Smash Williams
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2010Actually I used that one because of the Kentucky love fest that goes on in the draft where guys that should not be drafted in the first round end up doing so.
John Wall
DeMarcus Cousins
Patrick Patterson
Eric Bledsoe
Daniel Orton
2011
Brandon Knight
Enes Kanter
2012
Anthony Davis
Michael Kidd-Gilchrist
Terrence Jones
Marquis Teague
2013
Nerlens Noel
Archie Goodwin
2014
Julius Randle
James Young
Out of the 15 Kentucky players drafted in the first round during Calipari's tenure...
-10 have proven themselves to be one of the top 30 players in their respective draft classes, without question
-2 washed out after being picked 29th (Orton, Teague)
-1 is a second-year player (also drafted 29th) struggling to get minutes on a team that had a loaded backcourt (Goodwin)
-2 are currently rookies, one of whom broke his leg in the season opener (Randle, Young)
Unless you want to declare James Young a complete bust after one season, at most three of UK's 15 first rounders should not have gone in the first round--in hindsight. All three of those guys were drafted 29th, so they barely even made it in the first round anyway. (The typical draft doesn't even produce 29 legitimate NBA players, but that's another matter)
As for Orton in particular, he was a late first round pick for the same reason that BJ Mullens and Fab Melo were: the bust ratio is so high at that point in the draft that teams love to take potentially high-reward gambles on unpolished big men who displayed enough raw talent to be 5-star recruits in high school. It had nothing to do with Kentucky.
Also, who were the players that were so clearly better than Orton at #29? There is Lance Stephenson, who dropped all the way to #40, and Hassan Whiteside, who bounced around the D-League, China, and Lebanon the last few years after being picked at #33.