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I think there's this idea that value is linear, which just isn't true. Both the 1st rounder and Jankowski are so insignificant, not only to Monahan's value, but especially to Barkov's even higher value that they hardly matter in this trade. I wouldn't go from a 1C close to the top to a 1C close to the bottom (of 1C's) for almost anything. When you play Barkov you win the 1st-on-1st centre match-up which is happening 1/3rd of each game, roughly 5/6 times. With Monahan I'd argue you lose it 5/6 times. This value isn't made up by adding Jankowski's or late 1sts. I wouldn't, as Florida, trade Barkov for 2x Monahan, because the issue you start running into is having more good players, than better good players. If your 2C wins his matchup 9/10 times that's still a net loss considering you downgraded massively on 1C. Then there's the entire issue that 2x Monahan cost the same as 2x, not 1x, Barkov as well.
Point being, top, top tier players are basically only traded for other top, top tier players. For famous examples where that didn't happen, see Hall, Taylor for Larsson, Adam. The only other option being very good prospects/picks, and this is mostly done to fit team needs or for teams to align better to their "competitive cycles", for a trade along the same lines but with brain activity involved on both parts, see Ryan Johansen for Seth Jones.
Basically never have teams traded down in percieved skill, especially on their most important positions (1C, 1D, G) and won out. When they have, like in Brassard for Zibanejad and picks (I actually stated this was poor at the time, but we should all be careful with hindsight bias) it's in order to get younger etc. It wasn't the value the Rangers got back that won them the trade - that was entirely based on Zibanejad actually being/becoming the better player. The 2nd and 5th rounder or whatever was involved is entirely irrelevant.
So trades that were in the mould of this: Thornton for magic beans, Seguin for Smith/Eriksson and a couple of bodies, Kesler for Bonino+ (which was entirely in Anaheim's favor if we ignore contracts and injuries), Burns for Coyle and beans etc.
The one I found that worked out the other way was Jeff Carter for Voracek and a pick (#8) that turned out to be Couturier. I can't tell you that much about #8 in this draft, but I can tell you that the expected value for that pick is way below Sean Couturier.