Canadiens Mailbag: Could Stamkos reunite with St. Louis?

MONTREAL — There were 80 questions that came in for this mailbag, and 14 of them were about the upcoming draft.

I get it, people want to know who the Montreal Canadiens are targeting, whether or not they’ll move up or down the order from where they’re positioned with two picks in the first round, and whether or not they’d take a player at fifth overall that your favourite prognosticator would deem to be "a reach."

But if I’m disappointing all of them by saying I don’t know, so be it. Because when it comes to the draft, there’s a wide chasm between what I think I know and what those participating in it actually do. Those participating guard their information tighter than gold at Fort Knox.

Here’s what I know, for sure: The Canadiens don't make decisions by watching a 10-minute highlight reel of your favourite prospect, or by reading what some of the great draft specialists write on your website of choice. Their decisions are based on years of evaluating a prospect’s evolution, on data, on the combine, on psych evaluations, on conversations with people only they would have access to, on the player’s entire package and not just his raw-skill level, and they’re hotly contested internally before they’re made.

You want my opinions and I’ll offer them, along with the caveat that no matter how much information I’m able to unearth, I can never get deep enough into that process to put out predictions I would stand by with any degree of certainty.

Also, there’s a lot of disinformation that flows at this time, which makes going out on a limb an even more dangerous proposition.

Still…

On moving fifth overall: I don’t think the Canadiens could even say whether or not they would before seeing how the draft is playing out in front of them, so how could I? I just know that trading up from this position is practically unheard of nowadays, and I can’t even imagine what it would take for them to consider trading down. I would suggest it’s most probable they’ll be picking fifth.

On trading Winnipeg’s pick: That seems possible, if not probable. But I would think it would have to be packaged with other assets to net the Canadiens a player that can help them both now and moving forward or get them into a higher position in the order.

On whom they’re targeting if they stay at five: I would think Ivan Demidov would be really appealing to them, but I would also have a hard time believing he’ll be available at five. Again, just my opinion.

On Cayden Lindstrom: I don’t know how the Canadiens — or any other team — feel about the injury issues he went through, but it does strike me as concerning that an 18-year-old would already have back problems. If they’re concerned, perhaps they won’t be after the combine.

On late-risers Tij Iginla and Beckett Sennecke: I’d have to think that if the Canadiens were willing to pick them above where the prognosticators have them, it’s because they not only believe either one is the best player available at five but also believe that teams directly below them see them the same way. But hey, we can all sit back from our couches and call it a reach…

On the top defencemen available, particularly the right-handers: If either of them is available at five and the Canadiens think they’re the best player available, I don’t think they’re so deep at the position that they should absolutely ignore them and just pick a forward.

I have one more opinion on the subject: When Canadiens general manager Kent Hughes spoke after the draft lottery, he said the scouting staff was “very confident that we’ll be able to draft a very good player at fifth overall.” Based on everything I’ve seen and read — and on conversations I’ve had with people far more knowledgeable on the subject — I have no reason to doubt that.

I’m as eager as anyone to see how it plays out.

Now, on to the mail…

In theory, this is the earliest possible time signing a big-ticket UFA would sync up with the maturation of the Canadiens’ core, so I understand why the question is being asked.

Jumping ahead to 2025-26 and looking at the core: Nick Suzuki will be 26, Cole Caufield, Kirby Dach and Alex Newhook will be turning 25 by mid-season, and even though Juraj Slafkovsky, Kaiden Guhle, David Reinbacher, Logan Mailloux and Lane Huston will all be 24 or under throughout the campaign, they’ll have probably gained just enough experience between them in the NHL to at least help crack the Canadiens’ contention window ajar.

But spending top dollar and giving max term to an unrestricted free agent before that window is wide open wouldn’t enable the Canadiens to maximize the value of that player. They’d potentially be burning the first year or two of that deal without having a realistic chance of winning the Stanley Cup, and that could cost a lot more than just dollars and cents.

It could also end up burning opportunities to add pieces that would tip the Canadiens over the edge in years in which they’d actually be expected to contend, which would be anything but optimal.

I do understand, though, that turning away from one of the top dogs wanting to be in Montreal over any other city come 2025 is a risky proposition. Especially if signing one helps attract other talent to the market.

I also know that if that type of player is willing to come, his experience will help the team be better positioned to consistently compete for the Cup over the next three or four years.

That can be palatable, especially if that player is Leon Draisaitl or Mikko Rantanen (the best free agents potentially available in the summer of 2025).

I don’t think the Canadiens could fully ignore the opportunity to add either one, if they really, truly want to be in Montreal.

