A look at some of the biggest deals in NHL history

There's not a hockey fan alive who doesn't fancy himself a general manager. (Why do you think fantasy hockey has such a big following?) We all think we could make "the" deal, the one that turns our team into a contender or even a Stanley Cup champion.

However, as any real GM can tell you, it's not that easy. Aside from today's salary cap considerations, making an impact trade is a matter of making sure you're not trying to put square pegs in round holes.

Big trades are big gambles -- just ask GMs like Philadelphia's Paul Holmgren or San Jose's Doug Wilson, both of whom made major deals last month after their teams came up short in the playoffs. Both men know that their futures could ride on how well those trades work out.

Here's a look at some of the biggest impact trades in NHL history -- some benefitted both teams, while others worked out well for only one.

Aug. 9, 1988: Edmonton trades Wayne Gretzky, Marty McSorley and Mike Krushelnyski to Los Angeles for Jimmy Carson, Martin Gelinas, three first-round picks and cash

No trade in the NHL has had (or may ever have) the kind of impact this one had. Gretzky had just led the Oilers to their fourth Stanley Cup in five years, and the team's nucleus still was in its prime. But owner Peter Pocklington decided that Gretzky, whose contract was due to expire a year later, would become unaffordable and began shopping him. He found a willing partner in Kings owner Bruce McNall, who was looking to making an impact with a team that never had enjoyed much success.

The deal rocked the sports world. The idea that Gretzky could leave Western Canada for Southern California left Canadians in shock. The Kings gave up Carson, a 50-goal scorer who was just turning 20; Gelinas, a promising young forward, first-round picks in 1989, 1991 and 1993, and $15 million for hockey's greatest player and a pair of veterans in McSorley and Krushelnyski.

The trade was an instant win for the Kings. Gretzky immediately made the Kings relevant in Southern California, and attendance soared as Kings games became celebrity-filled events. The Kings beat the Oilers in the playoffs that spring, and in 1993 made the only trip to the Stanley Cup Final in franchise history.

Even more important was Gretzky's impact off the ice. The growth of hockey in warm-weather markets -- with talent already in the pipeline and lots more on the way -- may be Gretzky's biggest legacy to hockey, even more than all the records he holds.

The Oilers rebounded from their 1989 playoff loss to the Kings and won the Cup again in 1990 -- their fifth championship in seven years. They haven't won since, and haven't made the playoffs since 2006, the only time since their last Cup that they got to the Final.

Oct. 4, 1991: New York Rangers trade Bernie Nicholls, Steven Rice and Louie DeBrusk to Edmonton for Mark Messier and future considerations.

Three years after Gretzky was dealt, it was Messier's time to go. Messier had become a star in his own right in Edmonton after Gretzky was dealt and led the Oilers to the Cup in 1990, but after the Oilers lost to Minnesota in 1991 Western Conference Finals, Messier requested a re-negotiated contract, refused to report when he didn't get one and was dealt to New York after several weeks of jockeying back and forth. The price was Nicholls and two youngsters, one of whom (Rice) had been a first-round pick.

Rangers GM Neil Smith, whose franchise hadn't won the Stanley Cup since 1940, was desperate to bring in someone who could teach his team how to win rather than merely be satisfied by making the playoffs and perhaps winning a round.

Messier showed right away that he wasn't going to accept anything less than victory. In his first game as a Ranger, he set up the tying goal in the third period as the Rangers rallied for a 2-1 win at the Montreal Forum, a place that had haunted them for decades. Messier led the Rangers to the first Presidents' Trophy in franchise history in 1991-92; two years later, he scored the winning goal in Game 7 as the Rangers ended the longest championship drought in NHL history. He still is revered today in New York as "The Captain," and in hockey as one of the sport's greatest leaders.

The Oilers, who had also dealt away dynasty members Grant Fuhr, Paul Coffey and Jari Kurri, got back to the conference finals in 1992 before losing to Chicago, then failed to make the playoffs again until 1997. Nicholls played only 95 games with the Oilers before being traded to New Jersey, and neither Rice nor DeBrusk became an impact player.

Dec. 6, 1995: Montreal trades Patrick Roy and Mike Keane to Colorado for Andrei Kovalenko, Martin Rucinsky and Jocelyn Thibault

Roy was the key player in Montreal's 1986 and 1993 Stanley Cup victories, winning the Conn Smythe Trophy as playoff MVP on both occasions. His time in Montreal came to an end, though, when he stormed off the ice after being pulled during an 11-1 home loss to Detroit and on the way to the locker room told team president Ronald Corey that he had played his final game for the Canadiens.

Four days later, GM Rejean Houle dealt "St. Patrick" and team captain Keane to the Avs, who had just moved from Quebec. The price was a pair of young forwards and highly regarded (and French-Canadian) goaltender Thibault, a 20-year-old who was taken No. 10 by the Nordiques in 1993.

