Ranking the Biggest Trades in NHL History on Wayne Gretzky Trade Anniversary

Twenty-five years ago today, the Edmonton Oilers completed a nearly unthinkable deal when they traded Wayne Gretzky to the Los Angeles Kings.

Gretzky was the best player in the game and the most dominating scorer in the sport's history. The Oilers had won four Stanley Cups with Gretzky leading the way. At the age of 27, Gretzky was at the peak of his powers.

Still, Edmonton owner Peter Pocklington was in financial trouble and needed money. He traded Gretzky to the Los Angeles Kings in a move that shocked the NHL and Canada.

Here's a look at the biggest trades involving the brightest stars that the league has ever seen.

13. Penguins Acquire Paul Coffey from Oilers (1987)

It wasn't as big as the Wayne Gretzky trade that would come a year later, but the trade that sent high-scoring defenseman Paul Coffey from the Edmonton Oilers to the Pittsburgh Penguins in 1987 sent shock waves throughout the NHL.

Coffey was arguably the NHL's second-greatest offensive defenseman behind Bobby Orr. He was engaged in a holdout with the Oilers, and when they wouldn't meet his price, Coffey was moved for winger Craig Simpson.

The Oilers also sent Dave Hunter and Wayne Van Dorp to Pittsburgh while the Oilers also acquired Dave Hannan, Moe Mantha and Chris Joseph.

While Coffey was not a prolific a scorer with the Penguins as he was in Edmonton, he scored 98 goals in his four full seasons with the Pens and 10 more in a partial season before he was traded to the Los Angeles Kings.

12. Red Wings Acquire Brendan Shanahan from Whalers (1996)

Brendan Shanahan was one of the key pieces of the Detroit Red Wings' dynasty.

The Red Wings had been a stellar team in the four years before Shanahan was acquired from the Hartford Whalers, but they had failed to win the Stanley Cup. Shanahan brought them a new level of credibility.

The Red Wings would go on to win three Stanley Cups in Shanahan's tenure with Detroit, including two in his first two years. The Whalers sent Shanahan and Brian Glynn to Detroit for Paul Coffey, Keith Primeau and a first-round draft pick in the 1996 trade.

11. Penguins Acquire Ron Francis from Whalers (1991)

The Pittsburgh Penguins were one of the best teams in the NHL late in the 1990-91 season when they acquired Ron Francis, Ulf Samuelsson and Grant Jennings for Zarley Zalapski, John Cullen and Jeff Parker.

After the trade was made, the Penguins went on to win back-to-back Stanley Cup titles. While the Penguins were clearly Mario Lemieux's team, they needed the grit and clutch play of Francis to get over the top.

Samuelsson also proved to be a key acquisition. While Cullen was productive in Hartford, the Whalers clearly got the worst of it in this vital trade.

10. Joe Thornton Traded from Boston to San Jose (2005)

The 2004-05 season had been eliminated by a lockout, and when the NHL returned the following year, the Boston Bruins were in disarray.

They struggled to win games and they appeared to have little chance to make the playoffs. Management swallowed hard and decided to trade former No. 1 draft pick Joe Thornton. Jumbo Joe was a talented passer with size and skill, but something was regularly missing from his game, particularly in postseason action.

The Bruins traded Thornton to San Jose where he would get a fresh start. The Bruins got Marco Sturm, Wayne Primeau and Brad Stuart. While the Bruins did not get star power in return for Thornton, Sturm gave them a lift with his speed and opportunistic play.

Thornton would become one of the best players in the league for the Sharks, but he would continue to have difficulties with his postseason performances.

9. Nordiques Trade Mats Sundin to Maple Leafs (1994)

The Quebec Nordiques had one of the brightest young stars in the NHL in flashy center Mats Sundin. However, they shocked the hockey world in 1994 when they traded him to the Toronto Maple Leafs.

