The Calgary Flames won the Stanley Cup in 1989. After the parade, the team began its inevitable decline. Sure, Cliff Fletcher left for a gig in Toronto. Sure, the Canadian dollar was tanking and the economics of sport made it challenging to keep the band together. But smart asset management could’ve made a transition smooth.

Smart asset management is not what the Flames ending up with as a strategy.

The season was 1991-92. The Flames were three seasons removed from their Stanley Cup parade. Fletcher had departed, replaced by assistant GM (and protege) Doug Risebrough as GM. Risebrough had inherited a good core, some fundamental economic challenges, and no real playbook. Worse, Doug Gilmour – arguably the best all-around player on the team – was feeling undervalued and wanted a new contract.

In December 1991, Gilmour and the Flames went to arbitration. Via Wikipedia, here’s a quick rundown of the situation:

An off-season salary dispute with Flames’ general manager Doug Risebrough carried into the 1991–92 season. Gilmour, who was playing the option year of his contract at a salary of US$450,000 was unable to reach a deal with the team on an extension. The dispute went to arbitration where the Flames offered a raise to $550,000 while he asked for $1.2 million and was expecting a settlement worth around $800,000. The arbitrator’s decision, made in December 1991, amounted to $750,000 per season for two years, but left Gilmour angry and bitter. He alleged that executives with the team and league had tampered with the process – the arbitrator attended a Flames game with team management on the night before the hearing, while NHL President John Ziegler sent a letter to the arbitrators. Gilmour, who remained active with the Flames throughout the process, had scored 38 points in 38 games. Following the decision, he requested a trade out of Calgary and threatened legal action. Gilmour led the Flames to a 3–2 overtime victory over the Montreal Canadiens with a goal and an assist on New Year’s Eve then walked out on the club on January 1, 1992.

As an aside, there are many reasons why the NHL and NHLPA handle arbitration in the off-season and got rid of option years in contracts – bitter situations like Gilmour’s are prime among those reasons.

Poor Risebrough had his back against the wall, basically forced to trade Gilmour quickly or allow the situation to snowball as a distraction for a potentially playoff-bound team. But the potential deal itself rapidly snowballed from a delicate move that required surgical precision into a behemoth, one of the largest trades in NHL history.

On January 2, 1992, the Flames traded Gilmour, Ric Nattress, Jamie Macoun, Kent Manderville and Rick Wamsley to Toronto for Gary Leeman, Craig Berube, Alexander Godynyuk, Michel Petit and Jeff Reese.

In other words: the Flames traded arguably their best player (28), their shutdown defensive pairing (29 and 30), their backup goalie (32) and their top prospect (20) in exchange for a rugged winger two years removed from a 50 goal season (27), a pair of depth defenders (23 and 27), a checking forward (26) and Toronto’s backup goalie (25).

On the surface, the trade had a lot of similarities to the types of trades Fletcher made during his heyday with the Flames except rather than make four trades (as he did in November 1981) Risebrough aimed to do it with one. But doing a lot of things at once, you lose precision, and instead of getting assets of value you get… a bunch of guys who themselves didn’t have a great deal of value as future assets.

  • Leeman played 59 games for the Flames and was traded to Montreal for Brian Skrudland
  • Berube played 113 games and was traded to Washington for a fifth round pick
  • Godynyuk played 33 games and was claimed by Florida in the expansion draft
  • Petit played 134 games and left as a free agent
  • Reese played 39 games and was traded to Hartford for Dan Keczmer

The Dion Phaneuf trade was rushed and sloppy work, but the Flames still landed Matt Stajan (who played over 500 games for them). The Gilmour trade? Woof.

The remainder of the tear-down of the 1989 Flames team was conducted in a piecemeal fashion, but at least they got value when they did so.