How about for the fun of it and a bored summer.
Chicago:
Patches 1/2 retained
One of our many prospect RD
Alzner
Montreal:
Chicago 1st (protected) 2019 or 2020
Beaudin
Schmaltz
Seabrook
We trade Petry from a 1st or 2nd + at the deadline or when Weber comes back.
The question to me is which RD prospect of our many RD prospects. I do think that CHI is a likely trade partner, especially if MON takes Seabrook's salary off their hands in the process.
That said, Seabrook is their #1 RD, even if, last year, he had similar offensive production (only six more points in 24 more games played) than Rutta, the 28 yr-old professional Czech player CHI found in a haystack last year, as they often do when juggling their Cap issues. Schmaltz is also already pencilled in as their #2C, with Anisimov relegated to a 3rd line role.
I seriously doubt that MON can land Schmaltz in a trade involving the 30-yr-old Pacioretty. Much less Schmaltz AND Beaudin.
A trade of Pacioretty for Beaudin is much likelier, but it only amounts to Pacioretty for a late first rounder, in the end (27th overall). I do believe that Pacioretty is worth more than that and a forward prospect would likely need to be included in the deal. Only, we should stop dreaming about landing CHI's #2C in the process.
I'm not a fan of including Anisimov in the deal coming back MON's way because, while he could be considered a lower end 2nd line C who should be good for 20 Gs and, at least, help out the Habs in the goal-scoring department, he's definitely not a long term solution in MON as a 30-yr old. However, I'm pretty sure CHI would like to get rid of their 3rd line C at 4.55M for another three years, even though it would weaken their depth at C in case of injuries.
A trade of Pacioretty (1/2 salary held back), DeLaRose and Byron (1/2 salary held back) would give CHI tools to take a real stab at the Cup, even if they parted with the undersized Schmaltz (5'11", 172 lbs). That would leave their C-line as Toews - Anisimov - Krüger/DeLaRose - DeLaRose/Krüger. That may seem a lot to give for Schmaltz -- and it is -- but looking at the Blackhawks' depth chart, Schmaltz's value is higher because of the lack of skilled offensive depth in the system and the ageing core of the team.
I still don't think that CHI gives up Schmaltz for Pacioretty and Byron at half their salary and DeLaRose, though.
More likely deal happening would be Pacioretty (1/2 salary) + DeLaRose for Beaudin, Anisimov and a 2nd rounder. Is that a great deal long term? Absolutely not. Short term, it also doesn't transform the Habs, but it does solidify somewhat the C-line, enabling Drouin to return to the wing in the process: Danault (taking heavier defensive assignments) - Anisimov - Peca/Evans - Evans/Peca. IMO, there is some value to having genuine Cs in the lineup and returning Drouin to the wing as we await the arrival of Poehling and Kotkaniemi in the NHL.
The three years left on Anisimov's contract make him an ideal stop gap to ease both Poehling and Kotkaniemi into the NHL. He's also a tradable asset in the last year of his contract at the deadline that should get you a 2nd rounder back, in the least, IMO.
Beaudin, however, IMO, is still just a project, with a lot to work on, as an undersized D, to become a player of impact at the NHL level. I'd rather MON try to land
Henri Jokiharju
In 120 total regular season games with Portland, he has 104 points. Not bad for a defensemen. He's also 6'1" and 180 some odd pounds.
Ironically, both Beaudin and Jokiharju are projected as a Thomas Kaberle type of D, but, for one. Jokiharju is a much better skater than Beaudin and a more complete D as it stands. He's also a larger framed D at 6'1" VS 5'11". Beaudin has a better shot, though, and while, at his age, he might still grow some, there are no guarantees (Jokiharju, for example, grew an inch from his draft year).
I'd do a larger trade to change the 2nd rounder into a 1st rounder and a 2nd rounder, though, freeing up more Cap space for CHI in the process:
Pacioretty (half salary) + deLaRose + Petry for Jokiharju, Anisimov, Seabrook and an unprotected 1st in 2019 or 2020 and a 2nd in the other year. In this trade, CHI saves (Anisimov's 4.55M + Seabrook's 6.875M) - (Pacioretty's 2.25M + DeLaRose's 900K + Petry's 5.5M) an extra 2.775M for the upcoming season. Plus, it gets out of a 6-year contract for the 33 yr-old Seabrook at 6.875M in return for a 3 yr contract at 5.5M with a younger Petry at 30 years of age.
It may sound like we are clogging up the right side of D with ageing veterans at high-priced contracts, but, IMO, it buys time to properly develop our younger Ds like Fleury, Brook and Jokiharju who can play at the AHL level and step up with more confidence in three years when the other youngsters at C are getting their legs at the NHL level.
Soon, or down the line, Montreal can likely still trade one or both of Weber and Seabrook. Weber still has good value across the league, IMO, especially once he has proven that he has returned to form from his latest injuries. For Seabrook, we can hold back some salary if need be (there will be enough cheaper youngsters on the roster to make this possible).
The return in Jokiharju, Anisimov (as a stop gap to help develop the youngsters in their proper positions) a 1st and a 2nd is worth the financial implications of taking on Seabrook and Anisimov's contracts, IMO.
Once Weber is back, A RD of Weber, Seabrook and Juulsen will be solid and help rear the better LDs from amongst our younger LDs currently vying for a spot on the team. Alzner can play a 3rd pairing role with Juulsen, IMO. The experiment with the two together in a 2nd pairing role was a success at the end of last year. Playing a third pairing role won't expose them as much against the opponents' better forwards and they should be even more productive this upcoming year.
MON can use both Weber and Seabrook for the two, three or four years to help develop depth at the LD position, gradually replacing them with young RDs that are pushing for a spot on the team.
Anisimov can help develop our wingers until our C prospects are ready to take over with young wingers in full progression.