Sundin would play 13 seasons for the Maple Leafs and he would be recognized as one of the franchise's best players in the post-expansion era. He was an eight-time all-star for the Maple Leafs.

The Nordiques traded Sundin, Garth Butcher, Todd Warriner and a first-round choice to Toronto for Wendel Clark, Sylvain Lefebvre, Landon Wilson and a first-round pick.

While the Nords would move and have great success as the Colorado Avalanche, the Leafs and Sundin were the clear winners in that trade.

8. Canucks Trade Cam Neely to Bruins (1986)

The Boston Bruins had been defeated in 18 straight playoff series by the Montreal Canadiens between 1943 and 1987. Cam Neely helped end that streak in 1988.

Neely was acquired by the Boston Bruins from the Vancouver Canucks along with a first-round draft pick for veteran center Barry Pederson in 1986. Neely had size, strength a powerful skating stride and a blistering shot. He would go on to score 50 or more goals three times and was voted into the Hall of Fame in 2005.

While Pederson had been very productive during his run with the Bruins, he was ordinary in Vancouver. The Bruins clearly got the decisive edge in this huge trade.

7. Maple Leafs Trade Frank Mahovlich to Red Wings (1968)

When the Toronto Maple Leafs traded superstar left wing Frank "The Big M" Mahovlich to the Detroit Red Wings in 1968, it was nearly as shocking as when the Edmonton Oilers would trade Wayne Gretzky two decades later.

The Maple Leafs had won the Stanley Cup in 1962, '63, '64 and '67, but they knew their veteran team was too old to make a run at another championship. Mahovlich, with his booming shot, was the centerpiece of a deal with Detroit. The Maple Leafs sent him, Pete Stemkowski, Garry Unger and the rights to Carl Brewer to the Red Wings for Paul Henderson, Norm Ullman, Floyd Smith Doug Barrie.

While Mahovlich would have excellent individual seasons in Detroit, he did not help the Wings become contenders. Henderson would go on to glory with Team Canada in 1972 vs. the Soviet Union, but the Maple Leafs never came close to a Stanley Cup after the trade.

6. Eric Lindros Traded to Philadelphia (1992)

Prior to getting drafted by the Quebec Nordiques in 1991, Eric Lindros was the clear-cut No. 1 selection.

Lindros appeared to have dominating ability and he was compared to Mario Lemieux and Wayne Gretzky in terms of talent and impact. As such a high-end player, Lindros decided to exercise his power by saying he would not play for the Nordiques.

He sat out the 1991-92 season and was just about to go back into the draft in 1992. Shortly before that happened, the Nordiques traded Lindros to the Philadelphia Flyers.

They also traded him to the New York Rangers, but an arbitrator awarded Lindros to the Flyers. The Nordiques received Steve Duchesne, Peter Forsberg, Ron Hextall, Kerry Huffman, Mike Ricci and Chris Simon), two draft picks and $15 million in exchange for Lindros.

Lindros had size, strength, speed and skill in abundance, and he scored 865 points in 760 games in his career. However, concussion problems and other injuries limited his overall impact and he was not able to join Lemieux and Gretzky in the pantheon of all-time great players.

5. Oilers Trade Mark Messier to Rangers (1991)

The New York Rangers had not won a Stanley Cup since 1940, and everyone associated with the team knew it. That included general manager Neil Smith, who made the key move in ending that dry spell when he acquired Mark Messier along with Jeff Beukeboom and David Shaw in 1991 by trading Bernie Nicholls, Steven Rice and Louie DeBrusk to the Edmonton Oilers.

At the time, the condition of Messier's knees made the deal less than a sure thing, but he was given a clean bill of health shortly after he arrived in New York.

Messier went from one of the smallest NHL cities to the biggest. He was not the least bit intimidated by his surroundings.

"I'm starting a second career," Messier told the New York Times, "and I'm every bit as confident about my second career as I was about my first."

