I think Shanahan will be focussed on acquiring 2nd rounders in what is expected to be a deep draft.
Winnik: 2nd rounder...A good playoff type player that teams want.
Santorelli: 2nd or 3rd rounder.
Lupul: 2nd rounder...His injury history is why he won't get us a first rounder
Franson: 2nd rounder...Rental type;Will be a UFA so teams will not offer a first rounder.
Bozak: 2nd rounder...Some team could use a decent third line center in the playoffs.
Gardiner: 2nd rounder...He's still unproven and his big contract will not return a first rounder.
JVR: First rounder...Leafs will probably keep him.
Kessel: First rounder + prospect
Dion: 2nd round pick..Leafs will have to eat a considerable portion of his contract.
Kadri: First rounder...Leafs will probably keep him.
Holland: 3rd rounder...Bottom 6 player can be useful to some team.
Komarov: 2nd rounder...Leafs will probably keep him.
Rielly: 2 first rounders (or a top 5 pick in the Draft + prospect)...Leafs most untouchable player.
Santorelli is worth (much) more than Winnik... switch their values (at least).
Bozak is worth more than a 2nd.
Franson is likely worth more than just a 2nd (low first or 2nd + prospect).
Phaneuf is DEFINITELY worth more than a 2nd.
I wouldn't trade JVR for a 1st round pick that isn't top 2 TBH.
Holland should easily fetch a 2nd +.
People overvalue picks at this time. How many 3rd round picks end up having a more successful career than Holland has so far (not to mention he's still developing).
I'll check a random year, 2002? and see how many players were better than him from the 3rd round.
Edit: 4 players played 400+ games: Gregory Campbell, Frans Nielsen, Matthew Lombardi, and Valerie Filpulla. So i'd say there was 2 better players than current Peter Holland (Nielsen and Filpulla). Still think trading Holland while he's young, cheap, and growing is a good idea? He's not even in his prime yet, but he's better than 28/30 3rd round selections from the 2002 draft. I'm assuming you could do this with most drafts too...