There’s an abiding idiom in hockey trades. It says whoever got the best player in a deal wins the trade. If you get Wayne Gretzky you win every trade. After that, received wisdom of trades is more honoured in the breach than in the observance. Everyone has a theory. But all agree there’s no denying the impact of trades toward NHL success.

From their evolution as simple player-for-player swaps to the current version of trading players for draft picks, cash, future considerations, salary-cap space or actual humans, the art of swapping in the NHL has become a science, an art and an accounting exercise. Where once it was a pair of hockey-lifer GMs making deals, today’s moves require capologists, accountants, lawyers, agents and, often, the player’s family being onside before a deal can be approved by the NHL.

A whole new culture has grown up within the sport so that deals can be swung. As trades have become more complicated, they have concurrently become less of a burden on the moving parts involved. We’ve come off an offseason with a surprisingly modest number of intriguing deals.

With preseason games starting, to whet the ref’s whistle, here’s a list Rating The Top 25 Trades in NHL history from our next book Deal With It: The Most Impactful Trades In NHL history and How They Changed The Game (due later in 2023). (from ***** to ***)

1) August 9, 1988: Wayne Gretzky, Marty McSorley, and Mike Krushelnyski from Edmonton to Los Angeles for Jimmy Carson, Martin Gélinas, the Kings’ first rounders in 1989 (traded to New Jersey) , 1991 (Martin Rucinsky), 1993 (Nick Stadujar), and $15 million. *****

2) May 15, 1967: Phil Esposito, Fred Stanfield and Ken Hodge from Chicago to Boston for Gilles Marotte, Pit Martin and Jack Norris. ****1/2

3) October 4, 1991: Mark Messier and future considerations (Jeff Beukeboom) from Edmonton to the New York Rangers for Bernie Nicholls, Steven Rice, Louie DeBrusk and future considerations (David Shaw) ****1/2

4) December 6, 1995: Patrick Roy and Mike Keane from Montreal to Colorado for Jocelyn Thibault, Martin Rucinsky and Andrei Kovalenko ****1/2

5) June 30, 1992 Eric Lindros from Quebec City to Philadelphia for Steve Duchesne, Peter Forsberg, Ron Hextall, Kerry Huffman, Mike Ricci, Chris Simon, a 1993 1st round pick (#10-Jocelyn Thibault), a 1994 1st-Round pick, (#10-Nolan Baumgartner)) and $15 million in cash *****

6) March 3, 1968: Norm Ullman, Floyd Smith, Paul Henderson and Doug Barrie to Toronto for Garry Unger, Peter Stemkowski, Frank Mahovlich and Carl Brewer ****1/2

6A). January 13, 1971: Frank Mahovlich from Detroit to the Montreal for Guy Charron, Bill Collins and Mickey Redmond ****

7) March 10, 1980 Butch Goring from L.A. to New York Islanders for Dave Lewis and Bill Harris ****

8. November 1947 : Max Bentley from Chicago to Toronto for Gus Bodnar, Gaye Stewart, Bud Poile, Bob Goldham and Ernie Dickens ****

9) January 2, 1992: Gary Leeman, Alex Godynyuk, Jeff Reese, Craig Berube and Michel Petit from Toronto to Calgary for Jamie Macoun, Ric Nattress, Rick Wamsley, Kent Manderville and Doug Gilmour ****1/2

10) August 17, 1992 Dominik Hasek from Chicago to Buffalo for Stephane Beauregard and a fourth-round draft pick (Eric Daze) ****

11) July 23, 1957 Ted Lindsay and Glenn Hall From Detroit To Chicago for Johnny Wilson, Forbes Kennedy, Hank Bassen, Eric Preston ***1/2

12) June 28, 1994: Garth Butcher, Mats Sundin, Todd Warriner and 1994 first-round pick (#10-Nolan Baumgartner) from Quebec City to Toronto for Wendel Clark, Sylvain Lefebvre, Landon Wilson and 1994 1st round pick (#22-Jeff Kealty) ***1/2

13) May 22, 1970 : 1971 1st-round pick (#1-Guy Lafleur) and Francois Lacombe from Oakland to Montreal for Ernie Hicke and 1970 1st-round pick (#10-Chris Oddleifson) *****

14) Nov. 7, 1975: Phil Esposito, Carol Vadnais from Boston to New York Rangers For Brad Park, Jean Ratelle ****

15) October 1989: Tom Kurvers from New Jersey to Toronto for first-round pick (#3 Scott Niedermayer) ****

16) Nov. 30 2005: Joe Thornton from Boston to San Jose for Brad Stuart, Wayne Primeau and Marco Sturm ***1/2

17) December 20, 1995: Joe Nieuwendyk from Calgary to Dallas for Jarome Iginla ***1/2

18) Feb. 22, 1964: Andy Bathgate and Don McKenney from New York Rangers to Toronto for Dick Duff, Bob Nevin, Rod Seiling, Arnie Brown and Bill Collins. ***

19) March 7, 1988: Brett Hull from Calgary to to St. Louis for Rick Wamsley and Rob Ramage ***

20) June 29, 1990: Denis Savard from Chicago to Montreal for Chris Chelios ***

21) June 24, 1963: Dave Balon, Leon Rochefort, Len Ronson and Lorne “Gump” Worsley from New York Rangers to Montreal for Donny Marshall, Phil Goyette and Jacques Plante. ***

22) June 24, 2000: Mark Parrish and Oleg Kvasha from Florida to the New York Islanders for Roberto Luongo and Olli Jokinen ***

23) February 10, 1960: Red Kelly from Detroit to Toronto for Marc Rheaume ***1/2

24) October 10, 1930: King Clancy from Ottawa to Toronto for Eric Petting, Art Smith, cash ***

25) June 28, 1964: Ken Dryden and Alex Campbell from Boston to Montreal for Paul Reid and Guy Allen ****

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Bruce Dowbiggin @dowbboy is the editor of Not The Public Broadcaster A two-time winner of the Gemini Award as Canada's top television sports broadcaster, he’s a regular contributor to Sirius XM Canada Talks Ch. 167. Inexact Science: The Six Most Compelling Draft Years In NHL History, his new book with his son Evan, was voted the seventh-best professional hockey book of all time by bookauthority.org . His 2004 book Money Players was voted sixth best on the same list, and is available via http://brucedowbigginbooks.ca/book-personalaccount.aspx

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