Pride is not the deadliest sin.

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Pride = ego/arrogance. If you have a massive ego no one wants to know you because you're too full of yourself. Pride in a religious sense is just seen as a narcissistic trait that's a toxic emotion. Instead of saying "I'm proud of you" you should be saying I'm happy for you or you've done really well. To be proud is like saying you're an asset of mine and I'm proud that you've brought me this glory or something like that.

There was an explanation I listened to a while ago and it made a lot of sense.

This one is close enough. It's on the Islam side of stuff but it makes sense if you try to apply non religious stuff to it too. (keep in mind Islam was based off of Christianity so they have very similar beliefs and such).

Biblical pride IMO is more in line with the Greek concept of hubris. The saying “pride goes before a fall” is frequently misinterpreted to say ALL pride leads to failure. It just refers to specific forms of pride that do lead to catastrophe. As to being a deadly sin, yes, absolutely. It is arrogance taken to dangerous extremes. Murder originating in arrogance, attempting outrageous, unnatural acts, putting oneself directly in the face of danger under the arrogant idea that one cannot be harmed because his special status.

Someone who earns a lot of money deserves to enjoy the fruits of his own labor. There is no shame in taking pride in one’s own achievement and reaping the benefits. If you want to buy a new Maserati every week and drive it off a cliff, you’ve earned that right. But if you take a turn too fast showing off your fancy ride, you have to understand that your pride might well cost you your life. Arrogance that pushes a man beyond reason IS deadly, hence why pride really is a deadly sin.

Pride WITHIN reason is the only true humility.