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A look at some of the biggest deals in NHL history

by John Kreiser

There's not a hockey fan alive who doesn't think he can be a general manager -- after all, that's part of the fun of fantasy hockey. We all think we could make "the" deal, the one that turns our team into a Stanley Cup champion.

But as any real NHL GM can tell you, it's not as easy as it looks. Aside from dealing with salary cap considerations, pulling off an impact trade is a matter of making sure you're not trying to put square pegs in round holes (or vice versa).

Big trades are big gambles. Make the right one (like L.A.'s deal for Jeff Carter in late February) and you might win the Stanley Cup. Make the wrong one ... you get the picture.

As teams (and fans) talk about trades this offseason, here's a look at some of the biggest impact deals in NHL history.

Aug. 9, 1988 Jimmy Carson
Martin Gelinas
Three first-round picks
Wayne Gretzky
Marty McSorley
Mike Krushelnyski

More than a quarter of a century later, this is still the biggest trade in NHL history -- if not in the history of North American team sports.

Gretzky had just led the Oilers to their fourth Stanley Cup in five years, was rewriting the NHL record book on an annual basis and was part of a nucleus that was just reaching 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 Bruce McNall, the new owner of the Kings, who was looking to making a splash.

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, three first-rounders 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 hockey relevant in Southern California. Attendance soared as Kings games became celebrity-filled events. The Kings beat the Oilers in the playoffs that spring, and in 1993 made the first trip to the Stanley Cup Final in franchise history.

Over the years, Gretzky's impact off the ice has been even more important. The growth of hockey in warm-weather markets -- with talent already in the pipeline and more on the way every year -- 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. But 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 Bernie Nicholls
Steven Rice
Louie DeBrusk
Mark Messier
Future considerations

Three years after the Oilers dealt Gretzky, it was Messier's turn to go. Messier had become the Oilers' star and leader after The Great One was dealt, and he led them to the Cup in 1990. But after the Oilers lost the '91 Western Conference Finals to Minnesota, Messier requested a renegotiated contract, refused to report when he didn't get one and was dealt to New York just after the start of the season. 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, said he made the deal because he was desperate to bring in someone who could teach his team how to win. 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 New York rallied for a 2-1 win at the Montreal Forum, a place that had haunted them for decades.

By the end of the season, Messier had led the Rangers to the first Presidents' Trophy in franchise history; two years later, he scored the winning goal in Game 7 as the Rangers ended the longest championship drought in NHL history. He is still revered today as one of hockey's greatest leaders -- and in New York as the man who brought the Cup to the Big Apple.

The Oilers, who had also dealt away dynasty members such as 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.

Nov. 7, 1975 Phil Esposito
Carol Vadnais
Jean Ratelle
Brad Park
Joe Zanussi

It's easy to forget now how much the Bruins and Rangers loathed each other in the early and mid-1970s. The NHL's two doormats at the end of the Original Six era both revived at about the same time -- but the Bruins, led by Bobby Orr and Phil Esposito, were a little better. They beat the Rangers in the first round on the way to the Stanley Cup in 1970, then knocked off the Rangers again in the Final two years later.

This wasn't just a rivalry among fans -- the players on both teams couldn't stand each other. Park wrote a book that included a blast at the Bruins, while Esposito openly loathed the Rangers and everything about New York.

However, when both teams got off to slow starts in 1975-76, Rangers GM Emile Francis and his Boston counterpart, Harry Sinden, pulled off what's still one of the most shocking deals in NHL history. The Bruins sent Esposito, coming off a 127-point season, and Vadnais, their second-best defenseman, to the Rangers for Park, the NHL's second-best defenseman, and Ratelle, a slick center. Fans and players on both teams were stunned -- this was trading with the enemy.

But as usually happens, old enemies become new friends, and the newcomers quickly blended in.

In terms of performance, the Bruins got much the better of the deal. Park and Ratelle led Boston to the Final in 1977 and '78 and helped keep the Bruins among the NHL's top teams for the next decade. The Rangers missed the playoffs in their first two seasons after the trade, and Esposito was never the scorer in New York that he was in Boston -- though he did help the Rangers get to the '79 Final before retiring two years later.

Unfortunately for the Rangers, this deal led to another one that was a big win for the Bruins. In an effort to make Esposito more comfortable, the Rangers brought in his longtime right wing, Ken Hodge, the following summer while sending youngster Rick Middleton to Boston. But Middleton scored more than 400 goals for Boston, including five consecutive seasons of 40 or more. Meanwhile, Hodge had 62 points in 1976-77 as the Rangers missed the playoffs, was sent to the minors after a slow start in '77-78 and never returned to the NHL.

