Sometimes, the magnitude of a trade isn’t realized until years later, when the players involved have finished their careers. Other times, a colossal mess-up on one side of a trade is realized more immediately.
There is always a winner and a loser in a trade. Rarely, both teams benefit from a swap. That holds true in the NHL just as much as any other sport. There have been plenty of trades over the years where one team has fleeced the other.
These are arguably the 10 best NHL trades of all-time — at least for one of the teams involved.
10. St. Louis Blues Acquire Brett Hull
The Blues sent the Flames defenseman Rob Ramage and goaltender Rick Wamsley in exchange for Hull and left wing Steve Bozek. While the Flames did go on to win the Stanley Cup in 1989, it was the Blues who received the better end of this deal as Hull went down as one of the best the NHL players ever.
9. Jarome Iginla to Calgary, Joe Nieuwendyk to Dallas
It’s not too often that a trade benefits both sides, but in the case of the Jarome Iginla-Joe Nieuwendyk deal, that’s exactly what happened. In 1995, the Dallas Stars and Calgary Flames completed a trade that ended up involving two Hall of Famers.
Iginla was traded to the Flames while Nieuwendyk was sent to the Stars. The Stars went on to win a Stanley Cup a few years later when Nieuwendyk was the Conn Smythe winner and the playoff MVP as well. Iginla became the Flames' all-time leading scorer and one of the best players in NHL history.
It's the rare win-win trade in any league.
8. Dominik Hasek Heads to Buffalo
On August 7, 1992, the Buffalo Sabres completed a trade for one of the greatest goalies in NHL history. The Sabres acquired Dominik Hasek from the Chicago Blackhawks in exchange for Stephane Beauregard and a 1993 4th-round pick, which ended up being Eric Daze.
Hasek spent the majority of his Hall-of-Fame career in Buffalo. He also won six Vezina Trophies during his tenure in Buffalo. He did end up winning two Stanley Cups as well, although neither were in Buffalo.
Still, the Sabres landed one of the best goalies of all-time for nine seasons for mere pennies on the dollar.
7. Ron Francis to Pittsburgh
The Pittsburgh Penguins made a franchise-changing trade back in 1991 when they acquired Francis and others from the Hartford Whalers. The Whalers traded the Penguins Ron Francis, Grant Jennings and Ulf Samuelsson in exchange for John Cullen, Jeff Parker and Zarley Zalapski.
Francis, who was voted one of the NHL’s 100 greatest players of all-time, was second all-time in career assists (1,249), fifth in career points (1,798) and 27th in career goals (549) when he retired in 2004.
He was a big contributor to the Penguins’ 1991-92 Stanley Cup-winning season.
6. Cam Neely Joins the Bruins
On June 6, 1986, the Boston Bruins acquired Cam Neely from the Vancouver Canucks. Not only did the Bruins get Neely, they also acquired the Canucks’ first-round pick, which was used to draft Glen Wesley. In exchange, the Bruins sent the Canucks Barry Pederson.
Neely never won a Stanley Cup as a player in Boston, losing in the finals twice, but he was part of the Bruins front office that won the Stanley Cup in 2011. Despite not winning the Cup as a player, Neely went on to have an excellent career and without the trade, likely wouldn’t have been a part of the Bruins’ front office.
5. Mark Messier Moves to the Rangers
On October 4, 1991, Mark Messier was traded by the Edmonton Oilers, along with future considerations, to the New York Rangers in exchange for Bernie Nicholls, Steven Rice and Louie DeBrusk. Messier, who won five Stanley Cup titles with the Oilers, made an immediate impact on the Rangers.
Messier led the Rangers to a league-best record in both 1991-92 and 1993-94. The Rangers, led by Messier, ended a 54-year championship drought in 1994 when they finally won the Stanley Cup.
4. Eric Lindros Becomes a Flyer
Arguably one of the most peculiar trades sports altogether, Eric Lindros was sent to the Philadelphia Flyers in 1992.
Lindros was drafted by the Quebec Nordiques with the first overall pick in the 1991 NHL Entry Draft. However, Lindros didn’t want to play for the Nordiques and instead held out the entire year. At just 18, Lindros was considered the best junior prospect in NHL history.
Lindros told the Nordiques he would sit out a second season and re-enter the 1993 NHL Draft so the Nordiques decided to finally trade away his rights. The Nordiques traded him to both the Philadelphia Flyers and the New York Rangers. After a week-long arbitration, it was determined that the Flyers had the rights to Lindros. In exchange, the Nordiques received Steve Duchesne, Peter Forsberg, Ron Hextall, Kerry Huffman, Mike Ricci, Chris Simon, two draft picks and $15 million.
3. Phil Esposito to Boston
On May 15, 1967, the Boston Bruins acquired Phil Esposito, Ken Hodge Sr. and Fred Stanfield from the Chicago Blackhawks in exchange for Jack Norris, Pit Martin and Gilles Marotte.
Esposito led the league in goals for six-straight seasons from 1969-70 to 1974-75. The Bruins won a franchise-record 57 games in 1970-71 when Esposito scored a career-high 76 goals. Even Hodge tallied 40 or more goals for the Bruins three times.
A Boston dynasty was born following the trade with Chicago. The Bruins won two Stanley Cups during Esposito’s tenure. They were the last Stanley Cups for the Bruins until their win in 2011.
2. Avalanche Acquire Patrick Roy
Arguably the greatest goalie in NHL history, Patrick Roy, was traded from the Montreal Canadiens to the Colorado Avalanche on December 6, 1995. Roy was sent to Colorado along with Mike Keane in exchange for Andrei Kovalenko, Martin Rucinsky and Jocelyn Thibault.
Roy was traded to Colorado for next to nothing due to an incident with the Canadiens a few days prior. Roy and the Canadiens had a strained relationship because of Mario Tremblay being hired as the new head coach. Following a “humiliating” game in which Roy was not removed from net by Tremblay until after Roy allowed nine goals, Roy said he was done playing in Montreal.
Instead of trying to mend the relationship between Roy and Tremblay, the Canadiens instead decided to trade Roy to the Avalanche for next-to-nothing. A trade which helped turn the Avalanche franchise around.
1. Wayne Gretzky Heads to Los Angeles
The greatest player in NHL history was traded on August 9, 1988. The Oilers sent Wayne Gretzky, along with Marty McSorley and Mike Krushelnyski to the Los Angeles Kings for Jimmy Carson, Martin Gelinas, $15 million in cash and the Kings’ first-round picks in 1989, 1991 and 1993.
A trade that upset so many Canadians that they even tried to have the Canadian Parliament block the trade, Gretzky was “sold not traded” to the Kings in his words. While the Kings never won a Stanley Cup during Gretzky’s tenure, they still had the greatest hockey player of all-time for eight seasons.
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