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Flashback Friday: Looking at the Theo Fleury trade with the Avalanche
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Photo credit: Sergei Belski-USA TODAY Sports
Ryley Delaney
Feb 27, 2026, 21:00 ESTUpdated: Feb 27, 2026, 20:51 EST
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The National Hockey League trade deadline is just a week away.
At this point, it’s clear that the Calgary Flames will sell. Players like MacKenzie Weegar, Nazem Kadri, Blake Coleman, Zach Whitecloud, and Ryan Lomberg. The Flames are in a position where they need to tank for the future of the club, as they need a legitimate superstar forward. It’s been nearly 40 years since they last won the Stanley Cup, and they have to get out of the “mushy middle”, even if that’s by losing plenty of games over the next two or three seasons.
It was 27 years ago on Saturday that the Flames traded away the last remaining Stanley Cup champion, although netminder Mike Vernon joined the team again a couple of seasons later. On Feb. 28th, 1999, the Flames sent Theo Fleury and Chris Dingman to the Colorado Avalanche for Rene Corbet, Wade Belak, a 2000 second, and future considerations.
Fleury went on to score 10 goals and 24 points in 15 games with the Avalanche, as well as five goals and 17 points in what would be his last 18 playoff games. Joining the New York Rangers for the 1999-2000 season, he scored 15 goals and 64 points, but reached the 30-goal mark again in 2000-01, scoring 30 goals and 74 points in 62 games. 
In 2001-02, he scored 24 goals and 63 points, then joined the Chicago Blackhawks for the 2002-03 season where he scored 12 goals and 33 points. Fleury also won the gold medal with Team Canada at the 2002 Winter Olympics in Salt Lake City.
Of any player involved in the team, Dingman had the most team success, despite only playing 385 games with 15 goals and 34 points. Drafted 19th overall in the 1994 draft, he was a part of the Avalanche team that won the Stanley Cup in 2001, picking up four assists in 16 post-season games. 
He was traded to the Carolina Hurricanes shortly after, then traded to the Tampa Bay Lightning during the 2001-02 season. In 2004, he was a part of the Lightning roster that defeated the Flames in the Finals. That post-season, he had a goal and two assists in 23 games.
As for what the Flames received, Belak only played parts of two seasons with the Flames, picking up three assists in 72 games. Belak went on to have a lengthy career afterwards, mainly playing for the Toronto Maple Leafs from 2000-01 until 2007-08, then parts of two seasons with the Florida Panthers, then parts of three seasons with the Nashville Predators. He retired during the 2010-11 season, but tragically passed away in the summer of 2011.
Colbert played just 68 games with the Flames in 1998-99 and 1999-2000, scoring nine goals and 23 points. Around the 2000 trade deadline, the Flames sent him and Tyler Moss to the Penguins for Brad Werenka, with Colbert playing just 47 more NHL games before finishing his career in Germany.
The 2000 second-round pick was used to select Jarrett Stool, a centre who went on to find plenty of success in the playoffs, including two Stanley Cups with the Los Angeles Kings in the early 2010s. Unfortunately, the Flames couldn’t agree to terms with Stoll, and the trade they had set up with the Maple Leafs was denied because the fax was sent late. Two years later, the Edmonton Oilers drafted him in the second round.
So, this trade doesn’t look great for the Flames, as they traded away a productive player for two players who’d go on to play 119 combined games for the Flames, as well as a draft pick that essentially wasn’t used. Well, that is until you take a closer look at the “future considerations”, as that turned out to be Robyn Regehr. (The Flames were given a short list of Avalanche prospects to choose from, and selected Regehr.)
Born in Brazil and spending a part of his childhood in Indonesia, the left-shot defenceman was drafted 19th overall by the Avalanche in the 1998 draft. He made his NHL debut the following season, scoring five goals and 12 points. Over time, Regehr became an important end to the Flames’ back end, scoring two goals and nine points in 26 post-season games in 2004, which is the closest they’ve come to winning the Cup.
After the deep playoff run, Regehr set a career-high of six goals and 26 points, followed by two more seasons with 20 or more points. His tenure ended after the 2011-12 season, as the Flames traded him to the Buffalo Sabres with Aleš Kotalík for Paul Byron and Chris Butler, but we looked at that trade in a Throwback Thursday last year.
Regehr went on to win the Stanley Cup with the Stoll and the Kings in 2013-14, before retiring following the 2014-15 season.
Ryley Delaney is a Nation Network writer for FlamesNation, Oilersnation, and Blue Jays Nation. She can be followed on Twitter @Ryley__Delaney.
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