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/

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 ****

Sign up today for Not The Public Broadcaster newsletters. Hot takes/ cool slants on sports and current affairs. Have the latest columns delivered to your mail box. Tell your friends to join, too. Always provocative, always independent.  https://share.hsforms.com/16edbhhC3TTKg6jAaRyP7rActsj5

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

In case you hadn’t noticed. Celebrity Sports Ownership is all the rage. When the Ottawa Senators were for sale Ryan Reynolds, Snoop and The Weeknd were all mentioned among the bidders (that eventually went to Montreal businessman Michael Andlauer). LeBron James now holds a minority position with Liverpool FC.

Jay-Z owns part of the Brooklyn Nets, Usher a piece of the Cleveland Cavaliers while Fergie of Black Eyed Peas fame also partly owns the Miami Dolphins. Gloria and Emilio Estefan, Marc Anthony, and tennis superstars Serena and Venus Williams are owners of pro sports teams. Famously, Elton John owned Watford FC, although he’s now just an honorary chairman.

And, of course, Reynolds and Rob McElhenney used a documentary TV series that showed their Welsh Wrexham soccer team promoted to the FA’s League Two. What’s the attraction?

Clearly a little PR is always a good thing. But sports team ownership has also become a lucrative equity play. As BMO reports, “The average compound annual growth rate since the last purchase price…  is 15 percent, a meaningful outperformance to the TSX and S&P.  Forbes estimates the Toronto Blue Jays are currently worth US$2.1 billion or roughly C$2.85 billion.

Based on recent sports franchise transactions, expansion fees and annual estimations of franchise values by Forbes Magazine, an $8 billion enterprise value is easily defendable for the Jays’ owners MLSE (who also own the Maple Leafs, Toronto FC and Argonauts).”

It’s the same across the major pro sports leagues. The estimated average franchise value in the NFL since 2013 is $5.1B with a compound annual growth rate (CAGR) of 16 percent; in the NBA it is $2.9B with a CAGR of 18 percent. For MLB it is $2.3B with a CAGR of 12 percent; the NHL is $1.0B with a CAGR of 11 percent; while MLS is $0.6B with a CAGR 21%.

But, BMO cautions, owning a sports franchise is considered “an equity investment strategy rather than a cash flow or income play.” In other words, don’t think that ticket sales and hot dogs are going to make you rich. (Although the NHL’s salary cap, which guarantees owners’ profits is a sweet deal.) The key is sports media which is thriving despite the move to cord cutting..

Sports media rights contracts have grown in tandem with franchise valuations. Not to be ignored in the advertising growth and viewer interaction is the bear knowns as legalized sports betting. Betting companies are flooding the airwaves with commercials while bettors tune in to watch how their selections work out. The casinos and online shops have replaced lower-paying traditional advertisers who’ve dropped off.

In Canada, league or team ownership of broadcast properties is still common. For that reason the real value of those broadcast rights is often opaque. (We had some irritated pushback from Rogers and Bell for writing on this tidy arrangement in the mid 2010s, forcing some limited disclosures). Rogers Sportsnet and TSN own (via MLSE) own a stable of teams in MLB, NHL, CFL and MLS. Good luck finding out what they pay themselves for media rights.

It’s more open in the U.S. Since the New York Yankees pioneered the YES network in 2002— sparking multiple imitators in other markets—the move in the U.S. has been away from outright ownerships of regional sports networks. A number of RSNs in the U.S. are either in bankruptcy or nearing it. Digital and network sources are now absorbing these sources. ESPN, via its owner Disney, is looking to find partners for its many broadcast properties as their bottom line in general has suffered.

Still, ESPN’s legacy business generates revenue and operating income of approximately $12.5 billion and $4.0 billion in 2023. It remains to be seen what new model emerges in the U.S. to answer cord cutting and the death of conventional TV. The NFL’s experiment on Monday, having two MNF games compete on separate networks is one experiment.

In Canada’s monopolistic market, “TSN/RDS penetration rates have declined at a quicker pace than ESPN over the past 10 years. ESPN penetration has dropped from 81 percent of U.S. households in 2013 to 56 percent in 2022, while TSN/RDS penetration has decreased from 89% of Canadian households in 2013 to 49 percent in 2022.

In addition, BMO admits that cord cutting is a thing. “SportsNet subscribers have decreased -23 percent to 5.8 million over the same period. Subscriber and advertising revenues are 60 percent and 40 percent of total revenue, respectively. Since 2017, TSN revenues have increased 13 percent. TSN subscribers have decreased -29 percent to ~7.8 million over the same period.”

But! In the last five years, TSN and SN have increased advertising revenues by 13 percent and 15 percent respectively. The same figure for the top five Canadian non-sports channels (collectively) is six percent. Thank you legalized wagering in Ontario. So who wouldn’t want a piece of this action, especially in Canada?

The red flag in this surging equity market comes in the form of smaller Canadian NHL markets. The Senators sale for $950 suggests a healthy interest in owning, but the Sens sale was also tied into the new LeBreton Flats arena. Ownership or control of a Canadian arena means more than NHL games. It also includes revenue from concerts, rallies, monster-truck events etc.

Even with that can Andlauer produce a winner just two hours from the Montreal Canadiens market? Likewise, the Winnipeg Jets are desperately in need of a larger arena to replace the 15,321 Canada Life Centre. Having Canada’s richest man, David Thomson, as an owner is no guarantee of getting one. And should Thomson tire of being the saviour of a losing Jets hockey property, who in that market has C$1-2B lying around needed to fund the franchise properly?

Likewise, the Calgary Flames. Despite the political press conference this summer about as new agreement the arena that management promised by 2013 has still not seen a shovelful of dirt turned over. The latest gaffe was architect’s drawings for the rink being rejected by the NHL due to inadequate dressing-room space. Start again.

Should the rink not be available till 2025-26 will an evolving ownership group still be interested in shelling out the money to keep the Flames (and Stampeders, Roughnecks and Hitmen) operating in Calgary? And if they don’t, because losing sucks? While energy-rich Calgary has plenty of billionaires, few will want to risk the money needed to keep a competitive team in a small market.

Connor McDavid’s brilliance plasters over the same small-market crack in Edmonton. Yes, they have their new building, but can owner Darryl Katz fund the moves need to keep his stars and build a winner? Vancouver, owned by the Aqulini family, has a larger market base, but with Seattle Kraken just two hours away can they too write the cheques needed to create the first Stanley Cup winner since the Canucks entered the NHL in 1970.

If these Canadian markets do survive longterm it might have to be with foreign ownership. Certainly there is money to be made riding the equity train. But there also no guarantees that those carpetbagger owners might replicate the Montreal Expos and scoot to richer markets.

Sign up today for Not The Public Broadcaster newsletters. Hot takes/ cool slants on sports and current affairs. Have the latest columns delivered to your mail box. Tell your friends to join, too. Always provocative, always independent.  https://share.hsforms.com/16edbhhC3TTKg6jAaRyP7rActsj5

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