{"id":674749,"date":"2026-09-30T01:45:12","date_gmt":"2026-09-30T01:45:12","guid":{"rendered":"https:\/\/www.rawchili.com\/nhl\/674749\/"},"modified":"2026-09-30T01:45:12","modified_gmt":"2026-09-30T01:45:12","slug":"insider-trading-toronto-maple-leafs-look-to-remain-aggressive","status":"publish","type":"post","link":"https:\/\/www.rawchili.com\/nhl\/674749\/","title":{"rendered":"Insider Trading: Toronto Maple Leafs look to remain aggressive"},"content":{"rendered":"

TSN\u2019s Hockey Insiders on the Maple Leafs continuing to seek upgrades, the Habs striking out on Kirill Marchenko<\/a>, the Jets looking ahead to the season, the Red Wings\/Simon Edvinsson<\/a>\/Dylan Larkin<\/a> situation, the latest on Nikita Kucherov<\/a>, and officials on improper equipment usage.<\/p>\n

JAMES DUTHIE: Opening night edition of Insider Trading. James Duthie and Darren Dreger in studio, Pierre LeBrun and Chris Johnston at the game – the Leafs and the Habs – doesn\u2019t seem fair, but whatever, we\u2019ll move on. <\/p>\n

The Leafs pull off the Kirill Marchenko<\/a> deal on the eve of the season. John Chayka, C.J., has overturned half of the roster and is maybe not quite done yet? <\/p>\n

CHRIS JOHNSTON: Yeah, that\u2019s definitely a fair description of what the Leafs\u2019 approach is, even in these early days of the season. They\u2019re calling it patiently aggressive, but anyone who\u2019s watched the last three months would not call anything patient that\u2019s happened from Chayka thus far. <\/p>\n

The Leafs feel even after giving up Matthew Knies<\/a>, who they viewed as their best young trade chip, that they still have other futures that they can move for \u2018help now\u2019 solutions. That includes the first-round pick of the Colorado Avalanche<\/a> and some young prospects. I think they\u2019ll be looking to upgrade even in these early days of the season. <\/p>\n

One area to keep an eye on is their defence. They did have to include Emil Andrae<\/a> in a reworked version of that Knies-Marchenko trade. So they do have perhaps an opening there for another addition at some point here in the future. <\/p>\n

PIERRE LeBRUN: And Chris, while the Leafs were on Marchenko the entire off-season in terms of trying to get him out of Columbus, I can assure you they were not the team that phoned Columbus the most often. That would be the Montreal Canadiens<\/a>.<\/p>\n

From the moment Marchenko announced he wanted out, Kent Hughes, the GM of the Canadians, had Don Waddell, his counterpart in Columbus, on speed dial. They really, really wanted him. The idea was that Marchenko wanted to play with Ivan Demidov<\/a> in Montreal, they share the same agent in Dan Milstein. <\/p>\n

I think the Canadians thought they actually could sign him to a contract that was going to pay him less than what Toronto is paying him now, $12.5 million. But it never aligned because the Habs didn\u2019t have the thing that Columbus needed: a player in his prime on a great contract like Knies.<\/p>\n

Not for a lack of trying, the Canadians tried to involve a third team with other ideas, trying to go get a player to appease Columbus, but they just couldn\u2019t do it. So what now for Montreal? They tried to trade for Knies at the deadline, they tried to trade for Marchenko. <\/p>\n

They will still be big-game hunting, I think, especially next summer where they have salary cap flexibility. Hey, if a guy like Connor McDavid<\/a> decides he wants out of Edmonton, I can assure you the Canadiens will be all over that. <\/p>\n

DUTHIE: You\u2019ve got to be careful, that becomes a Twitter headline right away. <\/p>\n

The trade that the entire league is waiting on, of course, is Connor Hellebuyck<\/a> and the stalemate with the Winnipeg Jets<\/a>, which seems like one of the most defining moments of the franchise, in recent history anyway. <\/p>\n

DARREN DREGER: I think that\u2019s fair. The outcome of this stalemate is actually twofold. You\u2019re talking about a franchise-changing move by the Jets when they find the right fit for Hellebuyck. <\/p>\n

This man has been the face of the franchise for a number of years now. And just as important in looking at the return is the message that is sent to the dressing room, to the team that they\u2019re not bracing for a rebuild here. <\/p>\n

In fact, it\u2019s quite the opposite. Help is on the way. So when you hear some of the stuff that we\u2019ve been talking about all along that Winnipeg is not looking for a futures driven trade primarily, that\u2019s the reason why. It\u2019s to make that the guys in the room know help is on the way. <\/p>\n

JOHNSTON: Another player waiting for his fresh start is Dylan Larkin<\/a> of the Detroit Red Wings<\/a>. <\/p>\n

What\u2019s different about his situation – he has been in training camp, albeit recovering from an injury. But at this point in time, I\u2019m told there\u2019s been no tangible progress made towards making a deal for Larkin. <\/p>\n

It appears as though the Red Wings are going to enter this year having to try to support him, try to have him involved in what they\u2019re doing and eventually move towards a trade. Larkin has recently expanded his list to a wider range of teams that he\u2019d consider a deal to. But at this point in time, it has not sparked any more conversation. <\/p>\n

