The perfect deadline in my eyes realistic kinda

Conditional pick: if the Flyers make it to the conference final and Jake Allen plays in 50% of the games, this pick turns into a 2024 2nd round pick (PHI or whichever one they don’t trade away if they make another move)

I know that Philly is not a team currently in the goalie market for Allen, but I feel that they could soon be. With the uncertainty of Carter Hart’s remainder of the season, Philly might be in the goalie market. Though there are other teams that might need someone a bit more than the Flyers, Philly might be one of the few teams willing to meet the asking price Montreal wants. I feel that a veteran netminder to pair with a young goalie in Ersson would be great down the stretch, and they can split starts and figure out a starter if the Flyers squeak into the playoffs. If this were to happen first before any other deals, it sends a message to the other GMs that Kent Hughes will truly wait for someone to offer what he wants, even if that means waiting for another team to have an injury/leave that affects them in net. Not sure if the pick would actually be conditional, but if you think it’s too much, imagine it as just a 3rd. Sandström is just coming over so Montreal has a goalie they can call up in the scenario that Monty or Primeau were to get hurt, and so Dobes doesn’t get rushed into the NHL. Sandström could otherwise stay on loan with Lehigh Valley in the AHL so that their goaltending nor Laval’s carousel get affected.

I know the market for Monahan is reportedly a 1st round pick or assets that equal that value. However, Kent Hughes isn’t just necessarily looking for picks, but he’s also looking for young talent. I know a defenseman might not be what people had planned since we have a great defense, but trust me, this will make sense soon. Colorado has had rumors of Byram being available for trade for a while, and Ryan Johansen hasn’t been the 2C I think some Avs fans were possibly expecting. He hasn’t been bad, but maybe not what was expected. With that being said, Colorado sends a young, valuable defenseman to Montreal along with Johansen to not only acquire a 2C and a shutdown defenseman that can log big minutes, but they don’t have to give up a draft pick, and they gain cap space. Seems like a win-win for both parties. Montreal sees in Johansen can bounce back for them possibly or they can flip him, and Byram will be used as an asset, as you will see.

This might seem like an overpay/underpay either way in the eyes of some people, but let me explain. Anaheim is set for the future at center, highlighted by McTavish, Carlsson and Gauthier. Though I’ve never been a big advocate for brining in Zegras, I feel like Montreal would do it. They flip Byram and Johansen (or I guess you can look at this as a 3-way deal) as well as sending Jordan Harris to Anaheim for Zegras and Vaakanainen. Vaakanainen is more of a throw-in for depth for the rest of the year, as the Ducks will have plenty of left-handed defenders after this deal. The Ducks bring in Johansen since they’ll likely deal Henrique for a pick, so Johansen can play a year or so for them and hopefully boost his value. If he doesn’t? It’s fine, they have plenty of cap space and it’s a worthy gamble. Similar concept as the risk Montreal took in bringing in Monahan. Byram can play a lot in Anaheim and get a great opportunity with more minutes he may never get in Colorado, and Harris can get good minutes too that he may not get ever in Montreal past this season. Overall, weird looking trade but I tried to fill everyone’s needs here, and I think that was done decently well.

Though Mailloux, Barron, and Reinbacher are coming up through the system, I feel like Montreal still needs a RHD with a good amount of NHL experience that can still take big minutes. “But wait, if that’s the case then why didn’t you keep Savard?” As much as I like David Savard, I feel like his value is as high as it’ll be at least for the rest of his career. Veteran defenders with high mileage have fallen off a bit in the past, so I believe Montreal will deal him and not risk his value falling. As for Murphy, he’s younger and is a guy I could see fitting into Montreal well. Trading a pick and a young forward who may never get a good opportunity in Montreal to a team in need of good young forwards depth seems like a good move for both sides. Montreal has enough picks and prospects to where they can trade away some higher picks.

Deal doesn’t have to be with Arizona, but I don’t think they’d mind making a smaller push at the deadline with how much of a surprise they’ve been this season. Retaining on Pearson is cheap, and we do need to use up that one last retention spot. Low-risk, high-reward move for Arizona. And for Montreal, another pick doesn’t hurt.

It’s either Pearson gets dealt retained, or Monahan would be retained. The only other option would be doing what they did last year and being a cap broker for another team (see Bonino 3-way deal to PIT 2023 trade deadline).