First, Montreal is not a rival. They are out of the playoffs this season, and Drouin is a UFA. Hardly a rivalry this season.

Holmberg should stay at centre. I don't see how Drouin is an improvement over at least three LWers the Leafs have, Bunting, Kerfoot, Engvall. No, Leafs spend their limited cap better elsewhere. In. what world is Drouin a "scoring winger" now?

If you can get him with double retention without giving up a picks higher than 4ths then sure. If not, then it's really not worth sending decent assets over to the rival for a player who has been underwhelming for so long.

And in what world is Järnkrok a second line winger?

While I agree with everything else you said, Montreal will always be a rival. Not in the sense that they are on the same level. They are both at very different point. There is a hatred there that has tons of history to back it up. It's not about this year or the next 5 years. It's about who is the better franchise

I dont think you've seen Drouin play the last few seasons.

He left the team during a cup run, plays no defense, his offense isn;t that good and he plays a lackadaisical way that constantly looks like hes dogging it out there.

5 pts in 16 games this year doesnt say it all, watching him on the ice he looks disinterested at best.

MTL would probably take that offer in a second.

Whoever plays in the Leafs bottom six has to be decent defensively. Drouin is the most opposite of that. Besides the fit, he's just really struggled these few years. It's insane to say, but giving even a 7th to add him is not worth it because the salary is too high. Better off moving a 4th or honestly even this package (which would be an overpay) for a player like Josh Levo.

I've been following hockey since 1960. Of course Leafs/Habs are rivals, but certainly not in making a trade of a UFA when the Habs are missing the playoffs and the Leafs are in. Habs should make the best deal they can...with any team. And actually how the playoff system is, it isn't just the division is a "rivalry, it's the whole conference. Teams aren't going to not trade trade with 15 just because they are in the same conference.

Habs fans are cool with any return for Drouin at this point. We're not gonna pay to dump him, but he's not in our plans past this season.

He's played well the past 3-4 games, but he's never had the compete level to match his skill and no one has been able to get that out of him. Very little chance that he figures it out before it's too late.

I am a Habs fan and I would not recommend any team give up anything other than a "problem player" in return for Jo.

Use the cap on someone else. 5 pts in 17 GP for an offensive forward is not worth FCs, much less a younger depth player and a 3rd. If you offered anywhere near this package, Montreal would accept in a heartbeat - Drouin has played a total of 122 games since the beginning of the 2019-20 season and while he's performed somewhat well in that time (15-48-63), I think the fact that he's missed almost exactly half of the last 4 years' worth of games (he's played 122 out of a possible 242 Habs games in that timeframe) is a flag so red you can see it from a few towns over. He's already missed significant time this year, and I just don't think giving up premium assets for a guy with that injury history is going to be worth it, especially when his $2.75M cap hit basically eats up your entire trade deadline budget.

Leafs can have him for free if they want...

Well do it, but we rather Villeneuvle instead of Abruzzese
But beggars can't be choosers.