I think maybe where Lee went wrong was seeking knowledge and experience for other people. Several characters state from the very beginning that they don't really know what's up with Lee because he has this smirk, or he won't explain himself, and he's overall very ambiguous. I've always thought that he does everything for the shock value instead of self fulfillment. This may be partially to blame for Lee's naivete and inability to understand any point of view outside of his own.
When he goes to Russia is a double double double (whatever) agent, or at least he wants to be. And, it's not because he believes in one cause or the other, he just likes being important. Can you really have a fulfilling life if all of your accomplishments are based around impressing the rest of the world? This is my problem with Lee, because I don't think you can. I don't see him as his own person, he's more of a tool. It's also why I see him as childish, because mostly children seek the approval of others in this way (they'll do anything to get a reaction and anything to get affirmation )
I agree that DeLillo frames Lee as having a somewhat adolescent psychology, wanting approval and a sense of significance from older men like Kirilenko and de Mohrenschildt, but remember that he's only twenty-three and twenty-four around the assassination, and he has had a rough childhood. These aren't "excuses" but possible explanations of how he may have come to be the way he is.
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