This is really well put and get's to the heart of Obama's politics. Having a kinder gentler capitalism is something Obama can agree with. Attempting to lift all boats so long as it is top down with meritocracy's winner boats first, is okay with the former president.
Admitting any kind of real problem with meritocracy though is off the table. So that means you can't nationalize industries, you can't give directly to the poor except in an emergency, and you especially can't question the basic idea that the educated should be more powerful and rich than the less educated.
Since education is the key to Obama's ideas of meritocracy he of course recommends books.
Obama definitely does not understand the book Caste where Wilkerson says in an NYT article:
For this reason, many people — including those we might see as good and kind people — could be casteist, meaning invested in keeping the hierarchy as it is or content to do nothing to change it, but not racist in the classical sense, not active and openly hateful of this or that group.
So I think the vast majority of Obama's reading list does not challenge his ideas of meritocracy and where occasionally some book does he just is not aware of it.