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The people in charge of TNG by that point were creatively bankrupt. It would have been a fiasco.

Also, the idea just doesn’t fit Star Trek. It isn’t a comic book franchise, where fan-pleasing callbacks and crossovers are baked into the formula. In Star Trek media, callbacks and crossovers have tended to be some of the worst stories.

This episode was probably peak Dukat. Unfortunately, I don’t think they stuck the landing for his character arc. His descent into insane mustache twirling villainy in the last season was not very interesting. By the finale, the Dukat part was by far the weakest of the simultaneous plot threads.

To avoid paying royalties, I imagine. Hollywood accounting is craaaaazy.

Measure of a Man was groundbreaking but feels pretty dated to watch. Back when it aired, the idea that sentient AIs should be treated as humans was far from the mainstream. Today, we’ve seen so many sympathetic robots in pop culture (including, of course, Data) that the situation is reversed: the arguments aired against Data in this episode seem shockingly bigoted.

Imagine if the plot contrived to make Riker get up in front of the court to argue for slavery – even if he’s clearly labelled as playing devil’s advocate, it feels beyond the pale.

You gotta remember that DS9 is set in the space version of a third world country. This isn’t Federation territory, and the Federation’s presence is on thin ice throughout the series.