Star Trek: Deep Space Nine. The most consistently good Trek show (fight me!)
I'm trying... I'm about three season in. Not warming up to it yet. I'm watching it no matter what. Bit by bit.
To appreciate it, you need to remember that it first aired in 1993. Special effects were still largely done on-set and there was still pretty tight network and FCC control over content (e.g. each episode still needed to be 'self contained'). Still, DS9 was different in having a continuous story, mutli-epsiode arcs and was 'grittier' than the previous ST or TNG while still existing within Roddenberry's world of advanced scientific human Utopia. It melded a lot more aliens together, with Humans, Ferengi, Klingons, Cardassians and the Dominion all present in almost every episode.
I think DS9 had/has the DNA to be an amazing series on one of the streaming networks (e.g. Netflix) where they don't have to pay much attention to broadcasting guidelines or commericial breaks or self-contained episodes. Alas, I don't see that happening. They'll draft up some completely different Star Trek series which will feel more like Abrams or Lin than Avery Brooks (DS9) or Roddenberry.
DS9 wasn't a bad show . . . but it wasn't Star Trek. It abandoned all of the fundamental concepts and ideas that Roddenberry wanted to do with the series. It was intended to be grittier and darker, dealing with social conflict, war, scarcity, terrorism (all issues that were largely supposed to have been solved in Roddenberry's universe). While it seemed pretty good at the time, it seems to have aged worse than TNG or the original series.
I disagree. I think it fit nicely into the Star Trek cannon - but showed how the United Federation of Planets merged with the other empires that didn't necessarily fit into their world view of scientific utopia and advancement of knowledge for everyone's benefit. You had the main character who was in many ways superior but struggled to understand and become more 'human' (Oto), you had the external threat (Dominion), the diversified group cohesively working together under a command structure (all the officers), and then a lot of squabbling between non-members which Sisco tried to mediate while maintaining the Prime Directive.
Oops... have we strayed from Trump now? Hmm... I don't think Trump would make a very good Star Fleet officer. For one, his 'bone spurs' would be healed by a tricorder in seconds.