Ottawa says no

You're over the cap already, and if you want the Senators to take Marleau and give you Karlsson, you're going to have to offer a really good package, especially if you can't take Bobby Ryan. If you add in 1-2 top prospects, aand maybe another pick, I think that would be a bit more fair.

Wow, I don't even know where to start.

First of all, why trade for Richardson when he isn't even in your lineup. Also, you signed Gardiner to an extension (a ridiculous one at that), and you don't even have him in the lineup. You are 2M over the cap, which is okay, as there are some moves you could make, such as dealing Brown, which wouldn't be ideal, but would have to do. also, EK on the 2nd pair?

For the points above, you could say I am nitpicking a bit, but none the less, some poor moves and lack of attention to detail. This isn't my reasoning for the 1 star however.

Your trade proposal for EK is awful at best. The 1st and 2nd in 2019 is fine, and so is Sandin, but the main pieces of value just aren't there. Marleau is not going to Ottawa, that just isn't a fit, and certainly not what they want in return for EK. Also, why would they want Gardiner? They are rebuilding, and quite frankly he doesn't really fit the system over there, especially considering you have him as a rental (as you sign him as a FA). Leivo could be a trade piece, but again, very little value. So, insummary, A 1st, 2nd, Sandin and Leivo could be PART of a package for EK, but Marleau and Gardiner would not be. A piece of real value would have to go over, such as Liljegren, Dermott, Kapanen, etc. Even then, I don't know if Ottawa accepts, due to us not only being in the same division, but also one of (if not) their biggest rivals.

well i've had enough of capfriendly for one day

Terrible to say the least. Hyman is a very good top 9 forward who helps his teammates by getting the puck, he works and plays hard. The Karlsson traded is just bad. Thats not enough for EK annndddd if he’s being traded to a divisional rival, the Leafs would have to pay a premium. I’d stay off Karlsson and go after a defenceman like Tamev, Spuergeon, etc. As Washington and Pittsburgh proved, you dont need a superstar defenceman to win. You need players that make simple, smart decisions.

Thanks for the feedback. It's a tough one. Here's some of my reasoning. The fact that Karlsson is going to leave takes some of the leverage Ottawa carries. The package I sent gives a top 3 offensive defenseman for now, a top defensive prospect for the near future, some young forward depth, veteran Hall of Fame forward depth on his final year (which is almost nothing in real $), a 2019 first to replace the one giving for Brassard, and a 2020 second. That is quite the package for one player who is a glorified rental at the time of the trade.
If Bobby Ryan came back in the trade, it would take away from Ottawa's return, and the Leafs wouldn't be able to make the cap dollars work.
Hyman was traded because of his replaceable traits and more importantly his cap hit. Absorbing Karlsson's cap hit requires cheap roster supplementation, which is where Grundstrom came in.
Richardson was a cap dump really, his cap hit was able to be buried, but Hyman was obviously the better player. Arizona basically did the Leafs a favour while gaining a pick and a player to reach the cap FL.