It was hardly “extortion”. It was 5-10% of each state’s federal highway funding. Indeed, the reason SCOTUS said it was okay was because the amount at issue wasn’t “coercive”.
Puerto Rico is not entitled to receive funding “apportioned to states” because it’s not a state. The Federal Aid Highway Act expressly provided that highway funds could only be “apportioned to states”. Territorial highway funding comes from a different program. The justification for pressuring states to adopt the 21+ drinking age doesn’t apply to Puerto Rico, because you can’t drive anywhere from there.*
*The rationale for the National Minimum Drinking Age Act was that kids would drive to states with lower drinking ages, get loaded, and then drive home drunk. Invariably, they killed lots of border-area residents in the process. The same rationale applies to Hawaii, but it does get interstate highway funds even though it has no “interstate” highways.
So was the exemption for “medicinal purposes” (much like “medical marijuana” is today in CA).
IIRC you could be stuff like hopes and grape produce with explicit step by step instructions warning you what not to do lest you end up with a forbidden intoxicating liquor.
Fun fact all 3 of Hawaii’s interstate highways on Oahu. IIRC they all connect military bases.
Not entirely. They run by or near many of them but it’s a small island with limited areas for roads and military bases. The H1 doesn’t connect at either end to a base. The H3 probably had the connection to MCBH as one of its justifications.