The Devils trade their 2 seconds this year for Boston/Colorado (lower) #1. Flip the first to Tor for Kasperi Kapanen. Other option is the two 2nds to Tor for Kap. Thoughts?
Toronto likely declines two 2nds for Kapanen. They probably figure that the worst case scenario is him signing an offer sheet which they can't match, but would likely be in the range that returns a 1st and 3rd (in 2020).
Ballpark for our 2nd/3rd rounders: NJD2 (35th), NSH2 (53rd), BOS2 (58th), ANA3 (69th), DAL3 (81st)
Some comparable trades to move up into the tail end of the first round in recent drafts:
2015:
Tampa trades #28 to NY Islanders for #33 and #72
Toronto trades #29 to Columbus for #34 and #68
2014:
Tampa trades #28 to NY Islanders for #35 and #57
2011:
Detroit trades #24 to Ottawa for #35 and #48
2010:
Chicago trades #30 to NY Islanders for #35 and #58
2009:
Detroit trades #29 to Tampa for #32 and #75
2008:
Anaheim trades #28 to Phoenix for #35 and #39
2007:
Washington trades #27 to San Jose for #41 and a future 2nd round pick
2006:
Detroit trades #29 Phoenix for #41 and #47
Probably not a coincidence Detroit traded down as they seem to like to do that (and probably Yzerman had a similar philosophy since he spent time in Detroit's front office before going to Tampa). With the amount of picks we have, trading up is a possibility but typically you don't see teams trade out until they're on the clock.
Doesn't make a ton of sense to trade down before you see who's there. I can think of it happening a couple times in 'recent' memory. Anaheim traded #12 for #17 and #28 before the 2008 Draft; Allegedly they were eyeing Erik Karlsson and thought they could still get him at #17 (Ottawa traded up and got him at #15). Columbus traded #16 and #77 for #26, #37, and #56. Then John Moore fell further than expected and they traded back up to #21 to get him at a cost of #26 and #37. I remember seeing video of Brian Burke at Toronto's table grumbling that Columbus' trades were a lot of work and didn't net them much versus had they just stayed and taken Moore with their original pick.