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The Habs made their first big seller trade earlier this week when they shipped Tyler Toffoli to Calgary for a 2022 first-round pick, a 2023 fifth-rounder, prospect Emil Heineman, and winger Tyler Pitlick.  Our writers provide their thoughts on the move.

Terry Costaris: My response here is just a few hours after this trade. I’m sure in the days ahead that we’ll find out why Montreal traded away Toffoli now rather than in the summer. He still has quite a bit of term still left in his great contract, so there was no rush to move him – or so it appears.

One thing is certain, Calgary is in no way a loser in this trade. Montreal? Time will tell.

The key to this deal is Heineman. He is a speedy six-foot-one-inch forward with strong offensive potential. At the junior level, he was superb. Right now, though, Heineman is becoming acclimated in terms of playing against men with limited ice time, which is impacting his numbers.

The first-round draft pick that was acquired is good and can turn great if Calgary somehow collapses this season and the Habs get their pick in next year’s draft which should be a bit better than 2023.

I am no fan of this year’s draft. I’ve written why in an upcoming piece. If this pick can be used to acquire a very good 20-22-year-old Nick Suzuki type player, then I’m all in. The more quality prospects that Montreal obtains, the better.

Personally, I’m hoping that this pick is used as currency in a package deal involving one of Montreal’s veterans for a high-end prospect.

All the other aspects of this trade are minor. Pitlick and the 5th hardly move the excitement needle.

I will definitely miss Tyler Toffoli but the future is not now but four to five years from today. By then, he will be far less an offensive force than he is right now. But I still have to ask, why move arguably Montreal’s best trading chip now rather than later? We should find out in the days ahead.

Allan Katz: The analysis of this trade seems to be drawing three easy responses:

1) The Flames gave away too many assets – this is the smallest reaction and is supposedly coming from Flame fans who value their players and draft picks probably too high.

2) It’s an even deal – this is the largest reaction and it’s based on the fact that both teams had different needs and both teams fulfilled their needs with this transaction.

3) The Flames got the better of the trade – not a large percentage but somewhat significant. There is an accepted truism about trades that whichever team got the best player/asset wins the trade. It’s not hard to find Toffoli as the best player/asset in this trade.

Bottom line, both teams could do well but most likely, probably based on the value of the players drafted, one team will do better.

There are three pieces that are not being covered by many that are worthy of at least a look.

1) Trade possibilities –Toffoli probably attracted interest from a dozen teams. There is a possibility that the Habs might use this draft pick to package something intriguing since the majority of teams are always interested in a first-round pick and will sometimes overpay for one. So as solid a trade piece Toffoli is, the draft pick will be seen, by more teams, as a solid value for any possible deal.

2) Cap Space – The Habs opened up some cap space in this move that might help facilitate other trades by paying part of the outgoing salary to help pave the way for a Price Trade, a Hoffman trade, or a Gallagher trade to name three examples. It’s that word many use in sports these days: Flexibility.

3) Pondering the Pitlick possibilities. Since the trade, there must be six or seven fans wondering, “What’s with the Pitlick monopoly?” On what planet does a team collect three Pitlicks by coincidence? I have examined this conundrum for many minutes and I have some theories: Theory 1) The Habs are trying to replicate the success of the Gretzky brothers, Wayne and Brett. The problem here is that the team has acquired three Brent Gretzkys and no Wayne. 2) They think as a group they might thrive. A problem here is that Tyler is 30 and on the downside of a very average career. Rhett (21) played poorly in the USHL but in his freshman year at Minnesota is putting up a lot of assists and in his last four games has three goals and four assists, so he’s still a prospect with some upside. Meanwhile, Rem, who is with Montreal and is scoring at a 20-goal pace for the second year in a row, is only 23 and just might be the real deal. So maybe the new regime believes the three together can make things fun during the next few difficult seasons.

There is one very important series of facts I uncovered while researching this opinion; Pitlick was spelled Pytlick in Poland. A number of them immigrated years ago to the American Midwest where they all became farmers. The word Pytlick meant bag. So, I can say with assurance that the Habs will not land up holding the bag in this trade, they will land up holding three bags … and all by design.

Brian La Rose: This feels like a fair trade in terms of value but for them to move Toffoli that quickly, I’d have been shooting for a bigger return, especially with his contract.  Something tells me a fair trade would have been there next month or in the offseason.

