IMO if the Leafs are going to give up futures for a dman this is the year to do it.
I get all of us are a little gunshy of trading away young talent due to past mistakes, but IMO Toronto is in a unique situation.
We have heard alot about how they're the first team to have to resign their whole core *before* a cup due to the rising cost of RFAs, but the flip side of that is they are going to have their core for the foreseeable future - not many significant costs coming after 2019-2020.
After the cap hurdle next year they will have Kadri, Rielly, Nylander, Tavares, (assuming they sign) Marner, and Matthews together for at least a few years before any need to be resigned.
Kadri and Rielly will be the first to expire from that group, and at Kadri's age they'll likely move on from him. It's likely they'll have Kapanen and Dermott signed as well.
As has been discussed here alot, the biggest benefit of holding onto futures is you keep your core surrounded with young talent on the cheap, until you either move out the core, or the previous mentioned talent for more cheap, talented depth.
However, IMO moving out talent from this year won't have a huge impact down the road. Toronto has a wealth of wing talent looking for opportunity and chances are one or two pan out. They have some decent looking d prospects as well, but an NHL D core that lacks depth and IMO a top pairing guy. Yes I am aware they have done well this year as a group.
They also have cap space this year, no space next year, and then mostly likely a bit of space in 2020-21.
IMO you roll the dice this year on a top pair dman only if you can pry someone with a package of futures - quantity for quality. You hope that the guys on the Marlies fill the holes of whoever is sent out, and hold onto your assets tight again starting next year. It's also interesting because they can keep both Gardiner and thier trade target for this years playoffs run, and then let Gardiner walk and use the money for their new acquisition.
Theyre going to have to give up one piece that we are all going to hate... I can't see Kapanen being moved anymore, so I think it's likely Dermott, Lil, or Sandin. The 1st from this year is gone, and most likely a 2nd with conditions for turning into another 1st with a finals appearance. Hopefully a guy like Brown still holds a little value (and we can shed his salary for next year while replacing his meagre production with a minimum salary player,) and a B level prospect. Does that get it done? Idk. Fans from both sides will say no and that they hate it, but personally I do it. Go for the cup this year with Gards. I don't think a 1.5 season blip is going to gut the team of their future depth, and could likely fill a huge whole during their biggest window.
Since this thread is about Sandin/Dermott...
Sandin/Dermott
2019 1st
2020 2nd (conditions for a 1st)
Brown
Prospect
For Pie and middle pick.
Flame away.