it's very far fetched, but it could happen. Toronto would likely have to give up a lot, which they don't really have other than JVR, who I wouldn't trade.

However, it would be pretty cool having the "Nylander Twins." What do you guys think?

I think it would be nice but the Leafs really don't need to be trading away valuable pieces for another small skilled winger, already have Nylander Senior, Brown, Leipsic, and Marner, would be cool though

It is an interesting idea. We also have Pens 1st rounder that could be used to trade up. Were almost at that point where we have too many solids prospects!
Liepsic and Hyman are similar players- do we need both?

Also interesting to look at is our depth down the middle (especially if we get Stamkos). Stamkos, Nylander, kadri, Matthews, Bozak, Hyman, Gauthier. We clearly don't have room for them all
Were also stacked on LW (more so if we sign Jimmy Vesey): JVR, Timashov, Vesey, Lindberg, Leipsic, Leivo, Johnson

So a trade like our late 1st + 2 specs (maybe Hyman and Lindberg) could be a possibility for little Nylander and it wouldnt hurt the Leafs at all.

I like your thinking!

Would take a lot more then dealing a Hyman or Lindberg to get into the top 5-6.

Like what?

Kadri to ARI for the 7th

They just signed Kadri long term. Don't think hes moving

There's not too many recent examples of brothers playing together and the team being successful. Obviously the sedin's were successful individually but they never delivered the ultimate prize. One Cup Final and many years of dissapointment. Staal's/Schenn's/Granlund's...never know if it makes for an awkward dressing room dynamic, but the concept of uniting brother's on the same team rarely has that magical chemistry for the team. Alexander Nylander looks like a fine hockey player, but I wouldn't go out of my way to trade up for him just for family ties.

Montreal is the obvious solution here. They need top 6 forwards and JVR would be a perfect fit for their 2nd line. I don't see Bergevin wanting to trade out of the 1st round though, so Toronto would have to really want Nylander because they are probably adding Pitts 1st rounder to get it done.

It might be a stretch to have both Nylander brothers to play in Toronto. Dad is a coach with Mississauga juniors, so he might like his family nea by. Micheal and Alexander's mother is really great looking, so maybe she should stay in town too.