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

A deadly plague struck the crew of the Enterprise before stardate 5843.7. Seeking a cure on Holberg 917G, Kirk encountered Flint, a near-immortal Human. Born as Akharin, during Earth's 4th millennium BC in Mesopotamia, Flint had later been known as Solomon, Alexander the Great, and Leonardo da Vinci, among other famous identities. Kirk fell in love with Rayna Kapec, an android Flint had built to give him company in his final days of seclusion. () A century later, Captain Janeway of the expressed some doubt about this encounter. ()
An incredibly realistic simulacrum of Kirk's hero, the American President , greeted the Enterprise on stardate 5906.4. Following an invitation to the surface of the planet Excalbia, the silicon-based Excalbians re-created the historical figures , , , , and . Kirk, Spock, Lincoln, and Surak were pitted against the others as means for the Excalbians to understand the nature and strength of good versus evil. During the battle, Kirk received perhaps on of his most meaningful compliments from the form of Lincoln, who was struck by Kirk's propensity to take the offensive when required, when his he asked of Kirk, "Do you drink whiskey?" After Kirk responded, "Occasionally; why?" Lincoln answered, "Because you have qualities very much like those of another man I admire greatly, General Grant." ()
After responding to a distress call from his former lover, Janice Lester, on Camus II, Kirk arrived at her bedside, where she appeared to be near death. Not expecting danger, Kirk was easily ensnared. Lester activated the life-entity transfer device and was immediately thrilled by her possession of Kirk's body. The transfer would eventually return the exchanged persona to its original body, as long as both remained alive. Drugged and disoriented within Lester's body, Kirk was easy prey, but Lester's spontaneous gloating monologue prevented her from strangling Kirk before Dr. Leonard McCoy arrived. 
Kirk was still a liability as long as he remained alive in sickbay, but the exclusive care of Dr. Coleman kept Kirk isolated from the crew, however, Spock discovered the truth of the situation through a brief mind meld with the imprisoned Kirk in Lester's body, but their attempted escape was halted by security officers ignorant of the captain's strange new behavior.
During Lester's final attempt to kill Kirk, the two touched in a brief struggle, and the misplaced personalities returned to their proper bodies. Broken, incoherent, and sobbing in her complete failure, Kirk couldn't help but feel sorry for the poor, mentally unstable, twisted-minded woman, who was driven mad not only by her ambition of craving the power to command a starship, but also her hatred and jealousy of the captain she once loved, then wanted dead. Kirk felt her life could have been as rich as any woman's, "if only…" ()
In 2269, Kirk encountered Cyrano Jones and Koloth once again, saving Jones when his vessel, a Federation scout ship, was destroyed by the . Koloth demanded that Kirk hand Jones over and Kirk defiantly told him that the first Klingon to board the Enterprise would be the last Klingon. ()
Kirk, along with Spock, Sulu, and McCoy visited the planet Phylos, where he encountered a clone of Stavos Keniclius, a scientist from the Eugenics Wars. Spock was abducted by Swoopers and cloned, which became known as Spock Two. Kirk later lead a rescue mission to get Spock back, which was successful. Before leaving Phylos, Kirk told Stavos Keniclius 5 that Spock Two could stay with him and together they could attempt to bring the Phylosian civilization back from the dead. ()
Late the same year, the Enterprise returned to the time planet to once again visit the Guardian of Forever, when he, Spock, and historian Erickson observe the dawn of the civilization. ()
Kirk and his crew were instrumental in stopping a massive matter-energy cloud from consuming the planet Mantilles. Kirk wrestled with the ethical implications of destroying the cloud once it was determined to be a living creature but fortunately, Spock was able to mind meld with it and convinced it to cease its movement toward Mantilles. ()
Kirk lead a landing party that beamed down to inspect Planet Two of the Taurean system. There, he became affected by the glandular secretion of the female members of Theela's species who inhabited there, who were known for controlling the male mind. This drained Kirk of his "life force," causing him to age at a rate of ten years per day. After an all-female security detachment led by Lieutenant Uhura recovered him and the landing party. By using their molecular pattern stored in the transporter system, Kirk and the others were returned to their previous ages. ()
Kirk, together with Spock, were tasked by the Vedala to recover the Soul of the Skorr, which had been stolen and had triggered a racial fury among the Skorr. As a result, they had prepared for war against the known galaxy. Kirk was specifically chosen for the mission for his leadership and adaptability skills. Together with a team consisting of Spock, Lara, Em/3/Green, Sord, and Tchar, they were transported to a world simply named "mad planet" to recover the Soul of the Skorr. Kirk later determined that the thief was Tchar, and together with Spock, he was able to defeat him and get the Soul of the Skorr back using null-gravity combat exercises. ()
Kirk and the Enterprise crew later discovered the long-lost Earth colony Terratin after they had sent out a distress signal. However, the only way the colony believed they could get Kirk's attention was to shrink the crew of the Enterprise down to their size. Upon requesting that the colony's inhabitants be saved, Kirk, after being restored to full-size when he transported down to Terra 10's surface, had the miniature colony beamed aboard the Enterprise and later had it relocated to the planet Verdanis. ()
Kirk, together with Spock and McCoy, beamed down to Lactra VII to locate Lieutenant Commander Tom Markel and other missing officers from the starship after they had been missing for approximately six weeks. While there, Kirk located the missing Ariel officers and encountered the Lactrans. While being held in their "zoo", Kirk faked being ill in order to regain his confiscated communicator and escape with his crewmembers. Unfortunately, it was taken away by a young Lactran and it was beamed up to the Enterprise instead. Upon witnessing this, the Lactrans tried to destroy Kirk's mind after their "child" had disappeared. After it returned to the surface with Montgomery Scott, it told its fellow Lactrans all it had learned about the Federation and the races it encompassed while on the Enterprise, which led them to free Kirk, Spock, McCoy and the Ariel crew. The Lactrans later requested that Starfleet visit their planet again in about twenty or thirty centuries in their time. When Spock told Kirk that it would take some time to figure out long that would actually be, Kirk responded that, regardless, it would not be their problem. ()
In 2270, Kirk and the crew of the Enterprise fell victim to several practical jokes after the ship passed through an energy field near the Romulan Neutral Zone. Passing through the field caused the Enterprises main computer to malfunction and it began erratically playing jokes on the crew. Among the jokes that Kirk had played on him were the computer printing that he was a jerk on the back of his uniform, making him and Spock slip on ice in a corridor, and causing the artificial gravity on the bridge to cut out, making Kirk float to the top of the bridge. ()
Later that year, Kirk welcomed aboard Commodore and Federation Ambassador-at-large, as well as former commanding officer of the Enterprise, Robert April, along with his wife Sarah, on its journey back to Babel, where April was due to be honored before his mandatory retirement. While on the way there, the Enterprise encountered Karla Five and her vessel while it was apparently headed for its destruction at the heart of Beta Niobe supernova. While attempting to save her and her ship, Kirk and his crew were drawn into a reverse universe, where Karla Five was actually from and was intending to return to through the supernova remnant. Kirk, along with his entire crew, began to turn into children while in this universe. Thankfully, due to the efforts of a younger Commodore April taking command of the Enterprise from its captain, Kirk, along with his crew, were all restored to their normal ages when they returned to their own universe. ()
Further exploits of this time included saving the Pelosians from extinction, despite it being a violation of the Prime Directive, such as he had with the Baezians and Chenari years earlier. ()
Reaching the end of its five-year deployment in 2270, Kirk ordered the Enterprise set on a course returning the ship to Earth. ()