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James T. Kirk has a dubious position as a Starfleet officer who has faced death, literally experienced it, and come back to life, multiple times. While not something to dwell on, those circumstances might be worth noting...
Kirk was killed for perhaps the first time in 2268 when he was shot by Distrellians during the dispute between planets Prastor and Distrell. Due to those planets' abilities to resurrect the dead, Kirk was quickly returned to life, only to be killed there again. He then found himself in those planets' 'afterlife', Arnhall. (TOS novel: Mudd in Your Eye)
Kirk died later the same year when the Arretian Henoch hypoinjected him with a lethal solution whilst Kirk's body was inhabited by Henoch's enemy, Sargon. Luckily, Sargon had greater power, and was able to resurrect both Kirk and himself. (TOS episode: "Return to Tomorrow")
In late 2269, Kirk was murdered by a spiderweb gun wielded by a future version of scientist Georges Mordreaux. When Spock learned this was a mistake in the timeline, he traveled back in time and successfully prevented the murder. (TOS novel: The Entropy Effect)
Even later in 2269, Kirk ran into a burning house to save lives. The building had been set alight by the entity Omne. When the ceiling collapsed on Kirk, killing him and hiding him from sight of his crew, Omne kidnapped his corpse to duplicate it. (TOS novels: The Price of the Phoenix, The Fate of the Phoenix)
Ironically, James T. Kirk yet again managed to "cheat" death in a mission spanning 2270-2290. In the midst of the conflict between the Wumpar and Draselle, his body was left out of synch with the "regular" timeline, 200 years into the past. After spending a full lifetime isolated, Mr. Spock finally determined his friend's whereabouts in space, directing the Enterprise to those coordinates. History was restored, but remnants of the other Kirk's life still existed. By the Enterprise's arrival, alternate-Kirk was marooned and logged his 34 years with his pet, until dying of natural causes. This experience gave the captain further insight into his life's fragile but influential nature, and may have strengthened his long-held belief of his demise when neither Spock or Leonard McCoy were present. (TOS comic: "The Alone" Part 1 & 2)
In 2371, Jean-Luc Picard found Kirk in the Nexus and convinced him to exit it and save humanity once more. Kirk agreed, but was killed when Tolian Soran caused a metal bridge to collapse around him. (TNG movie, novelization & comic adaptation: Star Trek: Generations)
Strange New WorldsEdit
In TOS short story: "Reflections", from Strange New Worlds I, Kirk is visited by the Organians at the moment of his death and they show him the differences that his decisions have made throughout history.