Actual Pick: The Rock
With the first pick, Vince McMahon selects Kurt Angle to represent Smackdown.
McMahon would probably have inside info that The Rock was going to take an extended leave of absence to film The Rundown, and would want to make sure he had a blue chipper that you could build a brand around with the first pick. So Vince would bypass The Rock and select Kurt Angle, a former two-time WWF Champion and the greatest technical wrestler on the roster.
The pickup of Angle will immediately pay dividends, as he would win two more WWF Championships, one more World Championship, and main event WrestleMania three out of the next four years as a member of the Smackdown roster, stealing the show with Shawn Michaels the other year.
Just because it's the obvious choice doesn't mean it's the wrong one.