In 2015, the Jets brought the Stanley Cup playoffs back to Winnipeg. It was 19 years in the making, but it was all too brief: The Anaheim Ducks swept the Jets out of the first round.
After that series, Cheveldayoff sat down with owner Mark Chipman and laid out what he felt needed to be done for the Jets to contend for the Cup. They needed to get younger, and allow those players to make a multitude of mistakes. The growing pains needed to be palpable, with the knowledge that the franchise would eventually be better for it.
"It wasn't a hard sell for ownership," Cheveldayoff said.
Then came the tougher sell: to the players.
Over time, there was buy-in for the Jets' plans. Blake Wheeler and Bryan Little signed long-term deals. Getting Dustin Byfuglien, who was coveted as a potential UFA, to commit to five years was a coup, as he told the team, "I think we're on the cusp of something here." The Jets identified the players they wanted to build around, and jettisoned the rest. (Happy trails, Evander Kane. May all your track suits remain dry.)