhile, the two draft picks became Jonathan Zion, who never played in the NHL, and Kris Vernarsky, who played 17 NHL games (all with Boston) and scored one goal.

8. Atlanta Sends Marian Hossa to Pittsburgh

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    Marian Hossa was the first Atlanta Thrashers player to score 100 points in a season.

    After negotiations on a new contract broke down, Atlanta dealt their high-scoring wing to the Penguins along with Pascal Dupuis for Colby Armstrong, Erik Christensen, Angelo Esposito and a first-round draft choice (who Atlanta used to select Daultan Leveille) on February 27, 2007.

    Yes, Hossa was a rent-a-player for Pittsburgh. He scored 10 points in 12 regular-season games for Pittsburgh before scoring 12 goals and 26 points in 20 playoff games. The Penguins reached the Stanley Cup Final before falling to Detroit in six games.

    Dupuis has been a steady winger for Pittsburgh and remains with the Penguins today. He scored a career-high 25 goals last season and was a member of Pittsburgh's 2008 Stanley Cup championship team.

    Atlanta didn't fare as well in this trade. Armstrong played a bit more than two seasons in Atlanta, scoring a career-best 22 goals in 2008-09. Christensen scored 26 points in 64 games over two seasons for the Thrashers. Esposito never reached the NHL, while Leveille has split this season between the AHL and ECHL after spending four years at Michigan State.

    Hossa turned out to be the perfect rent-a-player for the Penguins, while the Thrashers got much less than they anticipated in this deal.

7. St. Louis Sends Adam Oates to Boston

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    Adam Oates was one of the best passers in the NHL with the St. Louis Blues. He teamed with Brett Hull to form one of the most lethal duos in the NHL.

    On February 7, 1992, the Blues dealt Oates to Boston for Craig Janney and Stephane Quintal.

    Oates spent roughly five seasons in Boston and had scored more than a point per game in all of them. He had 97 assists and 142 points in 1992-93 and followed that up with 80 assists and 112 points in 1993-94.

    Janney had a couple of very good seasons with St. Louis, but didn't match Oates' production. Meanwhile, Quintal played one full season and part of another with the Blues before becoming a journeyman defenseman who played with Winnipeg, Chicago, the Rangers and Montreal.

6. Montreal Trades Vincent Damphousse to San Jose

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    The Montreal Canadiens traded Vincent Damphousse to the San Jose Sharks at the trade deadline in 1999 in exchange for a fifth-round pick in 1999 and a first- and second-round choice in the 2000 NHL Draft.

    Damphousse was productive in San Jose, spending more than five seasons with Team Teal and eventually being named captain of the Sharks.

    He scored 92 goals and 289 points in 385 games with San Jose and helped his new club become a steady contender in the tough Western Conference.

    Meanwhile, in return, the Habs used those picks to select Marc-Andre Thinel (fifth round), Marcel Hossa (first round) and traded the second-round choice in a separate deal with Columbus.

    Thinel never played an NHL game, while Hossa scored seven goals in two partial seasons with Montreal.

5. Phoenix Sends Daniel Briere to Buffalo

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    The Buffalo Sabres acquired Daniel Briere and a third-round pick at the 2003 trade deadline from Phoenix in exchange for forward Chris Gratton and a fourth-round selection.

    In the end, Buffalo ended up way ahead in this trade. Briere scored 92 goals and 230 points in three-plus seasons with the Sabres, including a career-best 95 points in 2006-07.

    Meanwhile Gratton scored only 11 goals and 30 points in 82 games in one-plus seasons with the Coyotes.

    As for the draft picks, neither Andrej Sekera (selected by Buffalo) nor Liam Reddox (picked by Phoenix) had an impact on this deal. 

4. Tampa Bay Trades Brad Richards to Dallas

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    Brad Richards helped the Lightning win a Stanley Cup in 2004. But by 2008, he was traded to the Dallas Stars along with Johan Holmqvist in exchange for goalie Mike Smith, forwards Jeff Halpern and Jussi Jokinen and a fourth-round draft choice.

    Richards spent more than three seasons in a Stars uniform and tied his career-high with 91 points in 2009-10. He scored more than a point per game with the Stars and was a leader on the team.

    Holmqvist played only two games for the Stars before returning to his native Sweden to tend goal in the Swedish Elite League.

    Smith played more than three seasons in Tampa Bay but never established himself as a steady starter. Helpern scored 26 goals in roughly three seasons with the Lightning and Jokinen scored eight goals in 66 games over parts of two seasons for the Bolts.

    In the end, Richards was by far the most productive player in this deal.

3. Toronto Deals Larry Murphy to Detroit

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    Toronto fans never really warmed to defenseman Larry Murphy during his brief tenure with the team. The Leafs were losing on the ice and Murphy was one of the highest paid players on the team.

    So, at the 1997 trade deadline, Toronto essentially gave the star defenseman away, sending him to the Red Wings for "future considerations."

    Murphy played more than four seasons for Detroit and helped the Wings win Stanley Cups in both 1997 and 1998. He was also selected to play in the 1999 NHL All-Star Game.

2. Pittsburgh Trades Markus Naslund to Vancouver

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    On March 20, 1996, the Vancouver Canucks made one of the best trades in NHL history when they acquired Markus Naslund from Pittsburgh for Alek Stojanov.

    Stojanov played all of 45 games at wing for the Penguins, scoring one goal and six points.

    Meanwhile, Naslund played in Vancouver until 2008 and is the franchise's all-time leading scorer with 346 goals and 756 points in 884 games.

1. Hartford Trades Ron Francis to Pittsburgh

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    The deal that sent Ron Francis from Hartford to Pittsburgh had more far-reaching consequences than any other deal on this list. It helped the Penguins win two straight Stanley Cups, while the Whalers lost their heart and soul and drifted until relocating to Carolina five years later.

    The complete trade saw the Whalers send Francis, defensemen Grant Jennings and Ulf Samuelsson to Pittsburgh for John Cullen, Jeff Parker and defenseman Zarley Zalapski.

    Francis lasted more than seven seasons in Pittsburgh and averaged more than a point per game, including two seasons of more than 100 points.

    Samuelsson became a big part of the Penguins defense. He spent more than four seasons with the Pens and contributed to both Penguins cup wins by playing a physical and agitating style that got under the skin of opposing forwards.

    Jennings also played on two Stanley Cup-winning teams with the Penguins.

    Meanwhile, Cullen only played one full season and parts of two others with the Whalers. He produced 77 points in 77 games during his only full campaign but possessed few of the leadership qualities that Francis gave the team.

    Parker played only four games for the Whalers and failed to register a point.

    Zalapski was a productive but wildly inconsistent defenseman for Hartford. He was capable of making some highlight-reel plays but also played inconsistent defense during his three seasons with the Whalers.

    The Penguins got the final pieces to two Stanley Cup titles. The Whalers lost their heart and soul. There was little doubt as to who won this deal.