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  • Anvilicious: Issue 29's heavy-handedness about the Zuynans' slaughter of the B'Tin while attempting to seize their land.
  • Complete Monster: Pitkemeni, from issues #27 & 28 of Volume 2, is the Minister of Justice for Pilkor III, a small isolationist world on the border between the Federation and the Romulan Empire. Pitkemeni is a major player in a Government Conspiracy to take Pilkor III from a small xenophobic planet to a major player in galactic affairs. Pitkemeni and other government officials kidnap 100 random citizens of Pilkor III, put implants in their brains to give them False Memories and place them on a colony on another world. Pitkemeni's forces disguise themselves as Romulans and attack the colony, killing almost everyone there. Pitkemeni then kidnaps Tred Kegin, the husband of Victoria Leigh, a human living on Pilkor III, who is an old friend of Captain Kirk. Pitkemeni threatens to kill Tred, unless Leigh lures Kirk and the Enterprise to the site of the destroyed colony. Pitkemeni is hoping to frame the Romulans for this crime, so that the Federation will declare war on the Romulans to head off a new Romulan offensive. Pitkemeni hopes this war will destroy every Romulan and Federation colony in the sector, so that Pilkor III can colonize the sector.
  • Harsher in Hindsight: During the Who Killed Captain Kirk? saga, Kirk snaps at William Bearclaw for his blatant racism, especially towards a Klingon. In Star Trek VI: The Undiscovered Country, Kirk's racism towards the Klingons over the death of his son is one of the driving points of the movie.
  • Heartwarming Moments: When Sarek expresses concern about what life will by like after he outlives Amanda, he asks Spock what friendship is like:
    Spock: It is knowing there is one—or more than one—who will accept you as you are. One who seeks out your opinion and is pleased to hear it. One who commands loyalty, not because it is expected, but because you are happy to give it. One who you are pleased to see, even at a time when you would rather see no one. A friend is someone who would call you a "pointy-eared hobgoblin"—and yet you would trust him with your soul. It is difficult to define...except in human terms.
    Sarek: This is most curious.
    Spock: What is, Sarek?
    Sarek: By most of these definitions—I would consider not only Amanda a friend—but you as well.
  • Hilarious in Hindsight:
    • Since Executive Meddling prevented Kirk from having a serious love interest, Sulu was more or less the series' resident Casanova, having flirtations with several women during his stint as a regular. It becomes quite funny when George Takei came out as gay years after the book ended, but especially so when Star Trek Beyond established that Sulu himself is homosexual.note 
      • It gets better: "So Near The Touch," the story told in the first annual, is a story by Takei that centered around Sulu and a former (female) lover.
    • Issue 22 of the second volume reveals that a Nasgul splinter faction set up what is described as an "agricultural colony." The organization is called The Circle, and is led by half-sister of the Salla, and is part of an attempt to wrest control of her people away from her brother. Meanwhile they engage in terrorist activities against a mining colony seeking Federation membership. This wouldn't be the franchise's last terrorist organization by that name.
    • In issue 29, Kirk learns that the population of a planet applying for admission to the Federation has been slaughtering the neighboring species so they can seize their land, and mine the extremely rare and valuable mineral found there. That sounds familiar...
    • Trelane returns in issue 45, intending to "study" Kirk's reputation as The Casanova, pairing him up with a variety of women — such as ex-Yeoman Teresa Ross, and Carol Marcus — to watch Kirk in action. Meanwhile, Enterprise is stalked by an energy reading that Trelane continually moves them out of reach of. Eventually, Trelane reveales what he's really after is Kirk's advice on how to approach women...when it turns out the energy reading Enterprise keeps detecting is a woman of his species. A very possessive woman with the hots for Trelane, and Trelane has no idea how to handle her. Three years after the issue was published, an episode of Star Trek: Voyager finds Q pursuing Janeway, not to learn from her, but to mate with her himself to create a new Q.note  Eventually a jealous Yandere female Q turns up, whom Q was once in a relationship with, and by the end of the episode Q and Q have a child together. Adding extra hilarity to the similarities is the fact that it's popular fanon — and established in Expanded Universe literature — that Trelane's species and the Q are one and the same.
  • Milestone Celebration: The series released special issues to celebrate several moments in the franchise's history, including the 20th and 25th anniversaries. Additionally, issue 50 of the second volume was a double-sized issue.

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