The double holdback (start kindergarten late, than repeat a grade at some point later) is common among many wealthy families. Middle class and lower families have financial pressures making sure they send their kids to kindergarten on time, and can't afford the extra year of private school tuition later on. Forget about lax - being older gives them an edge academically and socially, which helps them get into the better schools, etc. Than once they graduate from a top college, this fact justifies the nepotism that gets them a plum job.
The rule at most private school leagues is that you can't be 19 to start the school year (8/31) and still be eligible. Normal kids typically enter their senior year at 17, so most of these kids can only be held back 1 year without violating the league rules.
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