I’m interested

Could be a nice return, but how does that trade help the Leafs now? They can't just have two holes in the top 6 and hope McMichael and Robertson or some other players can slot there.

Leafs would want Wilson+ probably and the Caps will say no.

That Cap Space Opens enough for Milano & or Rodrigues who slot into there like a glove, also if they want they can package Mcmichael for Chychrun or Kane with money left over to resign Kane if need be

Small thought here (sorry for being knit picky): I think your lines once Wilson gets back would be slightly different:

ovi kuzy wilson
brown strome nylander
mantha eller oshie
sheary dowd hathaway

Here, you have a "grinder" for every line. Wilson will get to pucks / win puck battles to allow Ovi and Kuzy to focus on offense. Brown to do the same for 2nd line. Oshie / Mantha to do the same for 3rd.

As a Caps fan, I would be interested as well - but unsure if Leafs would be since they are "win now" mode.

the lines make sense and for the leafs, i see them trading nylander often, including a post earlier saying what teams are interested in him. they need the cap space

Milano and Rodrigues aren't top 6 F even if they can play in the top 6, and assuming they can get Kane and resign him would be bold. Plus he would be 34, signing him at that age for 6Mx6 or 7.5Mx4 is probably not a smart move for a team that is top heavy.

Perhaps if they are able to work a secondary deal elsewhere like for Meier for example but unless a direct trade doesn't work the Leafs are still going to want players they can use as well from WSH. The Caps would also need to shed cap to make the trade if they want to remove guys off LTIR.

i left space for wilson to come back (send fjallby down) it would work for this year

What do the Leafs need cap space for? Their biggest needs are another top 6 player and top 4 RHD. This trade doesn't fill that need, just losing cap makes no sense since it's not like they can just find one of those types of players in free agency.

The reason why you see lots of Leafs fans trading Nylander it is either because they think he's soft or they are freeing up cap to try addressing a need, or both. So, you might see something like Wilson for Nylander 1 for 1 or Nylander for Chychrun, which would be terrible trades for the Leafs most likely.

While the value is fair and as a caps fan I would do it, don't think it really makes sense for either team. Unless the leafs can immediately turn around and use these futures for an upgrade (Meier? Chychrun?) this would leave a team with just as tight a window as the caps with Matthews' extensions with a gaping hole in the top 6. For the caps, it would take certainty that both Backstrom and Hagelin are truly done to even consider adding someone with Nylander's cap hit. Even then, this ACGM would leave them with a 21 man roster when Wilson returns which is not ideal. Too many things would have to change imo for anything close to this to come to pass