2012 #6 Damian Lillard
Should've taken: Damian Lillard! Good job Olshey (or WAS it?)
2012 #10 Meyers Leonard
Should've taken: Draymond Green (oops - but then, a lot of people screwed that one up)
2012 #40 Will Barton
Should've taken: Will Barton. But actually should've traded 40 and 41 (Tyshawn Taylor - we traded him) to move up for Khris Middleton.
2013 #10 CJ McCollum
Should've taken: Giannis MVP Antetokounmpo
Yes, sure, a lot of people passed, but the Bucks didn't, and you can always trade down in those circumstances, like the Mavs did when they got Nowitzki
2013 #31 Allen Crabbe
Should've taken: NOBODY. There's nobody good after Crabbe, but we actually had to buy that pick and it wasn't worth it in the end.
2015 #23 Rondae Hollis-Jefferson
I was happy when we drafted him but sad again when we traded him for Plumlee. But as Plumlee got us THE MIGHTY NURK I'm not gonna complain. However:
Should've taken: Josh Richardson (40), Montrezl Harrel (32), Kevon Looney (30)
2015 #41 Pat Connaughton
Should've taken: Norman Powell, or bought a pick a bit higher and taken Richardson.
2015 #54 Dani Diez
Should've taken: NOBODY. Why buy a pick for this schmo? He has stumpy arms and doesn't even look good in Spain. Or, if you like take Quinn Cook or TJ McConnell (both undrafted)
2016 #47 Jake Layman
Should've taken: Georges Niang (50) or FRED VANVLEET (undrafted)
2017 #10 Zach Collins (boy, we're the #10 team, aren't we?)
Should've taken: Donovan Mitchell, Jarrett Allen
2017 #26 Caleb Swanigan
Should've taken: Kuzma, Josh Hart (hey, we could've traded for Anthony Davis!)
Not gonna grade Simons and Trent onward yet.
Overall: not terrible - mostly useful, surprisingly so for second rounders, but could have Giannis, Draymond, Donovan Mitchell, Josh Richardson and Fred VanVleet