Kevin Cheveldayoff may swap the eighth pick or move Connor Hellebuyck to Buffalo, potentially securing two top-ten selections to aggressively accelerate the franchise’s championship timeline.

Friday night's NHL Draft may be anything but routine for the Winnipeg Jets as heading into the draft, a wave of reports has emerged suggesting that general manager Kevin Cheveldayoff could be one of the busiest men in the building. 

Multiple scenarios are potentially in play that could reshape the direction of the franchise in a significant way. The Jets currently hold the eighth overall pick, a selection that on its own represents a prime opportunity to add a top-tier prospect to the organization.

But the rumblings coming out of the league this week suggest Cheveldayoff may have bigger ambitions than simply sitting at eight and making a straightforward selection.

The first thread emerged Tuesday when Fourth Period insider Dave Pagnotta reported that the New York Rangers are actively looking to move up in the draft and that Winnipeg's eighth overall pick has drawn their interest.

That alone would represent a meaningful transaction, but the more significant development came Wednesday when Frank Seravalli added a layer that changes the entire scope of what this draft night could look like for the Jets.

Seravalli reported that Connor Hellebuyck could be moved, and that the Buffalo Sabres are potentially in the running to acquire the elite goaltender. The framework Seravalli outlined is particularly intriguing, with the Sabres potentially able to help facilitate a deal that would allow Winnipeg to move up to the fourth overall pick while also retaining their selection at eighth. 

Then on Thursday, Sportsnet's Elliotte Friedman added further confirmation that Winnipeg has been active in discussions surrounding the fourth overall pick, noting that the Jets and the Calgary Flames are not the only teams with eyes on Buffalo's selection, suggesting a competitive market is forming around one of the draft's most coveted spots.

Taken together, the reporting paints a picture of a Jets organization that is not content to simply stand pat. Moving up to fourth while keeping the eighth pick would give Winnipeg two selections in the top ten, a remarkable outcome that could accelerate the franchise's timeline in a meaningful way. 

The potential cost of Hellebuyck, one of the best goaltenders in the world, is steep, but for a team that has championship aspirations and a window it believes is open right now, the calculation may be worth it. Friday night in Winnipeg could be a very long and very eventful evening. All signs point to Kevin Cheveldayoff having his fingerprints on more than one major move before the night is over.

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