Where They Went Wrong

The Jedi's problem was, they generalized too much.  They went from "Using the Force while experiencing negative emotions can lead to becoming a bad person" to "Don't use the Force unless you're calm" to "We're not going to teach you to use the Force at all unless you're calm all the time".  That's why they had to get kids so early, to make sure they were still malleable enough to have the proper attitude instilled.  When a nine-year-old is "too old"--which he was--there's a problem.  And the problem with Anikin was, they got him when he was too old to be taught their particular variety of denial of emotion, but they, who'd been repressing themselves for generations, didn't know how to teach him to handle the emotions he was having.  It's possible Qui Gon could have managed it, but Obi Wan wasn't unorthodox enough.  (He learned, though, in time to not totally fuck up Luke.)  It didn't help that they were used to dealing with kids who'd never dream of going against the Jedi strictures, so no one managed to pick up on the signs of his crush on Padmé in time to do anything useful about it.

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