My opinion is that perhaps you shouldn’t have mentioned that to him. While it’s true that money can provide more opportunities, I believe it’s more of a systemic issue rather than solely Jack’s fault. Traveling can be a meaningful way to spend money compared to buying unnecessary things. Also, maybe Jack is aware of his luck and understands that others may not be as fortunate. From the way you described the conversation, he didn’t seem to be acting superior to others. I know some wealthy people who actually feel the opposite, thinking they are worse off because they took an easier path in life. I understand your frustration, and it’s valid to address it towards the system rather than directing it solely at one individual who may share similar opinions to yours from a different perspective.

NTA- he’s gotta sort out his own feelings of discomfort about the concept you just presented this poor sheltered man, and that’s his choice to make.

That being said, you might not have wanted to bring this up at a work event since this is the kind of honesty that the social contract usually keeps between more friendly relationships. You may find your experience at the office is different now depending on how office politics trends. You may find some people approve of what you said, bit I’ll bet management won’t like it. Not that they can do anything about it legally, but you might find yourself the target of less than favorable consideration. I don’t you’ll get fired or any kind of overt retaliation, more just that this person and anyone who “takes his side” will at the least be less friendly and helpful.

I’d say you should have stayed quiet, but not for ‘Jack’. Teaching an asshole a life lesson shouldn’t cost you your own peace of mind at work