Prior to joining Starfleet McCoy was married. The marriage ended unhappily by 2255; McCoy would complain to Kirk that his wife "took the whole planet" in the divorce, leaving him "nothing but my bones". The phrase was the origin of his nickname, Bones. McCoy had an intense dislike of space, an environment he described as "disease and danger wrapped in darkness and silence." Regardless, his desperate financial situation after the divorce drove him to enlist in Starfleet in 2255 where he was a classmate and friend of James Kirk.1
McCoy was a Cadet at the academy from 2355 to 2358. He was a member of Kirk's crew during the Kobayashi Maru simulation, and was astonished when Kirk repeatedly took the test until finally beating it. When Kirk was placed on academic suspension for his cheating in the test, McCoy injected him with a vaccine so that he could take him aboard the Enterprise as a patient during the Nero crisis.1
When the chief medical officer, Doctor Puri, was killed during Nero's attack on the Enterprise at Vulcan, McCoy inherited the role. He continued to function in this capacity after graduation when James Kirk assumed command of the ship.1
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