About two years post-seizure, the bureau returned Martin's money—shortly after she filed a nationwide class-action lawsuit. But while the bureau may have hoped that would persuade her to drop it, she has continued with her suit, which was back in court last week and seeks a ruling that will prevent the FBI from proceeding with others as it did with her.
I've listened to a series of podcasts (More Perfect) where it became clear to me that in the US to get lawsuits go all the way to the Supreme Court, you need both a case (de jure) and a plaintiff that is marketable. This is not a diss on Linda Martin. Going forward with this case in a attempt to get civil forfeiture more constrained after getting your money back is heroic. Just saying that the US legal system needs heroes and that there is a selection mechanism in place for heroes.
Plessy's "violation" of the despicable Separate Car Act was staged, with the conductor and private detective part fully aware of the planning. https://en.wikipedia.org/wiki/Homer_Plessy points out that the early test case planning included looking for a woman of "not more than one-eight colored blood" as the possible plaintiff.
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) 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.)
