NHL Trade Talk Recap: Avalanche, Canadiens & Oilers What If?

Today’s NHL Trade Talk Recap (August 29, 2026) has a little bit of everything: Cale Makar’s massive new contract and the cap headache it creates for the Colorado Avalanche. Some of the most painful trades in Canadiens history. And an imagined blockbuster idea that would send Mark Scheifele and Josh Morrissey to Edmonton.

Makar’s Huge Deal Creates a Big Cap Problem

Cale Makar is officially locked in with the Avalanche for the next eight years, earning a massive $20.4 million per season. Colorado got the deal done before the deadline, but that kind of money comes with a catch—the team will have only about $11.6 million in cap space when the extension kicks in.

Now comes the tricky part. Colorado still has several important players to sign, including Lehkonen, Wedgewood, and Roy, and they may have to make some serious decisions about Nelson and Toews. Makar is worth every penny, but building a deep team around that contract won’t be simple.

Cale Makar Cashes In: Avalanche Lock Up a Superstar, Inherit a Cap Crisis

Montreal’s Most Painful Trade Decisions

The Canadiens have made plenty of great moves over the years, but a few trades still make fans cringe. The biggest one is obviously Patrick Roy, who was sent to Colorado after the infamous 11–1 loss to Detroit. Roy went on to win two more Stanley Cups with the Avalanche, while Montreal got a return that never came close to matching his value.

Montreal fans have two other trades that still haunt them a bit: the ones involving Ryan McDonagh and Mikhail Sergachev. McDonagh and Sergachev are two other names that still make Canadiens fans cringe. McDonagh eventually became a steady top-pairing defenseman and won two Stanley Cups, while Sergachev developed into a champion and key NHL defenceman. On the flip side, Scott Gomez and Jonathan Drouin, the players Montreal got in return, just never quite lived up to the hype.

The Most Regretted Trades By The Montreal Canadiens

Would the Oilers Go All-In for Scheifele and Morrissey?

Here’s a wild scenario floating around where the Oilers pry both Mark Scheifele and Josh Morrissey away from Winnipeg. Scheifele slots in as another elite center behind McDavid and Draisaitl, while Morrissey brings some real puck-moving skill to Edmonton’s defence. If both pieces actually landed in Edmonton, this team’s lineup would be almost unfair to go up against.

The price tag on something like this would be brutal, though. Edmonton would probably have to part with Ryan Nugent-Hopkins, Jake Walman, top prospect Isaac Howard, another young player, and a stack of draft picks. Winnipeg walks away with a nice blend of NHL-ready help, future assets, and draft capital. But for Edmonton, this would mean going all-in on winning right now, no looking back.

Would You Do It? Oilers Land Scheifele and Morrissey in Blockbuster

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