I think you need to learn about the Leafs prospects and Carolina's.
JVR (60pt 1st line LW) + Bracco(Projected 2nd Line 50point, insane skater/passer) + 2nd rounder for Fleury (projected top 4, realisitcally a 4/5 guy on a good team)

Then you trade Dermott which is arguably the Leafs best defense prospect, already better than Fleury for an Overpaid RH defenseman. Plus a 2nd line centre (best suited for 3rd) but still averages 50 points.

Your Trades just have the Leafs over-paying in both cases. Sorry

Sage: Fleury considered NHL ready and as such a better prospect with more upside than Dermott! Having said that I do agree that sending JVR, Bracco and a 2nd is an overpayment, particularly as I believe JVR would agree to sign long term! Reduce the prospect and/or eliminate the pick! Bracco is at least 2 years out but should project as top 6! Barrie would be a good get, and as IMO Dermott would fall behind Fleury, and likely behind Borgman and Rosen on Leafs depth chart I would make that deal as is. Hate giving up the depth at centre we have with Bozak but simply forces Babcock's hand on Nylander unless they use Marleau! Would likely need to move Marincin to free up 23rd spot for back up cemter. Likely Aaltonen. Moves also enhance Leafs overall cap situation now and in future!

Fluery got 26 points in 69 games in the AHL as a 2014 1st rounder. Dermott got 24 points in 59 games in the AHL as a 2015 2nd rounder. I would say they are even if not Dermott is the better of the two.

Doug: I completely agree with TMLSage, Fleury isn't as highly touted as everyone makes him out to be. He really lacks all the criteria that would make him worth a package like this, let alone a package involving just possibly JVR or Bracco.
a) He's a left shot defenseman, and they aren't as highly valued as right shot defenders. Also the Leafs are so full on the left hand side it's scary.
b) He's an unproven prospect, with no NHL experience. He could be good, but he's not worth JVR if he could stumble in the transition from AHL to the NHL level.
c) He had a pretty solid first impression in the AHL, but compared to Dermott and Nielsen, it wasn't all that special - and also both of them did it two years younger than Fleury did.

Overall, Fleury could be really good, but Babcock likes his right to left pairings and Fleury would just overcrowd the left hand side even more than it already is. He would also slot in behind Dermott, Borgman and Nielsen (and more than likely Rosen) since all of the ones I just mentioned could very easily make the jump to the NHL if need be.

Also, regarding the post, Barrie is very overrated for a player who can really only play on the PP, and does a mostly rookie team that ranked 2nd in the NHL for PP% really need all that much help that comes in an overpaid form? I mean we already signed Marleau, so I think we hit the quota. Barrie is pretty terrible in his own zone and struggles often with consistency and because of that I think the Leafs should stay FAR FAR away from him. Rielly has the ability to be a great two way defender, and we already know Gardiner's offensive ability, so the Leafs should be targetting a more shutdown-type right handed defenseman like Pesce or Toronto native Tanev.

67: I really like Fleury from the standpoint of 2 way game! His advanced stats are sick, and while I really like Dermott (not so much Nielsen), both really struggled defensively this year with the Marlies! If Dermott makes it "he will be Gardiner"! Offensively moves the puck well, not a PP quarterback by any means and tends to really struggle in his own end and in front of the net! Prone to huge mistakes! I love the thought of Pesce and/Tanev, but there certainly isn't a deal that I see that makes sense for Vancouver without giving up a number of high draft picks, and Carolina wants the moon for Pesce! As light as Leafs are on the RD, I think the organization feels that Liljegren is not more than a year away, or else they wouldn't have signed him to send him back to Sweden and lose the contract space! He's likely to start with the Marlies but I wonder how long before they move him in to take Carricks spot! I think your thoughts on Barrie have some merit but consider what has gone on in Denver! If you could have had him a year ago, I don't think that you would have thought twice! It's like many posts on here thinking that Tavares has regressed! Same issue with Duchene! I also only see the Marleau contract as questionable if there isn't some sort of gentlemen's agreement that they can move it after the 2nd year, when it still has the $6.25 cap hit but only $1.2 still to be paid! (wink/wink deal) Maybe JVR and Bozak get to stay for the year, and I believe as constructed, we may have a top 9 lineup that will be tough to match but something tells me that they will use those assets to help balance out the defense and look to bring in a Dman still in ELC! Good post, solid opinions, just as always, different ways to look at things! By the way, if Dermott works out the way you think he will, that's a far better scenario for the Leafs, cap wise and in years of ELC!

Massive overpayment for Fleury. He's a prospect and certainly not any better than some of the other Leaf prospects. And just to trade 29 goal scorer JVR hurts the Leafs this season. In a TDL if done, JVR would get more than Fleury.
Barrie is right now overpaid at 5.5m for what he accomplishing on the ice with Avs,. Bozak is needed this year as centre for the Leafs. Next year it would 10 times better for the Leafs to have cap space, Dermot than 5.5m Barrie. 5.5m could be spend much better. Dermot started out well for the Marlies, then suffered a high ankle sprain. Didn't look that good till later in the season and playoffs (maybe the effects of the ankle sprain were over). I think he's an NHLer.