This series features players the Calgary Flames drafted and—regrettably—moved on from too soon. Be prepared for pain, frustration, and anger as we delve into what could have been!
The series will consist of 10 players and five honourable mentions. The criteria for the players selected for this list were that they had a career of at least 500 National Hockey League games, the Flames moved on from the players in their mid-20s, and the players had a noteworthy career after leaving Calgary.
The top spot goes to Cory Stillman. Without further ado, let’s jump into it!
Why does Stillman make the list?
The Flames drafted Stillman in the first round of the 1992 NHL draft, sixth overall. Stillman played two years for the OHL’s Windsor Spitfires before the Flames drafted him, scoring a combined 60 goals and 191 points in just 117 games.
He moved to the Peterborough Petes for the 1992–93 season, where he scored 25 goals and 80 points en route to an OHL championship. The Petes would fall short of winning the Memorial Cup as the CHL’s top team that year, falling 4–2 to the hosting Sault Ste. Marie Greyhounds.
After an impressive junior career, Stillman was ready to turn pro. He spent most of his D+2 and D+3 seasons in the AHL with the Saint John Flames. During this time, he suited up for 142 games, scoring 63 goals and 164 points. Stillman wasted no time showing off his offensive talent, scoring 35 goals and 83 points as a rookie in 1993–94.
He made his NHL debut in the lockout-shortened 1994–95 season, putting up two assists through 10 games. He never looked back; Stillman spent most of the next six years with the Flames, scoring 109 goals and 235 points across 393 games. However, his 0.59 points per game would be the worst of any NHL team he suited up for.
Stillman went on to have an illustrious career, highlighted by Stanley Cup wins with the Tampa Bay Lightning in 2004 and the Carolina Hurricanes in 2006. He didn’t win any individual awards but was instrumental in the Hurricanes’ Cup win over the Edmonton Oilers, finishing second in playoff scoring behind teammate Eric Staal.
The offensive winger enjoyed a 16-year NHL career, playing 1,025 NHL games for six different teams. Over that span, he scored 278 goals on 2,079 shots—a 13.3 career shooting percentage—and 727 points. His point totals currently sit in the top 250 all-time, tied with David Pastrnak (for now), Mike Foligno, and Jason Pominville.
Stillman wasn’t a superstar by any stretch of the imagination, but a reliable secondary scorer. Points-wise, his best two NHL seasons coincided with his respective teams winning the Stanley Cup. That is no coincidence; he was a valuable contributor to those championship squads.
What did the Flames have to show for Stillman?
The Flames traded Stillman to the St. Louis Blues ahead of the 2001 trade deadline. They received Craig Conroy and a 2001 seventh-round pick (Dave Moss) in return.
Moss was a fine pick—actually quite an impressive pick in the seventh round—who enjoyed a 501-game NHL career as a depth scorer. He scored 20 goals once and 30 points twice, flirting with 40 points in 2008–09. That season would mark his career best: 20 goals and 39 points while averaging 13:36 time on ice. Moss, however, left the Flames as a free agent following the 2011–12 season.
The big piece of the trade coming to Calgary was Conroy. He received an icy welcome initially, having been traded for the Flames’ leading scorer and not showing much offensive promise himself. But being elevated to centre the Flames’ top line unlocked his offence. He ended up scoring 60 goals and 188 points through 237 games across parts of four seasons as a Flame. That’s more than he had done through 372 games across the first seven years of his career.
Conroy left the Flames as a free agent after their 2004 Stanley Cup loss to the Lightning, but a trade in 2007 saw him return to the Flames for his swan song. He would retire as a Flame in 2011 and join the organization in a management role. In the spring of 2023, Conroy was named as the Flames’ eighth general manager.
Summarizing how costly the Flames’ mistake was
Bringing Conroy to Calgary was one of the best things the organization has ever done. But it came at a high price. The Flames gave up one of their best players at the time for a late pick and a 29-year-old centre whose career-high in points was 43.
The Flames did well with the draft pick, and Conroy briefly more than made up for Stillman’s lost offence. But the Flames lost both Moss and Conroy for nothing and even spent more assets to bring Conroy back at age 35.
The Flames surely could have found a much better return in a Stillman trade had they waited a bit longer for his offensive game to emerge. There’s no doubt in my mind that they lost the trade, ultimately having nothing to show for it. However, it’s a trade I would make every time if it’s the only way to bring Conroy aboard.
Do you agree with our assessment of the Flames’ handling of Stillman? Let us know your thoughts!
Check out all of The Win Column’s posts from this series:
Main list: #10 Jonas Hoglund | #9 Robert Svehla | #8 Travis Moen | #7 Steve Begin | #6 Sam Bennett | #5 Dion Phaneuf | #4 Derek Morris | #3 Jarret Stoll | #2 Craig Anderson | #1 Cory Stillman
Honourable mentions: #5 Michael Nylander | #4 Jean-Sebastien Giguere | #3 Sean Monahan | #2 Marc Savard | #1 Martin St. Louis
Photo by Brett Holmes/Icon Sportswire
