I agree with you 100% here except, a family has to pay tuition at Leo and Hales. But yes, there's a long history of kids transferring out of CCL schools for a variety of reasons but good amount of it is a result some form of the following, academic issues, off the field stuff, transportation or cost concerns.
A few reasons why I believe Phillips is set up well to be a public powerhouse for the foreseeable future is as follows:
1. Public- NO TUITION (not sure of any boundary restrictions within 606-- zip code)
2. Recent history of winning/only CPS state title- personally I think they should petition up going forward but why should they care what I think
3. Recent history/number of scholarship players at the collegiate level
4. Academic support- at no cost, students are getting whatever support they need to qualify academically for NCAA athletics. I'm not here to comment on the school's curriculum and level of difficulty. From the outside, Phillips appears to check all the boxes in terms of making sure their kids qualify to receive athletic scholarships.
Based off just these reasons, I don't see why any family of an 8th grader on the South Side who thinks their kid has a shot at playing college football, wouldn't strongly consider Phillips as a high school option.