The idea is to get Ryan then buy him out. If the Leafs win their division in 2018-9 or make the semifinal, the first conditional pick is a 1st. If they miss the playoffs, it is a 3rd, otherwise it is a second. If Karlsson re-signs, the other conditional pick goes to Ottawa. So if we get the division and Karlsson re-signs, the senators would bet three firsts...

I understand taking on Ryan is a burden, but you have to actually offer up something of value for a hall of famer in his prime.

Scraps that wouldn't even get you a 2nd round pick, but you want Karlsson with it... ok

There's no way Nylander signs that deal, he's easily worth $3m more, and that's with a hometown discount. Also, Dorion laughs at you. You could remove the conditions and he'd still laugh at you. If you want Karlsson, you're going to have to trade one of the young stars.

HAHAHAHAHA

Leafs could not afford to buyout Ryan given this structure you presented. Let alone resign Karlsson, Matthews and Marner amongst others.

Then fast forward a year, Karlsson leaves as a UFA and the Senators get nothing, and are stuck with Ryan's contract. And Dorian likely gets fired...

But the Lightning would give a better package than this, even at the deadline. Granted, they don't have room to buyout Bobby Ryan, but neither would you when you have to re-sign everyone.

If the Senators want to attach Bobby Ryan to a trade, since none of the allegedly interested teams can afford to keep him, they're going to have to find a third team to whom to give picks/prospects for taking him, and that's coming directly out of the Senators' return. I'm not even sure that this offer would be enough for just the third team, though....

I don't see anyone giving up that many picks for a rental. Wasn't Sparks the top goalie in the AHL this past season? Now that I think about it, Screw the Senators. They can hit the bottom and see Colorado get that really great Draft pick...