Not even JFJ would make those trades.
Of course he wouldn't, he was a bad GM
But, for the sake of discussion:
*The Leafs want to clear cap space, well, those two trades drop about 19.75M off their obligations next season.
*The only name player we'd be giving up is Marner. Jones is his replacement, and with the savings we develop, both he and Rielly can be signed next season at a combined rate of 14M give or take a quarter mill. Divi it up as you wish, I think they are very comparable players and would roughly earn the same amount. YMMV. Moving forward with a D group led by Muzz, Brodie, Rielly and Jones is very appealing to me. As Muzz and Brodie age out/traded, Rielly and Jones are still below 30 with Sandin developing and hopefully the Marlies can provide 1/2 more in the next 2/3 years.
*I'd rather lose one of Fischer/Dermott/Hutch to Seattle for nothing than the current choice of Kerfoot/Dermott/Hutch, believing Kerfoot would be their choice.
*Gaining three draft picks, including a first round pick should help bolster our prospect cupboard, and this will be important if we wish to re-sign Matthews and Nylander.
*We haven't touched moved 9 out of our 10 top prospects (according to Wheeler's rankings in the Athletic). This is important if we hope to see some form of infusion onto the Leafs in the coming years to replace too expensive/aging players.
*Crouse, while not a sexy player, brings a strong degree of the physical (8th in hits for forwards the last two years, 5th the last 3 years), has averaged 21 points over the last 3 years (with a high of 15 goals two seasons ago) while playing 3rd line minutes and could well benefit from playing with a C like Tavares (a better C than he has ever played with) who has a history of improving the play of his wingers, he has also PKed. I do not expect him to be a 1st line PF, but I can see him improving and becoming a decent 2nd line player, contributing 15-20 G with Tavares and effectively wearing down D in the corners.
Essentially, the trades boil down to:
Marner, Kerfoot, Holl, Mikheyev, Liljegren, Hallander (19.672M combined)
for
Jones, Crouse, Fischer (7.933M combined) a 1st, 4th, 5th + 11.739M in cap space.
Currently, CapFriendly has the Leafs for next season with a 16 player roster signed and 10.855M projected cap space.
My suggestions would see the Leafs having a roster of 14 players signed and 22.594M projected cap space.