He was assistant general manager in Chicago and the Blackhawks were coming off a championship that came with consequences. They had to tear down what they had built.
In just over a week, the salary-cap-strapped Blackhawks traded Dustin Byfuglien, Ben Eager and Brent Sopel to the Atlanta Thrashers in one deal, Andrew Ladd in another, Colin Fraser to the Edmonton Oilers and Kris Versteeg to the Toronto Maple Leafs.
Fast forward to 2015, the Blackhawks have two more titles and Cheveldayoff, now the Winnipeg Jets' GM, and the rest of hockey can see the same storm brewing for Stan Bowman and Chicago. Confetti may still be strewn across the parade route, but changes are coming once again because of the cap.
"Considering the success we just finished off the season with and the excitement, it does feel a lot like 2010 where it's imminent and all of a sudden we kind of turn our outlook from the positive to the negative of everything," captain Jonathan Toews said. "Obviously not an enjoyable moment knowing that we might have to lose a few (players)."
This time it's likely to be forwards Patrick Sharp and Bryan Bickell, two of the Blackhawks who were on all three Cup teams. With Brandon Saad needing a new contract, there's probably no money for defenceman Johnny Oduya or centre Antoine Vermette either, and Brad Richards would have to take a discount to stay.
The 2015-16 Blackhawks will be much different and almost certainly younger. But after rebounding from the first cap catastrophe, Toews is confident Bowman and Co. can do it again.
"We always seem to keep that identity and that culture in our locker-room that we know what to expect from each other," Toews said Tuesday. "Obviously it's unfortunate the high that we just experienced winning the Stanley Cup, all of a sudden having to shift our focus from that to something that doesn't make us feel so good as far as losing teammates.
"It's an unfortunate part of the game, but I think everyone grows and moves on from it."
Ladd has rings from 2010 and the 2006 Carolina Hurricanes, but even he's a little jealous of the success the Blackhawks have had since trading him. Now Cheveldayoff's captain in Winnipeg, the 29 year old called Chicago the standard in the NHL right now.
"I think everyone, all the players, are jealous of the success that they've had," Ladd said. "I think the core guys there have done a phenomenal job of setting a good example for everyone that's come in. You have four Hall of Famers there. I don't think many teams can say that."
Around the core of likely Hall of Famers Toews, Patrick Kane, Marian Hossa and Duncan Keith there's Brent Seabrook, Sharp, Bickell, Niklas Hjalmarsson and goaltender Corey Crawford. Since 2010, Bowman has mixed in the likes of Michal Handzus, Oduya, Saad, Marcus Kruger, Andrew Shaw and others to keep the Blackhawks chugging along.
"You would have to say it's impressive because of what they've done in the salary-cap (era)," Cheveldayoff said. "To different extents (Bowman has) had to do different things like that. He pays attention to the deals that he's done and made some good moves."
The Blackhawks aren't just the envy of Ladd and his former teammates. Montreal Canadiens defenceman P.K. Subban admires the way they've drafted to stay on top.
"They've drafted very, very well," Subban said. "Sometimes it is luck, and picking a guy that maybe you don't think is going to be the player that everybody thinks he's going to be, and it turns out to be a steal, right? So that happens.
"You need some luck and some good bounces, and they've had that."
Just like 2010, rivals will be able to take advantage of the Blackhawks' depth. Fortunately for Chicago, there's plenty to spare.
"We can go through the list of players, but a lot of those guys would be first- or second-line players on most teams in the league," Subban said. "And some of those guys are on their third line. So there's no lack of depth on that hockey club."
If history is any indication, whatever of that is depleted this summer won't take long to get back.
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