For the Avs, a talented young team on the way up, Roy was the last piece of the puzzle. He added a third Stanley Cup ring to his collection the following spring when he led Colorado to the first championship in franchise history, capping a sweep of Florida with a 1-0, triple-overtime win in Game 4. He led the Avs to another Cup in 2001 and finished his career two years later as the winningest goaltender in NHL history.

The deal didn’t work out so well for Montreal. All three of the players the Canadiens received had lengthy careers, but none made much of an impact for the Habs, who have yet to get back to the Final since the deal.

May 15, 1967: Chicago trades Phil Esposito, Ken Hodge and Fred Stanfield to Boston for Gilles Marotte, Pit Martin and Jack Norris

The arrival of Bobby Orr in 1966 offered signs of life in Boston, though the Bruins missed the playoffs in 1966-67 for the eighth consecutive season. Meanwhile, the Hawks were coming off the first regular-season championship in franchise history but had been upset in the opening round of the playoffs and felt they needed some tweaking.

They decided the player they wanted was Marotte, who had impressed a lot of people around the NHL with some of his big hits. With Stan Mikita as their No. 1 center and Bobby Hull providing plenty of goals at left wing, the Hawks were willing to trade Esposito, a 25-year-old center who was emerging as a big scorer -- and throw in Hodge and Stanfield, a pair of kids who hadn't been able to crack the lineup full-time.

The Bruins sent Marotte, skilled center Martin and reserve goaltender Norris to the Hawks in what turned out to be one of the steals of the century.

With plenty of help from Orr, Esposito set offensive records while winning five scoring titles in eight full seasons in Boston. Hodge, who became his right wing, turned into a 50-goal scorer, while Stanfield turned into a superb second-line center who had at least 20 goals and 54 points in six consecutive seasons. The trio was part of the nucleus of the Bruins' Cup-winning teams in 1970 and '72.

Martin was a solid player in 11 seasons in Chicago, but Marotte never became the kind of player the Hawks had expected and Norris played just 10 games for Chicago. The Hawks were among the NHL's best teams into the mid-1970s -- but if they hadn't made the trade, they might not have had to wait until 2010 to end their Stanley Cup drought.

March 4, 1991: Hartford trades Ron Francis, Ulf Samuelsson and Grant Jennings to Pittsburgh for John Cullen, Zarley Zalapski and Jeff Parker

After more than two decades in the NHL, the Pittsburgh Penguins finally were showing signs of life in 1990-91. But while the Penguins had stars like Mario Lemieux and Paul Coffey, they still had a couple of big needs -- notably for a No. 2 center and a shut-down defenseman.

What they did have were Cullen, who had stepped up when Lemieux was injured and piled up points, and Zalapski, a good offensive defenseman. With Lemieux getting healthy again, Craig Patrick did what all good GMs do -- traded from his excess to fill his needs -- sending Cullen, Zalapski and Parker to Hartford for a package that included Francis and Samuelsson.

Not even Patrick could have imagined how well the deal turned out. With Francis as the No. 2 center behind Lemieux and Samuelsson providing the kind of crease-clearing help the Penguins had never had, Pittsburgh rolled all the way to the first Stanley Cup in franchise history that spring, then repeated the following year.

Cullen had 16 points in 13 games with the Whalers at the end of 1991-92, added 77 points in as many games the following season, but was dealt to Toronto after a slow start in 1992-93. His career was interrupted when he was diagnosed with non-Hodgkin's lymphoma in 1997; he made a brief comeback 18 months later, winning the Bill Masterton Trophy just before retiring for good in '99. Zalapski had 20 goals in his first full season with the Whalers and 65 points in his second, but never had more than 37 points again despite playing professionally until 2009-10.

Jan. 2, 1992: Calgary traded Doug Gilmour, Jamie Macoun, Kent Manderville, Ric Nattress, and Rick Wamsley to Toronto for Craig Berube, Alexander Godynyuk, Gary Leeman, Michel Petit, and Jeff Reese

The Flames still had the core of their 1989 Cup team as 1991 turned into 1992, but the window for a second championship run appeared to be closing. Toronto GM Cliff Fletcher, who had built the Cup-winning team in Calgary, had moved on to the Leafs and fleeced his former team by getting Gilmour, a high-scoring center who also was defensively solid, two useful defensemen in Macoun and Nattress, and a good backup goaltender in Wamsley. Leeman, a former 50-goal scorer, was the centerpiece for the Flames, but none of the five players who went to Calgary made major impacts.

The deal set the Leafs for their best post-expansion performance, going to conference finals in 1993 and 1994. The Flames missed the playoffs in 1992 and didn't win a playoff series again until 1994.

June 20, 1992: Philadelphia traded Ron Hextall, Steve Duchesne, Kerry Huffman, Mike Ricci, Peter Forsberg, Chris Simon, two first-round picks and cash to the Quebec Nordiques in exchange for the rights to center Eric Lindros

The Nordiques took Lindros with the No. 1 pick in the 1991 Entry Draft, although he had asked them not to because he didn't want to play for Quebec. He sat out the 1991-92 season, playing junior hockey and for Team Canada at the Winter Olympics, before the Nordiques decided they would have to trade him.

