Brad Treliving’s first trade deadline as Toronto Maple Leafs general manager is going to be an interesting one to watch. It’s going to be the first Leafs deadline with someone other than Kyle Dubas at the helm since 2018. That year, the Leafs’ “big” trade deadline acquisition was none other than longtime Montreal Canadien Tomas Plekanec. Ironically enough, the Habs are involved in the premise of this article, too. 
The Toronto Maple Leafs were one of 15 teams with scouts in attendance for Tuesday’s Montreal Canadiens/Ottawa Senators game, sending a pair of their own to check in on their divisional rivals. Having scouts in attendance means virtually nothing on its own, but with these two teams specifically, it’s worth diving a little deeper into seeing as both are far removed from any hopes of making the playoffs. They’ll likely be selling some pieces off at the deadline, and while the Leafs shouldn’t be expected to have a massive deadline like they did last year, they should be among the teams checking in on these teams. 
<blockquote class="twitter-tweet" data-width="550" data-dnt="true">
Full house of scouts and reps at the Sens/Habs game tonight in Montreal: ANA, AZ, BOS (2), BUF, CBJ, DAL (3), FLA, NAS, NJ, SJ, TB (2), TOR (2), VAN, VGK, WPG (2)
&mdash; David Pagnotta (@TheFourthPeriod) <a href="https://twitter.com/TheFourthPeriod/status/1749938988067013096?ref_src=twsrc%5Etfw">January 23, 2024</a></blockquote>
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So, do the Canadiens and Senators have anyone the Leafs should be interested in? Let’s have a look at some players said scouts could have been watching on Tuesday. 
<h2>Jakob Chychrun </h2>
We might as well start with the big fish in this discussion. Chychrun has been linked to the Leafs for what feels like forever, going back to the first time the Arizona Coyotes explored trading him. You’ll always find pundits citing a top-4 defenceman as a need for Toronto, and it probably helps that he played minor hockey in Toronto. 
The Senators finally put an end to the nonstop speculation last season, swinging a deal involving a first-round pick and two second-rounders to acquire Chychrun from the Coyotes. He’s been a bright spot in another season of more of the same from the nation’s capital, with seven goals and 27 points in 44 games so far this year. Ottawa is dead last in the Eastern Conference despite the additions of players like Chychrun on the back end and Vladimir Tarasenko up front. 
It was <a href="https://theleafsnation.com/news/tln-rumour-recap-predators-chychruns-kings">reported</a> that the Leafs are one of six teams who have checked in on Chychrun. It makes sense; they desperately need some help on the puck-moving front from their back end, which they put out there with the failed offseason signing of John Klingberg, and between the production on paper and the age, Chychrun would be a nice fit in their top four. That said, I can’t see Ottawa taking any less than the three draft picks they forked over to get him in the first place, and since there’s seemingly not much interest in the two sides parting ways, his Leafs debut will probably have to wait. 
<h2>Sean Monahan </h2>
You’ll always hear the words “Leafs” and “defence” in the same conversation, but that doesn’t always mean defencemen specifically. Their bottom six currently doesn’t have much of an identity, and the lack of a true third-line centre who can be trusted in all situations is just as apparent as that of a top-four defenceman. Enter Sean Monahan.
The former Calgary Flames top-ten pick is having a nice bounceback season after the Flames essentially paid the Habs to take him. He was limited to only 25 games last season, but made the best of those games with 17 points, and he’s kept up the production this season with 32 points in 48 games. He starts in the defensive zone 61% of the time, the fourth-highest d-zone start rating of all Canadiens forwards, and eats up a little over a minute of penalty kill time per game. 
Monahan is going to be a hot commodity over the next month or so, seeing that he’s an unrestricted free agent and only makes $1.985 million against the cap. He would be a perfect addition in the way that Ryan O’Reilly was last season, given he could either centre a checking third line with some added offence, or he could slide into the top six and push John Tavares to the wing if the Leafs wanted to load it up. 
Daily Faceoff’s Frank Seravalli floated a first-round pick as the asking price for the Canadiens, and if that holds, I wouldn’t expect the Leafs to be the team that crosses the finish line here. They have too many holes that need addressing and realistically only one first-round pick to dangle. That said, if there’s another way to get the deal done, I’d be doing whatever I can to get Monahan out of Montreal. 
<h2>Mathieu Joseph</h2>
Either Joseph really wants to be traded, or he really doesn’t. Either way, he’s playing at a level that has both his own team and opposing teams tuned in. It’s funny to compare the situation now to where it was at the beginning of the season when the Senators were looking to trade him in order to sign Shane Pinto. 
Joseph, who will turn 27 in two weeks, has developed into a fine middle-six forward and has been another bright spot for the Senators. He has 22 points in 34 games on the season so far, and logs more penalty kill ice time than any Sens forward not named Parker Kelly. He’s making a little under three million annually for two more seasons after this one, and while his numbers are no doubt a little bit inflated due to the lack of depth the Senators have, he’s still proving he could be a difference maker in a team’s middle six. 
Here’s the question &#8211; is Joseph worth a first-round pick? He’s young, on a cheap contract, and he’s scoring at a roughly 65-point pace (although this likely won’t remain for the rest of the year). Having him under contract at that price would make dangling the first-round pick tempting, but I wouldn’t do it unless there’s a subsequent upgrade on the defensive corps to be made for a cheaper price. 
<h2>David Savard </h2>
The concept of David Savard is intriguing, which is why I’m including him here. He’s a penalty kill workhorse, has some offensive ability with 11 points in 25 games, and could give the Leafs a reliable partner for Morgan Rielly so that T.J. Brodie can be bumped down in the lineup. He’s also on a relatively cheap contract, making $3.5 million this year and next. 
On the flip side, he’s also 33 years old, and given his status from previous trade deadlines, I can’t imagine the Leafs would be the only team interested. Combine that with the Leafs being a divisional rival the Canadiens will eventually be competing against, I don’t know that they’d necessarily be in a rush to sell off assets to them, and certainly not for a discount. 
On paper, the fit between the Leafs and Savard is apparent, but there would probably be an unnecessary amount of roadblocks between the team and a possible deal. Sportsnet’s Eric Engels speculated in a recent mailbag that his value might be too intriguing for the Habs to ignore, and if there’s a long line of teams looking to make that deal, I’d imagine the Leafs look elsewhere.
<h2>The Verdict </h2>
Out of the four names on this list, I’m probably more interested in either of the forwards than the defencemen. Monahan would be a tough pull unless you can guarantee an extension after this season, at least if you’re giving up a first-round pick, but the price might be a little easier to stomach for someone like Joseph, who’s younger and has two years left on his contract after this season. 
If it was last season, I’d be encouraging the Leafs to fork over assets for these players, but since there are not all that many to go around, they’re probably best off going for the best value targets as opposed to the hottest names on the market. Still, the fact that Joseph and Savard at least have term on their deals could make them worth checking in on, but the divisional rival tax will probably enter the conversation at some point. There will be lots of decisions for Treliving and Co. to make over the next few weeks, and I don’t envy them having to make those decisions.

