James T. Kirk/Starfleet career/USS Enterprise/Year Four

On stardate 4523.6, the Enterprise was dispatched to Deep Space Station K-7, Koroth, Federation bureaucrats, and myriads of cuddly but prodigious tribbles tested Kirk's patience. (; ) Unknown to Kirk, Benjamin Sisko and the crew of the observed and facilitated his actions after a Bajoran Orb: the Orb of Time brought them from the 24th century; Sisko even got Kirk's autograph (although Kirk thought he was signing a shipping order) and told Kirk that it had been an honor to serve with him. During the same mission, Lieutenant Commander Jadzia Dax expressed her knowledge that Koloth always regretted not getting the chance to face Kirk in battle. ()
While the Enterprise was transporting ambassadors to the Babel Conference of 2268, an Orion agent, Thelev, disguised as an Andorian, stabbed Kirk, puncturing his left lung. ()
Kirk returned to Neural, the site of his first Starfleet assignment, on stardate 4211.4. Klingons had begun supplying the primitive native villagers with firearms, leading them to war on the neighboring . Kirk decided to supply the Hill People with similar weaponry, escalating the conflict, but putting both sides on equal footing. ()
Upon his second encounter with the dikironium cloud creature in 2267, Kirk re-experienced the feelings of guilt over his actions in a previous disastrous incident, aboard the USS Farragut. Exhibiting a single-minded fixation on the destruction of the creature, McCoy and Spock questioned Kirk's emotional condition. But as it proved, phasers were ineffective against the cloud creature; thus, Kirk learned that he could not have stopped it in their previous encounter, and hence that he had nothing to regret. With the help of his former captain's son, Ensign Garrovick, Kirk lured the creature to the planet Tycho IV, destroying it with an antimatter bomb. ()
Kirk found the contaminated society of Sigma Iotia II, based on 1920s Chicago gang culture, puzzling at first, but he quickly warmed to it. Uniting the world's "gangs" under one "boss", the Iotians became a Federation protectorate. ()
Scouts from the Kelvan Empire in the Andromeda Galaxy hijacked the Enterprise for their return voyage on stardate 4657.5. The Enterprise, modified with Kelvan technology, became the first Federation starship known to cross the galactic barrier, briefly leaving the boundary of the Milky Way Galaxy before Kirk and his senior officers overwhelmed the Kelvans and returned to Federation space. ()
Kirk later had his mind displaced into a receptacle in 2268, briefly allowing the ancient being Sargon to live as a corporeal being. ()
After John Gill failed to report in from a cultural observation mission to Ekos, the Enterprise was assigned to investigate. Kirk found his old professor had developed an idealization of Utopian fascism and had abandoned observation for intervention, creating a Nazi-like world government that overwhelmed Gill's best intentions. Kirk aroused the subverted Gill in time to avert Ekos' impending war with neighboring , and heard Gill recant his philosophies before he died. ()
On stardate 4842.6, the Enterprise discovered the Amerind planet, where an ancient race, the "Preservers", had transplanted elements of Native American cultures that had been endangered in centuries past. When an accident separated Kirk from the landing party and caused him to suffer amnesia, Spock was forced to abandon the search and command the Enterprise in its mission, that of the interception of an asteroid on course to hit the planet. For several months, the inhabitants worshiped Kirk as a god called "Kirok". During that time, Kirk took a wife. Upon the Enterprises return and the restoration of his memories, Kirk was able to activate an ancient planetary defense mechanism the Preservers had left behind, and thereby divert the approaching asteroid. ()
Inexplicably to his crew, Kirk began exhibiting bizarre behavior on stardate 5027.3, and ordered the Enterprise across the Romulan Neutral Zone. Three Romulan starships detained the Enterprise, and Kirk and Spock met the Romulan commander aboard her ship, where Kirk's death was faked. The ruse allowed Kirk, surgically altered to look Romulan, to infiltrate the Romulan vessel and steal its cloaking device. Using the device, the Enterprise cloaked and escaped to Federation space, taking along the captured Romulan commander. The entire operation had been designed to give the Federation plausible deniability in case of the mission's failure, and place the culpability on Kirk in that case. ()
Near Tholian space, on stardate 5693.2, the Enterprise discovered the adrift, its crew dead, trapped in a spatial interphase. Tholian commander Loskene responded to the trespass of "recently annexed" Tholian space. Kirk was lost in the interphase and presumed dead. The Enterprise exchanged fire with the Tholians, and the unstable region incited madness among the crew. A second joined the engagement, producing a web to ensnare the Enterprise. After various crew members witnessed Kirk's spectral image, he was retrieved from interphase, and the Enterprise used the rift to escape Tholian entrapment. () Many years later, in 2381, a framed photograph of Kirk in an environmental suit during this mission was hanging on the wall of an old bar at Starbase 25. ()
The Enterprise visited a Federation asylum on Elba II on stardate 5718.3. Kirk's longtime hero, Fleet Captain Garth of Izar, was committed as a patient. Garth, capable of cellular metamorphosis, assumed Kirk's form in an attempt to escape and commandeer the Enterprise. Spock was able to determine which man was truly his captain, and Garth was returned to rehabilitation. ()
At the end of that year, the governing council of the planet attempted to use the Vegan choriomeningitis organisms in Kirk's blood to control their planet's extreme over-population. ()