It's not my team, but a couple old transactions from 2008 that I like to cite as cautionary tales:
Through a couple trades, Anaheim turned pick #12 into #17, #35, and #39. I wish I could recall where I read/heard it, but apparently their primary target was Erik Karlsson. They thought they could trade down and still get Karlsson while adding a couple picks to replenish their farm system.
Ottawa then traded up from #18 to #15 to snipe Karlsson. Anaheim ended up with Jake Gardiner, Nic Deschamps, and Eric O'Dell. If Anaheim had stayed put and taken Karlsson, some of the "smart" fans would have made fun of them for reaching. I can't help but wonder if Karlsson could have helped some of those 2010s Ducks squads get over the hump.
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Tampa was fresh off from drafting Steven Stamkos #1 and they wanted a young proven NHL defender to grow with him. They identified Andrej Meszaros who was RFA. Ottawa didn't have a ton of cap room, so they were vulnerable to an offer sheet. It sounded like Tampa and Meszaros were ready to go that route, but Tampa previously traded away its 2009 3rd rounder which was required as compensation.
With training camp looming, Ottawa and Tampa instead made a standard trade which included San Jose's 1st instead of Tampa's. With hindsight, if Tampa was willing to give up its 1st+2nd+3rd for Meszaros, I would have been insistent on getting Tampa's 1st which ended up being the Victor Hedman pick. Hedman+Karlsson would have been a fun combo.