A few options:
1. Wiltfong actually has people connected to each one of the more than 200 top recruits in college football, which changes every year, but all of whom are willing to give a guy who sells recruiting information for a living the real story on what they're going to do with one of the most important decisions of their lives even though they don't know this guy and can't profit from his site.
Or
2. Wiltfong is the man in charge of his site's accuracy numbers, he's not super carefully vetted, and he can pick and choose which predictions he uses for his accuracy rating, and he judiciously switches his "crystal ball" predictions at strategic times to keep that accuracy rate high.
Or
3. He's perfected the art of guessing, much like a poker player, and can pretty accurately read tells from these kids based on interviews, social media posts, etc.
I'm sure there are other options. The option I think is least likely is that he actually knows what these kids are thinking. Some maybe tell him for whatever reason, and great, for those he actually knows. But he cannot know for all of them, nor can he have actual insider information on anything like 91% of them. So there's guesswork, or strategic switching of predictions, or some other way of hedging his bet.
They've clearly perfected the art of guesswork to such a degree of accuracy that they can predict which team is currently "leading" for a player, they can set it up like a race, even though the kid himself may not know where he's going and/or may not have told anyone where he's going, and turn it into a soap-opera like drama with all the wavering over which team a player will pick, first this one and then that one, thus keeping people entertained without having actual factual information most of the time.
I mean, Kim Jong Un is the world's greatest golfer. You should see his scorecard.
Just don't ask to check his numbers.