The offer might be good, but you said it was still on the table and that is not what the article said. Just pointing out your misstatement.
You note that he should have taken the $100K then since he would never make it up later. I disagree. Two years ago he is offered $100K. Now after two years of running he is offered a contract at $200K (article says he would command a contract in that neighborhood), so two years where he missed out on $200K, now he has a contract with double that and voila in two years ($200K x 2 = $400K) he is where he would have been in four years under the prior contract - which for arguments sake would have been four years. Didn't miss a penny. Good chance that because he passed on the contract after high school he will actually make more since he can now possible pick up even more money in incentives.
You made a choice to not put your parents in the position to go into debt. Your choice - got that. His parents and Rupp made a different decision. That's their decision.
Parents go into debt all the time to send their kids to the best school, give them their wants - computers, cell phones, iPods, ect...They do it because they love their children and want the best for them. Rupp's parents are no different. They are raising their son and perhaps the effort is measured in dollars - $45,000 according to the article, but that is because they want him to succeed and achieve his goals.
Frankly I can only imagine you are jealous of his achievements. You attack him for decisions made mutually by his parents and him. I'm sure at some point in your life your parents made a sacrifice or two for you - bought you running shoes when maybe you should have gotten a job so you could afford them. Yes $45,000 is a lot, but it's their choice and they are free to do what they want with it.