WCE didn’t win a flag because of this trade. They won one for a whole heap of reasons. Just Carlton didn’t get to flag because of this trade, it was for a whole heap of reasons.
Thats it in a nutshell. You can trot out the 'premierships are the only thing that matter's line and declare WC 'won' the trade if it makes you feel warm and fuzzy, the obvious fact is there are a heap of factors just as pertinent as Kennedy in WC's current situation and a heap that are definitely more pertinent than Judd in Carlton's.
Kinda moot point anyway (evaluating the trade as if there was a 'choice' not to do it). Every club in the league does that trade in a heartbeat if they can, and those with the picks were going just as hard as Carlton - we just happened to have the extra pick.