Quick hit off the top - you have 4 retained contracts on here, and you can only retain on 3 players at a time. It's fine though because I don't think one of those guys gets traded, at all.
-This is an extreme overpay for Kane - his best comp, as
@Ab27 said, is Claude Giroux - a still-productive veteran winger with a full NMC controlling his destination, and Giroux got back a 1st/3rd/Owen Tippett. I could see him beating that package (because ringzzzz) but not by a ton, and certainly not by this much - the Rangers are giving up a 1st, a 2nd, and a 22 year old recent #2OA who's seemingly putting it together this season (he's tied his career high in points with 33 games left to play this year). Leschyshyn & Kjellberg are minimal value players, so take them out (unless Chicago wants them for some reason), and change Kakko to Vitali Kravstov and you might have a start. Kravstov fits the Tippett profile better - former mid/late lottery pick on his 2nd contract and not living up to the pedigree.
-Winnipeg is not going to trade an everyday lineup player if they're adding Jonathan Toews - buyers typically try to *add* depth, not swap it out, at the deadline. Winnipeg would be much more likely to send out the pick and a guy like Dmitri Kuzmin or Anton Johansson if you're looking for a younger D prospect - guys that are probably a couple years away at best. I'd assume that Vesalainen is minimal value to them at this point so if you want him, I'm sure they'll throw his rights in.
-McCabe is a good player but this is a ridiculous overpay in my eyes. Bouchard has had a little bit of a sophomore slump this year but has still put up very strong metrics based on his usage, and is only 23. Take him out and I'd say the value is fair - or if you want to turn the pair of 2nds into a 1st and have Chicago take on the reclamation project that is Pool Party, I think it still works. But Bouchard tilts this package way too heavily into Chicago's favor.
-Jack Johnson might be one of the worst every day defensemen in the league right now. He's got a grand total of 4 assist in 48 GP despite getting 20 minutes of TOI every night. "So what, he's a defensive defenseman", you say? Well, not quite - GSVA has him in literally the 6th percentile of defensemen in the NHL for defensive GSVA. Meaning, if you put him in a lineup of 20 NHL D, there's gonna be only 1 guy putting up worse defensive numbers (and, cherry on top, offensive GSVA literally has him 1st percentile - meaning he'd be the 20th guy in that line of 20 offensively.) I just can't see *any* team offering up any sort of positive asset for a guy having such a bad season.
-Speaking of bad offensive seasons, Athanasiou has a grand total of 10 goals in 47 GP and is almost as bad defensively as Jack Johnson. The Isles don't need retention, and don't need to shed Josh Bailey's cap hit, and honestly shouldn't be buying anyways - but certainly not spending a pair of 2nds and a useful 7th D on a guy who's been less productive than the ostensible cap dump they're sending out in this deal (Athanasiou: 16 pts in 47 GP; Bailey: 19 pts in 49 GP.)
-I can't see Domi getting back a 2023 1st, even with retention. His offensive numbers are bright and shiny, and someone will overpay on that alone, but the fact is he's a guy that you have to shelter in the playoffs (look at his TOI on Carolina last postseason) and spending a 1st on those guys is just bad asset management. I'm guessing a 3rd and a prospect, or tops, a 2nd for Domi fully retained at the deadline.
-Ottawa doesn't need to clear cap at the deadline since they're not going to be buyers; it doesn't make sense for them to give up multiple assets to shed Zaitsev's contract mid-season when they can afford him through the end of the year and have a potentially wider pool to send him out to (at hopefully a lower cost) this summer.