Benny already went through his lots of mistakes went evil hurt a lot of people phase. By the time he met Dean he'd come out the other side and was ready to be a better person. With Castiel, he was so new to humanity and choice that it makes sense that his betrayals and wrong doings happened after he met Dean and involved Dean.
I did love that Benny made Cas give Dean an explanation. Benny could see and probably feel how much Dean loved Cas and his need to find him and reconnect and how worried he was about him and there Cas was not even hugging Dean back. Benny must've heard some of Dean's nightly prayers to Cas. He saw him torture so many monsters to find him. Benny wasn't about to let the angel get away with anything that could hurt Dean. Wasn't going to let Cas cause Dean any more pain.
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"It's only symbolism puts magic and meaning into anything."
--- Jack Faust (Promethea)
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