Your historical examples are absolutely fantastic! A more fictionalized dramatization might be season 4 episode 9 of _The Good Wife_ trying to get a DOMA test

Your historical examples are absolutely fantastic! A more fictionalized dramatization might be season 4 episode 9 of _The Good Wife_ trying to get a DOMA test case (https://en.wikipedia.org/wiki/The_Good_Wife_season_4 https://en.wikipedia.org/wiki/The_Good_Wife_season_4) which focuses on the need to lose at the initial trial because SCOTUS is part of the appellate court system. (And, of course, you probably need to lose at state-level appeals as well.)