Captain James Tiberius Kirk may live in a future where the world has achieved total peace, but that doesn't mean his life is easy. Star Trek's greatest ladies man, besides Commander Riker of course, seems to get out of trouble by using his natural charisma, but sometimes that doesn't work out for Kirk.
While Chris Pine's incarnation has had a few trials here and there, it's William Shatner's version who has had it much harder. It especially seems that as Kirk has gotten older, the universe has had it out for him, with his past actions coming back to bite him.
Dying To Stop Dr. Soran
What better way to start recalling the trials of Kirk's life than recalling how it ended? After being presumed KIA when The Enterprise-B ed through The Nexus at the beginning of Star Trek: Generations, Picard would later find Kirk living his perfect life in The Nexus, but he did convince Kirk to assist in stopping Dr. Soran from destroying an entire system of planets.
During the final battle on Veridian III, Picard managed to stop Soran's probe and kill the mad doctor, but Kirk was fatally injured. After sharing a touching moment with Picard, Kirk ed away, with his last words indicating a sense of realization that this truly was the end of his story.
Being Resurrected By William Shanter's Ego
With Kirk being more or less in the actor's rearview mirror, William Shatner has split his time between acting and writing, with his TekWar novels being his most notable writing accomplishment. Sadly when he was given the chance to write Star Trek novels, his ego ended up being the true author.
The "Shatnerverse" novels see Kirk resurrected by a Romulan-Borg alliance, only to be constantly called in to save the galaxy. Though the idea of Kirk being brought into the 24th Century isn't a bad one, the novels read more like fanfiction than real literature.
Being Exiled To Rura Penthe
In Star Trek VI: The Undiscovered Country, Kirk was begrudgingly assigned to escort Klingon Chancellor Gorkon to Earth in order to conduct peace talks. This turned sour when the Klingon ship was seemingly fired upon by The Enterprise and Gorkon was assassinated by men in Starfleet spacesuits.
Despite proclaiming their innocence, Kirk and Dr. McCoy were tried by The Klingons, found guilty of the crime, and exiled onto the freezing planet Rura Penthe. Forced to work in the mines, Kirk and McCoy were later assisted in their escape by the duplicitous shapeshifter Martia before being rescued by The Enterprise.
Being Demoted
Though it is a far more lighthearted affair than the previous two films, Star Trek IV: The Voyage Home ended with a massive blow being dealt to Kirk's Starfleet status. After saving Earth by bringing back two humpback whales from 1986, Kirk was put on trial by Starfleet for stealing The Enterprise and destroying it.
Kirk is demoted from iral back to Captain and is given a permanent halt in rank. Though the fact that he and his crew had just saved the entire planet ended up sparing him from a far more severe sentence, Kirk was punished for his actions.
City On The Edge Of Forever
"City On The Edge Of Forever" is easily one of the best Star Trek episodes of all time, with a gut-punch of an ending that will have anyone reaching for the tissues. After traveling back to Depression-era NYC in order to save a delusional McCoy, Kirk fell in love with pacifist Edith Keeler.
Unfortunately, Keeler had to die in order to prevent The Nazis from taking over the planet, as her pacifist ideals would have stalled America's entry into World War II. In the end, Kirk ended up making the ultimate sacrifice by stopping McCoy from saving Keeler, which caused her to be run over by a truck.
Losing The Enterprise
After losing Spock in The Wrath of Khan, Kirk returned with his crew to The Genesis Planet in order to save him in The Search For Spock. When that mission was jeopardized by hostile Klingons, Kirk made a major sacrifice in order to stop them from learning Genesis' secrets.
Kirk, with McCoy, Uhura, Scotty, Sulu, and Chekov abandoned the ship just before it was raided by The Klingons, but not before activating the self-destruct protocols, which resulted in the destruction of The Enterprise. The image of the destroyed husk of The Enterprise floating in space is awe-inspiring and haunting, but it isn't the only loss Kirk would suffer in the third film.
Being Forced To Kill Gary Mitchell
A difficult trial Kirk had to overcome occurred during his first appearance in Star Trek's second pilot "Where No Man Has Gone Before." In the episode, Gary Mitchell, an old friend of Kirk's, was granted godlike abilities which turned him into an overwhelming threat.
After failing to maroon him to Delta Vega, Kirk attempted to battle his old friend, but Mitchell had simply become too powerful for Kirk to fight. In the end, Kirk used a phaser to create a rockslide, which crushed Mitchell beneath it.
Losing A New Generation Of Starfleet
The Wrath of Khan is a much darker film than most Star Trek fans would expect going in, with Kirk and his crew being put through Hell by their greatest nemesis. When Khan gains control of The U.S.S. Reliant, he attacks The Enterprise and costs the ship several of her rookie crew.
A casualty of note is that of Pressman, who just so happened to be Scotty's nephew. In one of the most heartbreaking scenes in the movie (and that is saying something), Scotty reveals that Pressman stayed at his post when all the other trainees ran for their lives.
The Death Of Spock
Perhaps the most iconic, moving scene in Star Trek history is when Kirk has to say goodbye to his best friend in The Wrath of Khan. With Khan dead and The Genesis Device no longer a threat, the nightmare seemed like it was finally over, but there was just one last heartbreak for iral Kirk.
Spock had sacrificed his life so that The Enterprise could escape from the explosion that created Genesis, with Kirk only arriving on the scene when it was too late, witnessing Spock's final moments of life. Spock would obviously be resurrected, but his death would affect Kirk for years to come.
The Death Of His Son
Losing a friend is a sad occasion, but that's nothing compared to losing a child. What makes the death of Kirk's son David so tragic is that it felt like Kirk never truly got to know him, as he had only just found out he existed a few days before he was brutally murdered by Klingons.
Kirk was never fond of The Klingon Empire, especially since they were a thorn in his side back in his younger days, but this one action turned him completely against them. In fact, in Star Trek VI, Kirk begged Spock to simply let The Klingons die when their moon was destroyed, as he could never forgive for what they did to his son.