Most of the prestigious people I can name aren't prestigious because of their academic achievement, that is for sure - so it isn't obvious why an academic institution should be prestigious full stop. They all teach a similar syllabus, and most professors are remarkably talented. Harvard is prestigious because the students that go to Harvard are well connected, not because Harvard is imparting some superior secret sauce to its students. The selling point is the network of other people who are important, eg, the children of the sort of people who went to Harvard.
We don't give people standing or estimation from academic or athletic ability except in extreme edge cases (much more extreme than college admission). There is a strong correlation between intelligence and prestige, but that is because smart people make decisions that earn them prestige more than because academic ability is prestigious.
Not saying it's a morally correct, but that's 's how (American) society works. We aren't good at predicting a child's success so we fall back on historical (familial) data.
Freckles almost certainly has additional stressors in his life, since he maintains his scholarship(s), works outside of class, frets over his student loans, and has to be careful how he spends what little cash he has.
In contrast, Richie has a pretty carefree existence which he likely spends developing relationships with other rich kids. He can study if he needs to, pay for private tutors, etc.
Plus, from the perspective of University The Business™, Richie is more likely to inherit wealth and business opportunities that make him more likely to donate to the school in the future; he's a better investment than Freckles.
Right. But that's part of the point, is it not? Those factors were almost a non-issue for me in Germany. Having no tuition, I had to work part-time to pay for rent, food, and recreational activities, but that wasn't nearly stressful or time consuming enough to impact my studies (or even my social life).
As such, "student loans" are also not really a thing in Germany. I did take a loan of a few thousand Euros towards the end of my studies, in order to be able to focus on my degree without a job and still have a roof over my head, but I was able to repay all of it very quickly as soon as I entered the workforce.
Meaning, those disadvantages for non-affluent people at ivy league universities are entirely self-created, and very likely have the net effect of promoting students who are innately worse but financially better off to success.
[1] In the sense that they're not academically or athletically at the top of the heap.