USMA class of 1991.
There are really 3 ways into an Academy. First, the politically connected, but they still need to meet minimum academy standards. Second, athletes. Academy helps find them an appointment. Third, prior service. People who come out of the service, who have an excelkent record and got the attention of the right brass, who help find them a way. Fourth (my way in) involves young people who do well in school, who onmay earn a varsity letter even if not a collegiate level athlete, who earned an Eagle Scout medal or shown leadership in other ways. Apply. Get a nomination, an appointment, and an admission.
Now, it is not completely free. There is an inital cost to cover initial uniforms and clothing, some equipment, I think that a laptop is now a part of that. In 1987, I think it was $1,800 for me. And there are scholarships to cover this for those in need. After that, you trade future service for the cost of uniforms, gear, etc. And, you actually earn a salary as a cadet.
So, there you go. Yes, there are scholarships. Yes, its completely possible for a senior brass to offer help getting in.