Brad Treliving’s first trade deadline as Toronto Maple Leafs general manager is going to be an interesting one to watch. It’s going to be the first Leafs deadline with someone other than Kyle Dubas at the helm since 2018. That year, the Leafs’ “big” trade deadline acquisition was none other than longtime Montreal Canadien Tomas Plekanec. Ironically enough, the Habs are involved in the premise of this article, too. 

The Toronto Maple Leafs were one of 15 teams with scouts in attendance for Tuesday’s Montreal Canadiens/Ottawa Senators game, sending a pair of their own to check in on their divisional rivals. Having scouts in attendance means virtually nothing on its own, but with these two teams specifically, it’s worth diving a little deeper into seeing as both are far removed from any hopes of making the playoffs. They’ll likely be selling some pieces off at the deadline, and while the Leafs shouldn’t be expected to have a massive deadline like they did last year, they should be among the teams checking in on these teams. 

https://twitter.com/TheFourthPeriod/status/1749938988067013096

So, do the Canadiens and Senators have anyone the Leafs should be interested in? Let’s have a look at some players said scouts could have been watching on Tuesday. 
<h2>Jakob Chychrun </h2>
We might as well start with the big fish in this discussion. Chychrun has been linked to the Leafs for what feels like forever, going back to the first time the Arizona Coyotes explored trading him. You’ll always find pundits citing a top-4 defenceman as a need for Toronto, and it probably helps that he played minor hockey in Toronto. 

The Senators finally put an end to the nonstop speculation last season, swinging a deal involving a first-round pick and two second-rounders to acquire Chychrun from the Coyotes. He’s been a bright spot in another season of more of the same from the nation’s capital, with seven goals and 27 points in 44 games so far this year. Ottawa is dead last in the Eastern Conference despite the additions of players like Chychrun on the back end and Vladimir Tarasenko up front. 