Messier was telling the truth. He was superb with the Rangers, scoring 107 points in his first season and providing the leadership that the team desperately needed.

The Rangers would go on to win the 1994 Stanley Cup championship, with Messier guaranteeing a victory before an elimination game in the Eastern Conference Final against the New Jersey Devils, and coming through with a hat trick in that game. He also scored a goal and an assist in the Stanley Cup-clinching Game 7 vs. the Vancouver Canucks.

Trading for Messier was the best move in Rangers' franchise history.

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4. Patrick Roy Traded by Canadiens to Avs (1995)

Patrick Roy is considered to be one of the greatest goaltenders in NHL history. His legendary career with the Montreal Canadiens came to an abrupt halt Dec. 2, 1995 when he gave up nine goals in a game against the Detroit Red Wings.

When he was finally pulled in the second period, he eyed Montreal head coach Mario Tremblay with contempt and told team president Ronald Corey that he would never don a Montreal uniform again.

Roy and forward Mike Keane were traded to the Colorado Avalanche for goalie Jocelyn Thibault and forwards Martin Rucinsky and Andrei Kovalenko days later. Roy would go on to cap his Hall of Fame career by winning two Stanley Cups with the Avs. He has previously won two titles with the Habs.

3. Marcel Dionne Traded by Red Wings to Kings (1975)

Marcel Dionne was a budding star during his first four seasons with the Detroit Red Wings. However, the Wings were a struggling team and had failed to make the playoffs in any of those seasons.

Dionne was pushing for more money and Detroit traded him in 1975 to Los Angeles with Bart Crashley for Dan Maloney, Terry Harper and the Kings' second-round draft pick in 1976.

Dionne would go on to become a dominant star, scoring 50 or more goals six times in a Kings uniform. He teamed up with Charlie Simmer and Dave Taylor to form the Triple Crown line with the Kings.

2. Bruins Acquire Phil Esposito from Blackhawks (1967)

The Boston Bruins turned their fortunes around when Bobby Orr joined the team in 1966-67. However, even though Orr was arguably the greatest player in NHL history, he could not do it by himself.

The Bruins needed scoring, and general manager Milt Schmidt looked to Chicago for help. He coveted the size and scoring touch of Phil Esposito and the Bruins acquired the big center, Ken Hodge and Fred Stanfield for Pit Martin, Gilles Marotte and goalie Jack Norris.

Schmidt was hopeful he had made a good trade in 1967, but it turned out to be an overwhelming deal. Esposito would become the league's dominant goal scorer. He had 76 goals and 76 assists in 1970-71 for the rampaging Bruins and he teamed with Orr to give the team two Stanley Cup titles.

Esposito, Hodge and Stanfield would go on to score 1,156 goals for the Bruins, while Martin and Marotte would score 253 for the Blackhawks.

1. The Great One Traded to Kings (1988)

Canada went into shock when Wayne Gretzky was traded by the Edmonton Oilers to the Los Angeles Kings in 1988.

The catalyst for the deal was Edmonton owner Peter Pocklington's need for cash. Los Angeles owner Bruce McNall wanted to bring the game's biggest superstar to the Kings to make his team a major player in the Southern California sports scene.

Gretzky, Mike Krushelnyski and Marty McSorley went to Los Angeles, while the Oilers received Jimmy Carson, Martin Gelinas, three first-round draft choices (1989, 1991 and 1993) and $15 million.

Gretzky helped the Kings become contenders, and he led them to the Stanley Cup Final in 1993 where they lost to the Montreal Canadiens in five games.

Carson was supposed to be the key player for the Oilers because he had scored 55 goals in 1987-88 for the Kings. He had 49 goals in his first season with the Oilers, but he was traded early in the 1989-90 season to the Detroit Red Wings.

The Oilers won the 1990 Stanley Cup without Gretzky, but they have not won since.

It was a difficult trade for the team—and Canada—to endure.