This article is from Dec 21st, 2020, but I thought it was really interesting, especially 4 months later.
NHL Mega-Mock Draft: We picked everything to build a league!
The idea was that 32 people would do a draft to build a franchise, and they each had to select 1 city, 1 owner, 1 GM, 1 coach and 1 player. For players, cap hits were not considered, and it didn't matter if they were drafted yet. For GMs and coaches, they didn't have to be current GMs and coaches, or even in hockey. Someone picked Theo Epstein to be GM, and someone else took Florence Schelling, current GM for SC Bern. There were some real head scratchers, even considering that this took place 4 months ago, and some picks that look really bad in hind-sight.
For Rangers related stuff, here are the picks:
1st overall - New York City - Solid pick as the biggest US market (Toronto was taken 10th overall)
13th overall - Alexis Lafreniere - In hindsight, this pick doesn't look as good, but even in the moment, why would you build around a player who hasn't played yet in the NHL? There are dozens of great young players in the NHL to build around. He could have been taken much later.
98th overall - James Dolan - The consensus was that he is a good NHL owner, awful NBA owner, which is pretty much how he is viewed by many Ranger fans.
103rd overall - Artemi Panarin - Craig Custance voted him the best pick of the round. Great player and great value at that point in the draft, but knowing what we know now, I'd probably go Fox. Younger player, who plays a more important position.
118th overall - David Quinn - Quinn was the 12th coach off the board. Selected before him, in order, were Trotz, Gallant, Brind'Amour, Cassidy, Cooper, Vigneault, Green, DeBoer, Quenneville, Julien and Krueger. Gallant, Julien and Krueger have all been fired. Vigneault could be next, maybe Green. Craig Custance voted Quinn the worst pick of the round: "I love David Quinn. My issue with Josh Yohe picking him here is that he’s leaving his ownership selection for the fifth round. Spoiler alert: It doesn’t work out." Yohe ended up getting Melnyk.
119th overall - Jeff Gorton - There was no commentary on this pick. He was the 22nd GM taken (after Sakic, Yzerman, BriseBois, Francis, Rutherford, McPhee, Armstrong, Lamoriello, MacLellan, Kekalainen, Nill, Dubas, Sweeney, Cheveldayoff, Mike Futa, Holland, Waddell, Theo Epstein, Alex Mandrycky, Wilson and Guerin). I think that's kind of crazy, considering what he has done in his career with both Boston and the Rangers. At the very least, he should be ahead of guys like Futa and Mandrycky. Kekalainen and Guerin haven't accomplished anything of note. Wilson's best years are behind him.
149th overall - Chris Drury - Other GMs selected before him, and after Gorton include Eric Tulsky, Hextall, Florence Schelling, McCrimmon, Zito and Craig Conroy. Three more GMs were selected after Drury (Fletcher, Treliving, Brisson). According to Custance: "Chris Drury, who was very much in the mix for the Panthers job, will have a GM job whenever he’s ready."