In the 1980s the Calgary Flames were a powerhouse. Driven by their desire to beat the Edmonton Oilers and win some post-season hardware, they eventually toppled their northern rivals and made two trips to the Stanley Cup Final.

The 1990s weren’t nearly as kind to the Flames. Some of their troubles were due to the NHL’s economics, with the declining Canadian dollar leading to a rather drastic sell-off of talent as the decade progressed. But easily the biggest setback to the organization’s fortunes was self-inflicted.

Twenty-five years ago today, the Flames made one of the worst trades in the history of the National Hockey League when they traded away Doug Gilmour.

In the midst of a contract dispute with the club, Gilmour left the team on New Year’s Day 1992. The whole dispute stemmed from an arbitration award that he didn’t agree with, and it became abundantly clear that the relationship was fractured beyond repair. Gilmour likely wouldn’t come to terms with the Flames on an extension. Below .500 and in the midst of a season that would see them miss the playoffs for the first time in nearly 20 years, the Flames needed to make a move.

A day after Gilmour walked out on the team, general manager Doug Risebrough and his old mentor Cliff Fletcher (in a new job as Toronto’s head honcho) combined on the largest trade in NHL history.

Going to Toronto:

Gilmour, 28, arguably Calgary’s best player and a 1989 Stanley Cup winner

Ric Nattress, 29, a big-bodied right-shot defender and a 1989 Stanley Cup winner

Jamie Macoun, 30, a responsible left-shot defender and a 1989 Stanley Cup winner

Rick Wamsley, 32, Calgary’s backup goalie and a 1989 Stanley Cup winner

Kent Manderville, 20, a two-time World Junior gold medalist and one of Calgary’s top prospects

Coming to Calgary:

Gary Leeman, 27, two years removed from a 50-goal season

Alex Godynyuk, 21, a fringe NHLer who had played 49 games before the trade

Michel Petit, 27, a depth defenseman with some offensive skill

Craig Berube, 26, a physical forward known best for his pugilism

Jeff Reese, 25, a backup goalie

Within 24 hours, families huddled around the sports page of the Calgary papers to find out what the Flames got back for Gilmour. Parents and children alike exclaimed that they’d never heard of any of the players acquired by Calgary. Many wondered why Risebrough didn’t just let Gilmour sit out and shop around for a better deal rather than immediately make a knee-jerk trade.

Confusion and frustration abounded, and were compounded over the subsequent seasons as the five assets acquired from Toronto disappeared into the ether without being converted into anything else. In a tough situation (a holdout), Al Coates was able to convert Joe Nieuwendyk into Dallas’s top prospect (Jarome Iginla) and a solid depth forward (Corey Millen) and that foresight allowed the Flames to make subsequent moves.

The lasting legacy of the Gilmour trade on the Calgary side was Jeff Reese’s three-assist game against San Jose in 1993 and very little else.





