Edited Jan. 11, 2020 at 5:43 a.m.
The Caps aren't giving the Leafs Radko Gudas for a 4th round pick.
Call up Djoos, Boyd, Sgarbossa, and Moulson. Let the new kids develop in Hershey. On the above team, pairs are probably Kempny-Siegenthaler as a very good shutdown pair, Djoos-Jensen for average puck movement, Kulikov-Seabrook/Ceci as a veteran third pair to keep things under control. That doesn't make them a contender, but it's not the worst in the league this year, even before other teams sell at the deadline. Goaltending is average. Forwards end up very, very bad, but also not quite the worst, before other teams sell.
The Caps already have 65 standings points, after 45 games. Last year the last place team finished with 64, after 82. The above team is not as bad as last year's post-deadline Senators. The above team could play on a 70 point pace the rest of the way. That leaves them in a wild card, so draft position shouldn't motivate any of these trades.
So overall the Caps probably don't do most of this? Even though it'd be a ton of picks in a deep draft and it could turn into a lot of good players for a long time.