The specter of Lindros being dealt overshadowed the 1992 Entry Draft in Montreal. The Nords reached a deal with the Flyers, then tried to negate it and accept a package from the Rangers. Ten days later, arbitrator Larry Bertuzzi ruled that the trade with the Flyers was valid and awarded him to Philadelphia.

From the start, it was obvious that on the ice Lindros was every bit as good as advertised. With good speed, soft hands and enormous size, he quickly became a star, winning the Hart Trophy in 1995.

However, the Nordiques didn't do badly, either. The key for them was Forsberg, a former No. 1 pick by the Flyers. By the time the franchise had relocated to Denver in 1995, the Swedish center also was a star -- and a big reason the Avs won the Stanley Cup in their first season in Colorado.

Lindros got the Flyers to the Cup Final in 1997, only to have his team swept by Detroit. But beginning in 1998, he suffered a series of concussions that took its toll on his career. He sat out all of the 2000-01 season and eventually was forced to retire due to injury in 2006-07 after putting up 865 points in only 760 games.

June 6, 1986: Vancouver traded Cam Neely and a first-round pick to Boston for Barry Pederson

Talk about giving up on a player too soon.

The Canucks made Neely, a British Columbia native, the ninth pick in the 1983 Entry Draft and brought him to the NHL as an 18-year-old. He had 31, 39 and 34 points in three seasons with Vancouver while taking 137 and 126 penalty minutes in the last two. Also, coach Tom Watt wasn't thrilled with the youngster's defense, and on Neely's 21st birthday, the Canucks sent him along with their first-round pick -- the No. 3 choice -- to Boston for Pederson, who had scored 129 goals in three seasons from 1981-84.

It was apparent almost from the start that the Bruins had made a killing. Neely became the prototypical power forward, scoring 36 goals in his first season with the B's and powering them to the Stanley Cup Final in 1988 and '90. He had three 50-goal seasons before being forced to retire in 1996 due to a knee injury. Pederson had 24 goals in his first season with Vancouver but never broke the 20-goal mark again. To make things even worse, the Bruins used the draft pick acquired in the trade to take Glen Wesley, who developed into an All-Star defenseman who played 20 years in the NHL.

March 10, 1980: Los Angeles traded Butch Goring to the New York Islanders for Dave Lewis and Billy Harris

Sometimes it's not how good the player you get is, it's how he fits in. Such was the case with Goring, whose acquisition proved to be the missing piece of the puzzle for the Islanders.

Goring was a speedy center who was 31 and had averaged a point a game for the previous four seasons and was doing so again with an up-and-down Kings team. L.A. felt he was replaceable and sent him to the Islanders at the trade deadline for Harris and Lewis, both solid players who had been instrumental in the team's rise from their disastrous first season into Cup contenders.

Goring's speed and skill made him a perfect No. 2 center on a team that already had stars like Bryan Trottier and Mike Bossy up front. He had 11 points in 12 games as the Isles went undefeated down the stretch of the regular season, then added 19 points as they won the first Cup in franchise history.

His offensive numbers on Long Island never were as good as they were in L.A., but Goring seemed to save his best for playoff time, winning the Conn Smythe Trophy in 1981 and playing a key role on the Isles' four straight Cup winners. The Isles let him go to Boston in 1984-85, and he retired at the end of the season.

Harris had 20 goals for the Kings in 1980-81 but never scored that many again and was 32 when he retired in 1984. Lewis was a solid defensive defenseman until calling it quits in 1988.

May 26, 1976: Boston traded Ken Hodge to the New York Rangers for Rick Middleton

As they did in the Cam Neely trade, the Bruins acquired a rising star at the cost of a player whose best years were behind him.

This trade had its roots in a blockbuster from the previous October, when the Bruins and Rangers exchanged stars -- Phil Esposito and Carol Vadnais went to the Rangers for Jean Ratelle and Brad Park -- in what was, at the time, perhaps the most shocking deal in NHL history. The two teams were fierce rivals, and both teams (and their fans) were stunned by the trade.

Esposito had thrived with Hodge on his right side in Boston and wanted his old linemate in New York for the 1976-77 season. The price was Middleton, a speedy 23-year-old who had scored 46 goals in his first two seasons with the Rangers.

Unfortunately for the Rangers, it turned out they traded Middleton's future for Hodge's past. Middleton scored more than 400 goals for Boston and had five consecutive seasons of 40 or more. He helped the Bruins to the 1977 and '78 Stanley Cup Final and kept Boston among the NHL's best teams through the 1980s.

The other side of the trade didn't work as well. Hodge had 62 points in 1976-77 as the Rangers missed the playoffs, was sent to the minors after a slow start in 1977-78 and never returned to the NHL.