Junctures that hit my imagination and stuck in my memory from past winners:
2011: Teemu Selanne picked quite late, and of course, Pierre Turgeon and seventieslord's legendary defense of him as his 2nd line center. The Wayne Cashman pick.
2012: I don't remember any; I guess building a Big Three on defense was a bold strategy and it worked. Maybe Brind'Amour?
2013: Not trading up for Vézina and having him fell to me anyway, and getting Jimmy Thomson as my 3D with the saved pick.
2014: Succeeding in extracting all the value of Cowley and Drillon while covering for their weaknesses completely.
2015: Hard to pinpoint any exact decision, but the meta-decision to build a different kind of structure was very very bold.
2016: Picking Brett Hull when he already had Bathgate, than waiting long for his 1LW and 2LW, ultimately getting Krutov and Foyston.
2017: Trading Messier for an upcoming pick with Trottier still on board. Trading up for Geoffrion with no one left to replace him. Picking Brimsek to compensate lost value from bad trades. The Modano and Fredrickson picks. Trading up for Jamie Benn scooping jarek (he was so pissed!).
2018: Drafting two defensemen early (Park and Salming). Stamkos on the 2nd line.
2019: Likewise, drafting two defensemen so early, Kelly and Stevens, and then add Georges Boucher for a great Big Three.
All of this is totally subjective.
Interesting that TheDevilMadeMe won the first draft of the 2010's and the first draft of the 2020's. He also won in-between in 2014, and those feel like three very distinct eras.
ATD eras since the annual format:
2010-2011-2012-2013
2014-2015-2016-2017
2018-2019-2020
Those are subjective obviously, but the zeitgeist felt different. I think the ATD peaked in 2010-2013, then maintained itself in 2014-2017, then declined in 2018-2020 but with a resurgence this year.
Quoting both of these, since it is relevant to both -
2010 was the end of an era in a sense - it was the last year when winners were largely determined by lopsided trades. Through 2010, there was a tradition where the best teams tended to extract a lot of value from "trading down" to a GM desperate for a particular player. IIRC, the top 4 teams in 2010 were way better than anyone else, and all of them were big into the "trading down" game. My championship winner traded a late 2nd round pick and garbage for what would eventually become 2 3rd round picks - one early (Borje Salming) and one late (Sid Abel), without even sacrificing my 4th round pick (Busher Jackson). My 1st round pick (4th overall) had been Gordie Howe BTW).
GMs who weren't around prior to 2011 have no idea just how out of control trading had become. To even be competitive, you pretty much had to hoard good picks by trading down to a GM desperate for a particular player. I don't even remember who the GM who really wanted my late 2nd got - I think it was a dman only slightly better than Salming.
I believe the "trade committee" bureaucracy was created for ATD 2011.
On the other hand, ATD2011 feels like the end of an era, because that was the absolute peak of the ATD in terms of sheer # of GMs.
___________
IMO, Rob Scuderi's 2016 Champion is probably the single best ATD winner ever, relative the the competition.
His 2015 team though - I think I'm just now finally over the sting of losing to that team on the BS 2nd tiebreak of "3 stars" - freaking Jean Beliveau. Edit: Nevermind, I got two years mixed up in my mind, Rob's Beliveau team didn't win it all.