Marc Bergevin retired from the NHL as a player and jumped right into a variety of roles with the Chicago Blackhawks, scouting before moving behind the bench as an assistant coach. Eventually, Bergevin became the Director of Player Personnel, before transitioning to the assistant general manager role.
Kevin Cheveldayoff never played in the NHL, but joined the Chicago Blackhawks as an assistant general manager in 2009. The Winnipeg Jets hired him away after firing Rick Dudley when the organization moved and went from being the Atlanta Thrashers to the Winnipeg Jets.
Both Bergevin and Chelvedayoff learned how the Blackhawks manage their team. Cheveldayoff's time with the organization was a lot shorter than Bergevin's, but he also has more practical experience as a GM, managing the Chicago Wolves in both the IHL and AHL. The result is an interesting blend of learning on the job and a lack of knowledge early on.
As someone who follows both teams closely, I'll attempt to answer which general manager has been more effective at addressing team needs, and helping improve his team's chances of winning.
Marc Bergevin has become a notorious trader in the NHL. His first trade was Erik Cole for Michael Ryder and a third-round pick. Cole had three years left on his contract at the time. Bergevin has made trades with the long and short-term vision of his team in mind. Off-loading both Rene Bourque's and Travis Moen's contracts for expiring deals; a major boon to the Canadiens' cap situation next year.
In comparison, Cheveldayoff has never traded an NHL player for another. If teams cower when Bergevin calls them, they must snicker when Cheveldayoff is on the other end of the phone. Cheveldayoff's reasoning for not making any trades is always "we had a lot of talks, but there was nothing that we liked." That is GM-speak for "I value my own players too much." To have lasted for four years as an NHL GM and have not made an NHL player-for-player trade is mind-boggling. However, Cheveldayoff acquired Michael Frolik through a trade for draft picks, so all is not lost... until Frolik walks in the summer.
Logic over Loyalty
This is a hard subject, because one seems incredibly loyal to his coach, while the other is beyond loyal to his players. Bergevin has traded or let go to free agency Brian Gionta, Josh Gorges, Erik Cole, Travis Moen, Daniel Briere, Raphael Diaz and many more.
Kevin Cheveldayoff has traded Alexei Ponikorovsky and, well, he has not really made any trades to free up roster spots for any young players. Already a young team, Winnipeg decided that solid AHL players like Carl Klingberg and Eric O'Dell were not ready for fourth line duty. Instead, Cheveldayoff signed players like Chris Thorburn and Mark Stuart to contracts that are too long with too much money attached to them. All of this would not be a major problem if Cheveldayoff made trades, but alas, pigs have not flown yet. The loyalty factor does not include coaches, but firing Claude Noel and hiring Paul Maurice has been the biggest reason for the Jets turnaround.
Free Agent Signings
This is probably the one area in which Cheveldayoff has Bergevin beat. The Jets GM made one of the best signings this offseason by signing Anaheim Ducks cast-off Mathieu Perreault to a contract that pays him $3 million per year. Although this does not excuse Randy Jones/Adam Pardy/Olli Jokinen etc.
Bergevin has dipped his toe in the free agent market with varying levels of success. In his first year as GM he signed Brandon Prust to an expensive four-year contract and added Francis Boullion for good measure. His second summer he decided to add the defensive disaster known as Douglas Murray. Bergevin showed he was learning though, and this past summer decided to sign Tom Gilbert to fill in the spot opened after he traded Josh Gorges to the Buffalo Sabres. Even though Gilbert has not played up to expectations, he still is an upgrade over Gorges for less money.
Neither general manager has a particularly stellar record at signing free agents, but both have shown improvements over their careers. Because Cheveldayoff has hit a home run with Perreault, he has a leg up on Bergevin, but the growth Bergevin showed with his signings this past summer is a good sign for the future.
Although both men worked for the Chicago Blackhawks as assistant general managers, the growth shown by Bergevin seems to be superior to that of Kevin Cheveldayoff. Bergevin's strength is his asset management, which is evident in his ability to turn bad contracts into short-term assets for the Canadiens.
The evolution shown by Bergevin is rather impressive growth curve since coming from Chicago in 2012. He has begun to move away from chasing toughness and has shown a penchant for chasing skill above all else. Sometimes it burns him, but he still hasn't signed Chris Thorburn to a three-year contract that carries a $1.2 million cap hit.