The 2027 Off-Season Could Be Filled With Blockbuster NHL Trades
Imagine an NHL off-season when superstars such as Edmonton Oilers center Connor McDavid and Toronto Maple Leafs center Auston Matthews are part of a series of blockbuster trades.
It won't be happening this year, but those moves could occur in the summer of 2027.
McDavid and Matthews will each have a year remaining on their contracts by July 1, 2027. That's also the earliest date that they can sign extensions.
However, if the Oilers and Maple Leafs fail to rebound from their disappointing 2025-26 campaigns, both superstars could opt to wait and see how the 2027-28 season unfolds before putting pen to paper.
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Meanwhile, the Ottawa Senators could face a similar situation with captain and left winger Brady Tkachuk. So could the Columbus Blue Jackets with defenseman and Norris Trophy winner Zach Werenski.
Both teams have struggled to make meaningful improvement.
The Senators finished only two points better this season than they did in 2024-25 and were swept from the opening round of the 2026 playoffs. As for the Blue Jackets, they narrowly missed the post-season for the second straight year.
Another season spinning their wheels could make Tkachuk and Werenski rethink their futures.
Meanwhile, with the Winnipeg Jets, there's reportedly "plenty of noise" regarding goaltender Connor Hellebuyck's future with the team.
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Jets goalie Connor Hellebuyck has resurfaced in the rumor mill. Meanwhile, there's no indication that the Maple Leafs have approached Morgan Rielly about a trade, and there's more Brendan Gallagher speculation.
So far, there's no indication that Hellebuyck wants out of Winnipeg or that the Jets are shopping him. However, he could change his mind if they fail to improve next season.
Unlike the others, Hellebuyck won't be UFA-eligible next summer. The three-time Vezina Trophy winner is signed through 2030-31 with an average annual value of $8.5 million.
However, Hellebuyck could follow the example of Detroit Red Wings center Dylan Larkin and request a trade, using his no-movement clause to determine his landing spots.
Of course, none of these scenarios could occur. Those five teams could play well enough next season to keep their superstars happy and willing to sign extensions.
However, one or two of them could decide by next summer that it's time to move on, which could shake up the NHL landscape for years.
If all of them do, it would be the most significant summer trade market in living memory.
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This story was originally published June 20, 2026 at 10:10 AM.