That’s what has me wondering a bit about Heineman.  For them to move this quickly on a Toffoli trade, I almost wonder if he was viewed as the top asset in the trade, not the secondary piece like we all seem to suspect.  Is he viewed by management as the top prospect that many fans thought the Canadiens could get in a Toffoli trade?  If they feel this way, then I get this a bit more from Montreal’s perspective.  I think for them, they feel like they made out a lot better than the general consensus on this move seems to be.

I have no issues with moving Toffoli – his deal was going to be over well before the Habs come out of this rebuild, even if it’s a quicker one like they seem to be suggesting it will be.  But did they maximize the return?  My head says they didn’t although they did get a fair one.

Kevin Leveille: Full disclosure, I’m writing this within minutes of finding out about the trade and my head and my heart are absolutely torn as I try to figure out how I feel about this. Starting with the heart, I’m not sure how much I like trading one of the few guys who said they wanted to stay as a first trade. Toffoli was on a sweetheart deal as shown by the fact that he’s Calgary’s eighth highest paid forward coming in. I feel like I’m missing some wow factor in the return by trading a player on a contract like that who wanted to play with the kids on the roster. Calgary had some good prospects to choose from who were ranked higher than Heineman, so I’m a little uneasy that the Habs didn’t hold out to try to sweeten that deal and I certainly hope Heineman makes me look like a fool for saying this.

Now the head. This is a great indication that management is thinking long-term and that the one-to-two-year reset isn’t on the table and I’m thankful for that. Getting the 1st rounder with no salary retained is a definite win, and while I wish someone else was first to go, seeing veterans depart was promised from the moment Bergevin was let go, aggressively sending a message to the league that the Habs are open for business is a good look too. The Habs definitely made the Flames pay to get their guy, and have themselves two projects (Heineman and the 1st rounder) that could eventually make us forget how quickly both Tyler and Cat became fan favourites around this team. I guess my overall read on this deal is cautious optimism, hoping for clearer wins as we near the trade deadline.

Peter Longo: Will this be one of the worst trades in Habs history? The only other trade that might be close is the Courtnall for Kordic trade in 1989. Although that one went the other way for Habs fans.

Toffoli is a proven top-six winger. His stats speak for themselves in terms of goals and points. But what you can’t read is that he is an extremely intelligent, high IQ hockey mind in the prime of his career. He’s responsible defensively, a proven team player, and a proven playoff Stanley Cup champion. Every NHL team wants him. On top of that, he’s on a very reasonable (perhaps even team-friendly) contract for this year and two more. Simply put, Toffoli is a unicorn. You can’t find wingers of his calibre available. The asking price for Toffoli should have been high including a top draft pick (top 10) or a high-end prospect already in the NHL, along with a reasonable draft pick. And the Habs were under no pressure to move Toffoli, so they could have waited until they got the best package. Unfortunately, none of this transpired and the return for Toffoli will likely amount to nothing.

Let’s break down the return using the following draft pick probabilities from Dobber:

• A 1st round pick (top ten protected): The odds of a first-round pick playing over 99 games in the NHL is ~37%. Less so if you remove top ten picks. The Flames currently sit 13th overall so the Habs would obtain the 20th pick.
• Heineman: 2020 2nd round pick, drafted 43rd overall, currently playing in Sweden. Odds of a second-round pick playing in 99 NHL games: 17%.
• A 5th round pick: Odds of playing over 99 games in the NHL less than 8%.
• Tyler Pitlick: a 30-year-old, injured UFA at season’s end, thrown in for salary cap reasons.

So, there you have it. Generously (ignoring the top ten draft pick removal) the Habs received a combined total of 62% chance of obtaining a player who will play over 99 games in the NHL. Virtually no chance of ever producing a player as good as Toffoli. Pretty bleak.

Here’s another way to look at it. In two years’ time, Toffoli will be approaching UFA status. Assuming at 31 he will still be playing good hockey, do you think the Flames can trade Toffoli for 1st and 5th round picks? Of course – it happens every year. So really, the Habs traded two years of Toffoli in his prime, for Heineman. Either this kid turns out to be good or Kent Hughes just made one of the worst trades in Habs history. Is it too late to ask for Bergevin back?

Ken MacLeod: I very much like the trade from a Canadiens perspective, but if you were looking to declare a winner, getting this season and two more of Toffoli at $4.25M must have the Calgary management team cracking open the vintage champagne.

