I think that last sentence is key - but to clarify, I think knowing and celebrating your identity is integral to self-actualisation as is understanding the journey of your ancestors through that shared identity. I think the politicisation of those identities under a faux-Marxist oppressor/oppressed system of viewing the world is inherently flawed.

And working backwards that's what Chappelle was suggesting. LGBTQ+ people encompass very white, very wealthy and very privileged people. It is a group that has been historically oppressed that cannot be denied but there are some within that group who have not experienced political or social oppression in any meaningful way - they may go off and hunt it down on behalf of others (see victim mindset) but that pushes the whole conversation off on a tangent - particularly with other identity based communities. That was Chappelle's wider point I think. The LGBTQ+ community is now (in some aspects) indistinguishable from straight white people.

Oprah Winfrey and the poor white person is a way of understanding the fundamental difference between 'white privilege' and 'economic privilege'. Oprah may have overcome gendered and racial slurs (and I imagine she absolutely did) but such an argument doesn't fly with a predominantly white electorate - what reduces racism is a) racial mixing and b) the reduction of a scarcity mindset. Both of those things are only available under a left-wing Government. You cannot sort out the mess without being in a power, and you cannot get into power when your message is diluted among thousands of niche interest groups.

I would argue (and think it's fair) to say that liberal democracies have become more and more liberal over the last 100 years. We have seen a gentle but inexorable slide toward compassion and inclusion - one that has been halted and partially reversed by the rise of social media and identity politics - particularly when divorced from socialism. MLK was an economic socialist - that bit has largely fallen out of favour. He had so much to say about poverty. That bit hasn't carried through into the echo chambers and is often overlooked by many of the race writers on this platform and elsewhere.

I think your views about people's inability to fold themselves out of a victim mentality are pretty spot on - but your thinking seems binary. We might encourage a dichotomy of 'helpless' or 'hurtful' but such a dichotomy changes from minute to minute and in every situation - however, giving people carte blanche to always identify as 'helpless' causes its own problems. I don't know how old you are, but I'm going to presume you're younger than me and still in your twenties/late twenties. Your generation is the most anxious generation in history - if you bring people up in an environment of 'weaponised offence' and allow people to perpetually cite the reasons why they are more oppressed than any other - you create people who are anxious. Some of the most mentally unhealthy people I have ever spoken with are caught in echo chambers, they cannot function well in pluralistic society. Whenever they meet someone who disagrees with them on anything, they don't engage in the sort of debate we are having - they simply call the other a 'nazi' or any kind of 'ist'.

There is an anti-intellectual movement occurring because the University system (in both our countries) has become problematically influenced by identity politics. See Sokal and then Lindsay, Pluckrose and Boghossian for more on this. We have pushed some aspects of higher education into an ideology factory for a very leftist identarian position and such a thing is very damaging for the fabric of society.

To conclude my point. You're correct, we both want to challenge the existing structures and help people. I think we have to challenge the structures politically and empower people individually. You think we can collectivise the disparate individuals into a cogent political force. I guess we'll have to see which one of us is right. 2024 will give the US the answer - it will either stand behind an identarian Government under Biden/Kamala (ideally the other way round) or you'll have Trump/Graham with a hugely increased majority. It's a gamble. We tried it here with Corbyn and we're now going to be stuck with Boris Johnson for the forseeable.