The Question as to why Davey was raped is one of the few questions answered in the film.
I think it is important to make it clear that Davey did not know Malcolm McDowell. Malcolm had observed him. Despised him. Probably because Davey was from the poorer classes mixing with the rich/posh people. Malcolm McDowell's character does not seem to be a gangster. Rather an affluent man with power and influence and clearly someone who had people who followed his orders blindly.
However, he is not part of the dark underworld. They go out of their way to show that he has a double life. One a married man, a member of the establishment, but underneath, he obviously has insecurities(like the rape expert said), fears, and a desparate need to have some control over the world around him. I'm sure, Davey just was a kid he saw at a party, and he became fixated on him, and all his hate manifested. Pretty sick. But, to me, Malcolm McDowell clearly says, "he wanted to show the boy what he really was..", fortuanately, we get to see Clive/Will show Malcolm what he really is...
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