But it’s almost as hard to imagine that being the case as it is to imagine the Canadiens, as currently constituted, turning completely in their direction.

Rantanen will be 29 on Oct. 29, 2025 and Draisaitl turns 30 two days prior. That means they’d each be starting their next contracts closer to the arc of the aging curve than typical big-ticket free agents would be (at 27 going on 28).

Knowing that, signing them for what it will cost to sign them is a bigger gamble.

If the Canadiens wanted to take it, they’d have to make some major moves this summer to become more competitive and, therefore, more appealing to their target.

But even if I’m sure they want to make major moves this summer regardless, there are no guarantees they can make enough of them to realistically position themselves to be among the biggest players in free agency in 2025. And even if they can, it’s a hard scenario to envision for many reasons.

The main one, as I already pointed out, is that the earliest possible time the Canadiens’ core might be just mature enough to enable such risk-taking would be the 2025-26 season. And that might even be stretching it when you consider that Mailloux, Hutson and Reinbacher currently only have three games of NHL experience between them.

Even if each of them plays 82 games next season, a lot would have to go right for a big swing in free agency to make sense for the Canadiens in 2025. And just about everything would have to go right on top of that for the best free agents to consider Montreal as their top choice at that point.

Not really.

But I don’t think he’ll be a realistic option for any team, aside from the Tampa Bay Lightning.

Stamkos wants to retire as a member of that team, and they want to give him a chance to do that. I still think that’s the only realistic scenario at the moment.

But if things were to break down between Stamkos and the Lightning, I would say the connection to Martin St. Louis would be one of the only things that might have Stamkos even consider signing in Montreal.

Being guaranteed a spot next to Suzuki or Dach could help, too.

I just don’t think those factors would be enough to mitigate the reality that other teams out there would immediately give Stamkos a much better chance of winning than the Canadiens could. He’s 34 years old and wants as many kicks at the can as possible. He would be giving up one or two of them right off the hop in Montreal and doing so at an age where he can still be an effective scorer.

Hey, I think the Canadiens would be interested, especially since his next deal wouldn’t be anywhere near as prohibitive to them as the types of deals younger stars like Rantanen and Draisaitl will sign in 2025.

But even the Canadiens (with St. Louis on the bench and Vincent Lecavalier in the front office) probably don’t see it as realistic.

Not to walk that back but I would definitely like to provide a bit of context here. We were specifically asked which free agents we would target in 2025, and I was on the spot looking at the list and thinking about who would be most appealing in the second tier.

Bennett’s name immediately came to mind because I think, in terms of value, he’d be delivering when it matters most and doing so at a number that’s far more digestible than what you see in the first tier.

I’m just not sure the Canadiens are there yet — in case you couldn’t tell from my extensive answer to the first question in this mailbag — and I’m doubtful they will be if/when Bennett makes it to market. And jumping the market to get him now, when he’s already 27, probably doesn’t necessarily line up either.

Not that I’d consider it a bad move.

Bennett’s name was front of mind as the type of player I would target for any team diving into the free-agent pool. If I were leading one and was going jump into those waters, I would want it to be with a player like him, who I know will keep me floating when the tide gets higher.

You overpay in free agency no matter what. I’d rather do it for a player who costs way less than the top dogs but produces and contributes almost as much while also delivering in many other ways in the playoffs.

I did get a kick out of some people reacting to the 30-second clip of me mentioning Bennett, presumably shaking their fists at me and saying, "The Canadiens need talent," as if I was suggesting Bennett would be the only player the Canadiens could add over the next year. 

Can you wrap your head around the idea that it’s organically going to get better with better players coming and the roster getting deeper? Because I think that’s the answer.

This may be cross-current, given that the Canadiens finished 27th on the power play and 24th on the penalty kill, but I do believe they have coaches who can help them produce the results everyone wants to see.

If you zoom in, you’ll see the Canadiens ran the ninth-best power play in the league over the 27 games they played from Dec. 11 to Feb. 20, which isn’t a small sample. They also ran the 10th-best penalty kill over the final 40 games of the season.

While the players deserve a lot of credit for both those things, you can’t ignore the influence the coaches had on those outcomes while simultaneously blaming them for all that went wrong when they were less successful.

On the power play, St. Louis and Alex Burrows were deprived of Dach for all but one game of the season and had no stock to build a respectable second unit. But they still set things up in a way that made the Canadiens extremely threatening. On the penalty kill, St. Louis and Stephane Robidas weren’t exactly dealing with a full deck, either, but the changes they made to the structure began to bear real fruit once the players adjusted to them.

