The Star Trek: Deep Space Nine episode in which Captain Benjamin Sisko (Avery Brooks) met Captain James T. Kirk (William Shatner) was so much better than when Captain Jean-Luc Picard (Patrick Stewart) met Kirk in the Star Trek movie Generations. In the 1990s, Kirk, the Captain of the Starship Enterprise in Star Trek: The Original Series, encountered the Captains of the first two spinoff series. But while Kirk's feature film team up with Picard was given pomp and circumstance — especially since it ended with Kirk being killed off from the franchise — Sisko's brief man-to-man with the Enterprise's commander on DS9 was much more fun and satisfying for Trekkers.
By the early 1990s, Star Trek: The Next Generation had proven to be a massive hit in syndication and Paramount decided it was time to transition the series to movies to replace The Original Series cast. Paramount wanted the inaugural TNG movie to be a historic team-up of Picard and Kirk's crews, but when most of the TOS actors declined to participate, the focus shifted to Kirk and Picard joining forces as the selling point of 1994's Star Trek Generations. In William Shatner's final appearance as the Star Trek icon, Kirk helped Picard stop Dr. Tolian Soran (Malcolm McDowell) from destroying a star. This involved Picard and Kirk brawling with Soran on top of a mountain in Star Trek Generations' climactic confrontation, and Kirk died in the process of foiling the villain. Considering Kirk's lofty status in Star Trek, it was an underwhelming demise for the captain that started it all.
It fell to Star Trek: Deep Space Nine to celebrate the franchise's 30th anniversary in 1996 and they did it in style with the brilliant episode "Trials and Tribble-ations." In this time travel romp, Captain Sisko and the crew of the U.S.S. Defiant journeyed back to the 23rd century to stop the assassination of Captain Kirk on space station K-7. DS9 went all-out by recreating the classic TOS episode "The Trouble With Tribbles"; the actors wore The Original Series' colorful uniforms and, in a few scenes, DS9's actors were digitally inserted into memorable moments from the original episode. The results were amazingly convincing and hilarious, like Kirk dressing down the Enterprise crew for brawling with the Klingons, which included his yelling at DS9's Chief Miles O'Brien (Colm Meaney) and Dr. Julian Bashir (Alexander Siddig). This also retconned TOS so that canonically, Sisko and crew were in the episode all along. But DS9 saved the best part for last: Sisko meeting Kirk.
Even though they had saved Kirk's life from an exploding Tribble (and the Captain was none the wiser), Sisko couldn't return to his own time because "there was one more thing [he] had to do..." and that was meet face-to-face with the Starfleet icon. Sisko resisted the urge to pepper Kirk with questions and, instead, he kept their encounter brief by posing as a Lieutenant on temporary assignment aboard the Enterprise and settling for simply telling Kirk that it was an honor serving with him. Kirk politely nodded while Sisko left happily, although Spock obviously found the moment to be curious. But the meeting ended "Trials and Tribble-ations" on a perfect grace note and the quick chat between Kirk and Sisko was electric.
Although DS9 repurposed old footage of Kirk and William Shatner did not appear in the flesh, the time-travel shenanigans meant Sisko got to meet Kirk in his prime and DS9 got to honor TOS while simultaneously delivering an all-time classic episode. Ironically, Sisko met also Picard in DS9's premiere episode, "Emissary," and he had a hostile rapport with the Captain of the Enterprise-D. So, it was especially sweet and rewarding for Star Trek fans to see Deep Space Nine's commander so respectful towards Kirk, the original Captain of the Enterprise.
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