The Red Wings have been playing catch up really all summer after removing Steve Yzerman in mid-July. Interim GM Shawn Horcoff is also currently negotiating with Simon Edvinsson<\/a>, a top-pairing defenceman for them last year. He\u2019s left the Red Wings after being in camp on a PTO, but because he didn\u2019t get a new contract done with the season starting, he\u2019s away. Well, that negotiation continues. I think they\u2019d like a long-term deal on the Edvinsson side of things. <\/p>\n

We\u2019ll see where this ends up falling, but the Red Wings have tons of cap space to make a signing, but so far they\u2019ve been reluctant to use it. <\/p>\n

DUTHIE: The story of the off-season, some crazy contracts awarded, mostly to young players, completely resetting the market over one summer. <\/p>\n

And then, Pierre, you go to Tampa, Nikita Kucherov<\/a> on an expiring contract, still without an extension. How big a story does that become? <\/p>\n

LeBRUN: Could you imagine if the defending Hart Trophy champion as NHL MVP was playing in a Canadian market and was entering the final year of his deal without an extension? What a gong show that would be. <\/p>\n

But by the way, that\u2019s why Kucherov loves playing in Tampa. People leave him alone there. He barely does any media and it\u2019s why he wants to stay. He has no intention of hitting the open market. It\u2019s just that the Lightning and his agent Dan Milstein haven\u2019t been able to find the sweet spot in terms of that extension. <\/p>\n

But having poked around on this file on this day, I can tell you there doesn\u2019t seem to be a red flag other than the fact he\u2019s not signed. In other words, everyone involved is confident this will eventually lead to an extension. There\u2019s no nerves being frayed right now that he\u2019s entering the year without one, and I think that\u2019s probably true. <\/p>\n

DUTHIE: Every new season that starts comes with the league cracking down on something and this year might be equipment? <\/p>\n

DREGER: Usage of equipment, yes. I can tell you that players, coaches, equipment managers, and trainers were all forced to watch a video of proper usage of equipment. Now we\u2019re talking about visors, we\u2019re talking about helmets, we\u2019re talking about an untucked sweater. <\/p>\n

Now here\u2019s Trevor Zegras<\/a> of the Philadelphia Flyers<\/a>. He was warned a couple of times in a preseason game before he was given a penalty for improper wearing of the sweater. It was tucked into his pants. <\/p>\n

So players will be warned. If they don\u2019t heed that warning, then they\u2019ll serve a penalty. <\/p>\n

DUTHIE: That will become a major story as soon as some prominent player in the last two minutes of a tied game gets called for a tucked-in sweater. <\/p>\n","protected":false},"excerpt":{"rendered":"TSN\u2019s Hockey Insiders on the Maple Leafs continuing to seek upgrades, the Habs striking out on Kirill Marchenko,…\n","protected":false},"author":2,"featured_media":674750,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[5121],"tags":[4759,32468,33363,65796,5,78,69111,33168,4,39224,71587,33549,32467,77,18,32441,5288],"class_list":["post-674749","post","type-post","status-publish","format-standard","has-post-thumbnail","category-winnipeg-jets","tag-apple-news","tag-connor-hellebuyck-sports-hockey-player-player-nhl-api-8476945","tag-detroit-red-wings-sports-hockey-team-team-nhl-api-17","tag-dylan-larkin-sports-hockey-player-player-nhl-api-8477946","tag-hockey","tag-jets","tag-kirill-marchenko-sports-hockey-player-player-nhl-api-8480893","tag-montreal-canadiens-sports-hockey-team-team-nhl-api-8","tag-nhl","tag-nikita-kucherov-sports-hockey-player-player-nhl-api-8476453","tag-simon-edvinsson-sports-hockey-player-player-nhl-api-8482762","tag-tampa-bay-lightning-sports-hockey-team-team-nhl-api-14","tag-toronto-maple-leafs-sports-hockey-team-team-nhl-api-10","tag-winnipeg","tag-winnipeg-jets","tag-winnipeg-jets-sports-hockey-team-team-nhl-api-52","tag-winnipegjets"],"share_on_mastodon":{"url":"","error":"Validation failed: Text character limit of 500 exceeded"},"_links":{"self":[{"href":"https:\/\/www.rawchili.com\/nhl\/wp-json\/wp\/v2\/posts\/674749","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.rawchili.com\/nhl\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.rawchili.com\/nhl\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/nhl\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/nhl\/wp-json\/wp\/v2\/comments?post=674749"}],"version-history":[{"count":0,"href":"https:\/\/www.rawchili.com\/nhl\/wp-json\/wp\/v2\/posts\/674749\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.rawchili.com\/nhl\/wp-json\/wp\/v2\/media\/674750"}],"wp:attachment":[{"href":"https:\/\/www.rawchili.com\/nhl\/wp-json\/wp\/v2\/media?parent=674749"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.rawchili.com\/nhl\/wp-json\/wp\/v2\/categories?post=674749"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.rawchili.com\/nhl\/wp-json\/wp\/v2\/tags?post=674749"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}