Kirk in death

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. Whilst 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 learnt this was a mistake in the timeline, he travelled 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 and The Fate of the Phoenix).

Kirk was, to a degree, famously killed in 2293 aboard USS Enterprise-B when it was hit by the Nexus (TNG film Star Trek: Generations).

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 for the final time (so far) when Tolian Soran caused a metal bridge to collapse around him (TNG film Star Trek: Generations).

Shatnerverse
Kirk's body was resurrected on stardate 48754.2 in 2371 by a joint Borg/Rihannsu organisation in order to kill Picard (TOS novel The Return).