Give these coaches a full slate at both ends of the ice and special teams are going to get a significant bump. On the power play, Dach, Hutson, Mailloux and Joshua Roy are just some of the players who can help the Canadiens improve. And the penalty kill should also be bolstered by the improved depth at the bottom end of the team.

I absolutely do.

But Slafkovsky doesn’t need that designation to be considered a leader. I think he’s already shown he’s a natural leader — both in Montreal and in international competition for Slovakia — and the qualities that make him so are only going to take up more space as he grows.

You look at Slafkovsky’s early submission to the process of rounding out his game and his mentality of not putting personal goals ahead of the team’s goals, and you see a player who’s mature beyond his age. Coupling that with his determination to make a difference in every critical situation — whether by blocking a big shot or taking one to win a game — it’s easy to see why the Canadiens chose him first overall in 2022.

As for my own expectations of Slafkovsky’s progression this upcoming season, that's hard to quantify right now.

I don’t want to say he can’t be a 70-point player, because he was exactly that over the second half of the season when he produced 35 points in 41 games. It’s just that, like GM Kent Hughes said at his end-of-season press conference, I could see him levelling off a bit before taking another big step forward.

That would only be normal for a 20-year-old player, even one with the size and skill Slafkovsky possesses.

But I also wouldn’t put it past Slafkovsky to be even more productive next season than he was through the second half of last year.

I know that’s a wishy-washy answer, but perhaps I can give a more precise one after camp breaks in the fall.

One thing I won’t hesitate to say is this: I believe Slakfovsky is well on his way to becoming a bona fide top-line winger and I don’t think it’s beyond his massive reach to develop into one of the best wingers in the league.

I certainly don’t think he’ll be worse.

As for what I expect, my answer is a little complicated because, while it may be a grave disappointment to some if Anderson can’t at least get back to being a 20-goal scorer, I don’t even think that’s what’s of utmost importance if he’s going to contribute to Montreal’s success next season.

I know, that’s not a good thing to be saying about a player making $5.5 million on the cap and $7 million in actual salary, but I think Anderson can really help the Canadiens be a better team starting from a third-line position and only playing at even strength. And I think he’ll be primed to do exactly that if they’re able to add a legitimate top-six forward above him via trade this summer.

He'd be part of an expensive but strong bottom six, with players like Brendan Gallagher ($6.5 million), Christian Dvorak ($4.45 million) and Joel Armia ($3.4 million) also filling roles (if none of them are traded this summer). That’s where I think Anderson could redeem some of the value lost by not panning out as a top-six forward.

It's in starting there that Anderson could build up some confidence. He would see fewer premium matchups and use his speed, physicality and scoring ability to help the Canadiens win the depth game.

If Anderson is successful in that, he at least becomes a viable option to fill in when a top-six player is injured or slumping. I see all of that as the path to a bounce back for him.

If it comes with at least 20 goals, that’s a bonus.

I can’t say with any certainty what those contracts will look like, but I think the Canadiens will want to get them done this summer once they can officially be negotiated post-July 1.

I think Guhle will be looking at the six-year, $27.6-million contract Alex Vlasic signed with Chicago a month ago as a starting point for his own contract. If something similar is on the table for him this summer, perhaps he’d lock in.

He could also wait, as is his right, to see if he can do better with one more season under his belt.

Would Slafkovsky wait if an eight-year deal resembling those signed by Suzuki and Caufield was put in front of him this summer? I truly wonder, because I think it would be very hard for him to turn away from that.

To be able to secure that before he even turns 21 would be a coup for him, in my opinion. And it’s hard to imagine the Canadiens being anything but thrilled if they could lock him in at that price right away.

I would give the edge to Dvorak, but there are no guarantees either player are in the opening-night lineup.

And that’s a good thing.

There’s going to be a healthy competition at each of their positions, which should only force both of them to really bring it to secure jobs.

Both players have much to prove.

The deal would have to be too lopsided in Montreal’s favour to say no, which makes it highly unlikely anyway.

The Canadiens might have an abundance of left-shot defencemen on their depth chart, but that doesn’t make trading the most complete one away a winning proposition. I think you’d be creating a hole to fill another hole, and that’s hardly advisable.

You’d also be doing it roughly 185 games before Guhle even reaches his potential. He’s 22, has 114 games of experience, he’s already proven he can play night-in, night-out against the best players in the world, and he still has a lot of room above him before he hits his ceiling.

I may be a bit more risk-averse than some GMs, but I don’t think any of them would look at a player like Guhle and think trading him ends up as a win.