It was <a href="https://theleafsnation.com/news/tln-rumour-recap-predators-chychruns-kings">reported</a> that the Leafs are one of six teams who have checked in on Chychrun. It makes sense; they desperately need some help on the puck-moving front from their back end, which they put out there with the failed offseason signing of John Klingberg, and between the production on paper and the age, Chychrun would be a nice fit in their top four. That said, I can’t see Ottawa taking any less than the three draft picks they forked over to get him in the first place, and since there’s seemingly not much interest in the two sides parting ways, his Leafs debut will probably have to wait. 
<h2>Sean Monahan </h2>
You’ll always hear the words “Leafs” and “defence” in the same conversation, but that doesn’t always mean defencemen specifically. Their bottom six currently doesn’t have much of an identity, and the lack of a true third-line centre who can be trusted in all situations is just as apparent as that of a top-four defenceman. Enter Sean Monahan.

The former Calgary Flames top-ten pick is having a nice bounceback season after the Flames essentially paid the Habs to take him. He was limited to only 25 games last season, but made the best of those games with 17 points, and he’s kept up the production this season with 32 points in 48 games. He starts in the defensive zone 61% of the time, the fourth-highest d-zone start rating of all Canadiens forwards, and eats up a little over a minute of penalty kill time per game. 

Monahan is going to be a hot commodity over the next month or so, seeing that he’s an unrestricted free agent and only makes $1.985 million against the cap. He would be a perfect addition in the way that Ryan O’Reilly was last season, given he could either centre a checking third line with some added offence, or he could slide into the top six and push John Tavares to the wing if the Leafs wanted to load it up. 

Daily Faceoff’s Frank Seravalli floated a first-round pick as the asking price for the Canadiens, and if that holds, I wouldn’t expect the Leafs to be the team that crosses the finish line here. They have too many holes that need addressing and realistically only one first-round pick to dangle. That said, if there’s another way to get the deal done, I’d be doing whatever I can to get Monahan out of Montreal. 
<h2>Mathieu Joseph</h2>
Either Joseph really wants to be traded, or he really doesn’t. Either way, he’s playing at a level that has both his own team and opposing teams tuned in. It’s funny to compare the situation now to where it was at the beginning of the season when the Senators were looking to trade him in order to sign Shane Pinto. 

Joseph, who will turn 27 in two weeks, has developed into a fine middle-six forward and has been another bright spot for the Senators. He has 22 points in 34 games on the season so far, and logs more penalty kill ice time than any Sens forward not named Parker Kelly. He’s making a little under three million annually for two more seasons after this one, and while his numbers are no doubt a little bit inflated due to the lack of depth the Senators have, he’s still proving he could be a difference maker in a team’s middle six. 

Here’s the question - is Joseph worth a first-round pick? He’s young, on a cheap contract, and he’s scoring at a roughly 65-point pace (although this likely won’t remain for the rest of the year). Having him under contract at that price would make dangling the first-round pick tempting, but I wouldn’t do it unless there’s a subsequent upgrade on the defensive corps to be made for a cheaper price. 
<h2>David Savard </h2>
The concept of David Savard is intriguing, which is why I’m including him here. He’s a penalty kill workhorse, has some offensive ability with 11 points in 25 games, and could give the Leafs a reliable partner for Morgan Rielly so that T.J. Brodie can be bumped down in the lineup. He’s also on a relatively cheap contract, making $3.5 million this year and next. 

On the flip side, he’s also 33 years old, and given his status from previous trade deadlines, I can’t imagine the Leafs would be the only team interested. Combine that with the Leafs being a divisional rival the Canadiens will eventually be competing against, I don’t know that they’d necessarily be in a rush to sell off assets to them, and certainly not for a discount. 

On paper, the fit between the Leafs and Savard is apparent, but there would probably be an unnecessary amount of roadblocks between the team and a possible deal. Sportsnet’s Eric Engels speculated in a recent mailbag that his value might be too intriguing for the Habs to ignore, and if there’s a long line of teams looking to make that deal, I’d imagine the Leafs look elsewhere.
<h2>The Verdict </h2>
Out of the four names on this list, I’m probably more interested in either of the forwards than the defencemen. Monahan would be a tough pull unless you can guarantee an extension after this season, at least if you’re giving up a first-round pick, but the price might be a little easier to stomach for someone like Joseph, who’s younger and has two years left on his contract after this season. 

If it was last season, I’d be encouraging the Leafs to fork over assets for these players, but since there are not all that many to go around, they’re probably best off going for the best value targets as opposed to the hottest names on the market. Still, the fact that Joseph and Savard at least have term on their deals could make them worth checking in on, but the divisional rival tax will probably enter the conversation at some point. There will be lots of decisions for Treliving and Co. to make over the next few weeks, and I don’t envy them having to make those decisions.

Could the Leafs swing a trade with a divisional rival? Scouts watch Canadiens/Senators

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