Dec. 6, 1995 Patrick Roy
Mike Keane
Andrei Kovalenko
Martin Rucinsky
Jocelyn Thibault

The Canadiens owe their last two Stanley Cups to Roy, who won the Conn Smythe Trophy as playoff MVP in both 1986 and 1993. But after being pulled during an 11-1 home loss to Detroit on Dec. 2, 1995, Roy stormed off the ice and then told team president Ronald Corey that he had played his final game as a Canadien.

He was right -- four days later, new GM Rejean Houle dealt Roy and team captain Keane to the recently relocated Quebec Nordiques, now playing in Denver. The price was a pair of young forwards along with 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 rise, Roy was the final piece of the puzzle. He added a third Stanley Cup 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-OT win in Game 4. He got ring No. 4 as the Avs won again in 2001. Roy 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 Phil Esposito
Ken Hodge
Fred Stanfield
Gilles Marotte
Pit Martin
Jack Norris

Bobby Orr's arrival in 1966 reinvigorated hockey 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, a hard-hitting defenseman who impressed a lot of people around the NHL. With Stan Mikita as their No. 1 center and Bobby Hull providing plenty of goals on 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 on a full-time basis.

The Bruins sent Marotte, Martin, a skilled center, 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 seasons. Hodge, playing on Espo's right wing, turned into a 50-goal scorer, while Stanfield became a superb second-line center who had at least 20 goals and 54 points in six consecutive seasons. The trio formed the nucleus of the Bruins' Cup-winning teams in 1970 and '72.

Martin was a solid player in his 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 Ron Francis
Ulf Samuelsson
Grant Jennings
John Cullen
Zarley Zalapski
Jeff Parker

The Penguins had never gotten as far as the final four before finally showing signs of life in 1990-91. But while they had stars like Mario Lemieux and Paul Coffey, there still had a couple of big holes -- notably a No. 2 center and a shutdown defenseman.

What the Penguins 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 -- he traded from his excess to fill his needs. Patrick sent 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.

As for the Whalers: Cullen had 16 points in 13 games 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 lymphoma in 1997; he made a brief comeback 18 months later, winning the Masterton Trophy just before retiring for good in '99. Zalapski had 20 goals in his first full season with the Whale and 65 points in his second, but never had more than 37 points again despite playing professionally until 2009-10.

June 20, 1992 Ron Hextall
Steve Duchesne
Kerry Huffman
Mike Ricci
Peter Forsberg
Chris Simon
Two first-round picks
Eric Lindros

The Nordiques took Lindros with the No. 1 pick in the 1991 NHL Draft, although he had asked them not to, saying he didn't want to play for Quebec. He sat out the 1991-92 season, playing 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 draft in Montreal. The Nords reached a deal with the Flyers, then wanted to negate it and accept a package from the Rangers. Ten days later, arbitrator Larry Bertuzzi decided that the trade with the Flyers was valid and awarded Lindros 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 as MVP in 1995.

But the Nordiques didn't do badly either. The key for them was Forsberg, the Flyers' first-round pick in 1991. By the time the franchise had relocated to Denver in 1995, the Swedish center was also a star -- and a big reason the Avs won the Stanley Cup in their first season in Colorado. He was also a key to their second Cup in 2001.

Lindros got the Flyers to the Stanley 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 was eventually forced to retire due to injury in 2006-07 after putting up 865 points in only 760 games.

June 6, 1986 Cam Neely
First-round pick
Barry Pederson

One of a general manager's biggest nightmares is giving up on a player too soon.

The Canucks made Neely, a local product, the ninth pick in the 1983 NHL 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. But 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 overall -- 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 Final in 1988 and '90. He had three 50-goal seasons before being forced to retire in 1996 due to a knee injury (he's now the team president). 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 pick they received to take Glen Wesley, who developed into an All-Star defenseman and went on to a 20-year career in the NHL.

Jan. 2, 1992 Doug Gilmour
Jamie Macoun
Kent Manderville
Ric Nattress
Rick Wamsley
Craig Berube
Alexander Godynyuk
Gary Leeman
Michel Petit
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 Hall of Fame center who was defensively solid and put up 127 and 111 points in his first two seasons with the Leafs, 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 came back to Calgary made any impact.

The deal set up the Leafs for their best post-expansion performance -- they made back-to-back trips to the conference finals in 1993 and 1994. The Flames missed the playoffs in 1992 and didn't win a playoff series again until 2004.

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