For me this is easy. Since 1999 I've drafted in a 30-team NHL sim league a week
before the real-life NHL draft, so I have a documented history. When you're drafting before the NHL draft, sometimes your late-round picks don't even get drafted in real life.
My early drafting years were really bad until I started my learning hard lessons in what to look for in prospects, and scouting better starting around 2004.
Disclaimer: I know that nobody cares about other people's fantasy teams, but the topic somewhat calls for it
Here are my picks, in other words players I at some point believed in:
1999:
49th: Niklas Hagman
132th: Karel Mosovsky
133th: Adam Johnson
150th: Andrew Ianiero
153rd: Kenric Exner
206th: Antti Jokela
2000:
19th: Alexei Mikhnov
49th: Alexander Tatarinov
79th: Jakob Cutta
109th: Andrew Downing
229th: Derrick Byfuglien
259th: Eric Clark
2001:
22nd: Lukas Krajicek
59th: Adam Munro
90th: Jussi Timonen
122nd: Maxim Suchinsky
220th: Dusan Salficky
284th: Vaclav Kos
2002:
25th: Chris Higgins
55th: Cam Ward
56th: Brian McConnell
86th: Konstantin Korneev
127th: Matt Greene
152nd: Jarkko Immonen
185th: John Adams
2003:
56th: Joshua Hennessy
120th: Kevin Nastiuk
152nd: Jeremy Williams
182nd: Anton Khovrin
214th: Jan Hejda
2004:
26th: Johan Fransson
56th: Mark Fistric
117th: Alexander Nikulin
151st: Clayton Stoner
181st: Troy Brouwer
216th: Karri Ramo
248th: Petteri Wirtanen
2005:
7th: Jack Skille
54th: Tomas Pospisil
67th: Niklas Hjalmarsson
115th: Sergei Kostitsyn
180th: Dev Heshmatpour
228th: Drew Fisher
2006:
7th: Derrick Brassard
37th: Alexander Vasyunov (RIP)
81st: Brad Marchand
89th: Harrison Reed
110th: Jonas Junland
120th: Carter Camper
2007:
2nd: Patrick Kane
19th Oscar Moller
31st Bill Sweatt
61st Olivier Fortier
181st Jamie Benn
182nd Matt Frattin
2008:
4th: Alex Pietrangelo
34th: Jared Staal
64th: Justin Jokinen
124th: Sergei Ostapchuk
184th: Teemu Hartikainen
2009:
11th: Ryan Ellis
161st: Kristian Nakyva
191st: Henrik Thegel
2010:
33rd: Jordan Weal
55th: Jared Knight
125th: Sam Carrick
146th: Joe Rogalski
155th: Zach Hyman
188th: Alex Guptill
2011:
5th: Sean Couturier
10th: Mark Scheifele
11th: Ryan Murphy
77th: Mattias Backman
104th: Matt McNeely
190th: Lars Volden
2012:
30th: Ludwig Bystrom
60th: Calle Andersson
115th: Jaccob Slavin
180th: Tobias Tornqvist
2013:
24th: Ryan Hartman
105th: Colton Parayko
143rd: Andrew Copp
144th: Sean Maguire
200th: Tucker Poolman
204th: Jayden Hart
2014:
25th: Travis Sanheim
55th: Brycen Martin
86th: Mattias Janmark
146th: Rourke Chartier
176th: Michael Prapavessis
178th: Kyle Wood
201st: Liam Pecararo
2015:
24th: Noah Juulsen
54th: Nikita Korostelev
57th: Mitchell Vande Sompel
84th: Jesper Lindgren
114th: Connor Hobbs
133rd: Kevin Stenlund
144th: Matt Bradley
175th: Joey Daccord
205th: Christoffer Ehn