Calgary’s offence has mostly come from its stellar top line all season, but adding a legitimate top-six winger who had a career year last season with 28 goals in 55 games gives them an extra scoring option that creates a more balanced offence. When his fine two-way game is taken into account along with his competitive nature and valuable Stanley Cup Final experience, both recent and early career, the 29-year-old Scarborough native is exactly what this hockey team needed to add to its lineup right now.

And while the Canadiens didn’t make out like gangbusters here, the return was a very good one that will help move along the necessary rebuild/reset/rewhatever that Jeff Gorton and Hughes have kicked off with this deal.

Calgary’s first-round pick this season could be anywhere from late teens to mid-20s, which should net the Habs an interesting prospect in what is widely regarded as a very good draft.

While the first-round pick is the main focus of the deal for Montreal, it appears Heineman, originally drafted 43rd overall in the second round of 2020 NHL Entry Draft by Florida before being moved to Calgary last season as part of the Sam Bennett trade, is someone the Canadiens have had their eye on for a while.

According to Björn Hellkvist, Heineman’s head coach at Leksands IF in the SEL, the offensive-minded winger with a great shot and decent size at 6’1” 185-lb. is developing well in Swedish’s top pro league and could be a valuable top-six forward for the Habs in two or three seasons time.

Paul MacLeod: I am conflicted by the Toffoli trade. On one hand, the team is terrible and it is going to take one to two years at the absolute minimum to build a squad that can be a perennial contender while they have salary cap issues and have to move some contracts. It makes perfect sense in this context to move a veteran who may be — or is even likely to be — in decline by the time team is ready to contend again. So, the move makes sense. The return: Heineman, a top ten protected 1st round pick and a 5th round pick is good and could be outstanding if the Canadiens hit on the pick(s) and Heineman reaches his projected ceiling. More likely, it turns out to be an even trade.

On the other hand, Toffoli chose to come to Montreal (when many UFA’s do not), was a great teammate, a reliable scorer, a team leader, wanted to stay in Montreal, and was signed to a team-friendly contract.

In short, I like the deal, believe it was necessary, but still would have liked to see Toffoli stay. Hopefully, Heineman and the draft picks will ease the pain in a few years.

Norm Szcyrek: It’s disappointing to know Toffoli won’t be around to help this team get them out of the bottom of the NHL. Tyler appears to always be happy to be in Montreal. His production last season was outstanding, and he was rebounding from an early-season injury that required surgery to correct.  The return from Calgary appears to be reasonable. On the surface, the Flames appear to “win” this trade since it helps them immediately. Toffoli’s salary for the next two seasons is very reasonable considering his scoring ability and how well he expects to fit into their lineup.  It will take at least a few seasons before we can tell if the players Montreal received paid off.

Dave Woodward: The results of this trade, from the Canadiens’ perspective, will probably depend on whether Heineman and the first-round pick make an impact with the Canadiens.   Before the trade, this pundit had never heard of Heineman, although some of the scouting reports that have since been reviewed are encouraging.  The (likely) late first-round pick represents an opportunity that hopefully this new regime can exploit.  The fifth-rounder is effectively a lottery ticket and Pitlick is a journeyman on an expiring contract who was thrown in for cap reasons.  If he is not dealt before the deadline, Pitlick may be signed in the offseason to serve as a placeholder during the rebuild.  However, given his age and career to date, Pitlick will not be part of the team the Canadiens are trying to build in the medium to long term.

The Flames know what they are getting in Toffoli, a proven goal scorer and a 200-foot player who can also be part of the power play and kill penalties, all at a reasonable cap hit for the rest of this season and another two years after that.  Is the package that the Canadiens received fair value?   That will depend on how Heineman and the first-round pick (and perhaps the fifth-rounder) develop, as with all trades involving futures and prospects.  We will not know the answer for at least three to five years.  Nonetheless, this type of trade is the “futures” type of deal that the Canadiens must undertake if they are going to rebuild.

Of course, I would have preferred to see Dustin Wolf, Connor Zary, or Jakob Pelletier coming over to the Canadiens.  I suspect that Calgary quite rightly refused those requests.  We shall see if the package the Habs received is sufficient in the fullness of time.

One thing is certain.  Even with Toffoli in the lineup for the next two years at a very reasonable cap hit, the Canadiens would be rebuilding.   By trading Toffoli, they lose a quality mentor for the younger players for two years (Toffoli probably would not extend after two years of a rebuild) and instead have opted for future assets.  This is the better option given where the team is at.