Captain Kirk is a magnificent lying bastard.
No disrespect. Being a bastard is possibly his greatest strength, the reason he and the crew of the starship Enterprise survive so many deadly encounters with hostile armies, planet-destroying artificial intelligences, and childlike gods. Where “Bones” McCoy has medical training and knock-out drugs, and Mr. Spock has super strength and super intelligence (and, like, the universe's most effective shoulder massage), Kirk has to rely on his trickster wiles to bluff warlords, seduce alien women, and convince super-computers to self-destruct.
Again and again, Kirk lies his way out of trouble. Either he’s distracting guards by inventing a complicated card game, or he’s beguiling Orion slave girls into betraying their masters. Sometimes he’s lying to protect the future. Sometimes he’s just creatively interpreting his orders to maneuver the Enterprise where he needs it to go. However he chooses to bamboozle his targets, he usually gets away with it, because William Shatner, and thus James Kirk, is an incredibly charming man.
Whole episodes are based on Kirk being a master deceiver. The titular “Corbomite Maneuver” is just bald-faced lying about having a doomsday weapon and hoping his enemy believes him. “The Enterprise Incident” is a complicated cloak and dagger operation against the Romulans that first requires Kirk to pretend to be a man obsessed and then pretend to be a Romulan centurion, roles Kirk clearly relishes playing.
Like any good liar, Kirk loves playing dress-up. That’s how he gets around the Prime Directive, by dressing as a planetary natives and quickly blending in with the surrounding crowd. One of the best parts of “A Piece of the Action” is watching how much fun Kirk has dressing up as a gangster and bullying the poor aliens who have no idea that he captains a flying metal city capable of raining down destruction from space. And if he’s not playing gangster, than he’s playing Nazi, or Roman, or hobo in the ’30s, or his own evil twin.
The point of the Kobayashi Maru story from Star Trek II: Better Than Into Darkness, is not just that Kirk doesn’t believe in “no win scenarios,” but like any true bastard Kirk genuinely believes the rules do not and should not apply to him. Kirk clearly has little patience for Starfleet regulations, or the petty Starfleet bureaucrats that pop up every tenth episode to insist their pet project be done immediately. And he is outright hostile to every god, godling, godlike intelligence, and computer posing as a god the Enterprise runs into. Kirk would have despised Q, and Q would have loved Kirk, if they had ever met. Kirk’s response to anyone with power over him is to lie, to trick them—sometimes with flattery, sometimes with bravado—into making a mistake, and defeating themselves.
These anti-authoritarian tendencies make Kirk an odd authority figure. Kirk doesn’t follow anybody else’s rules, but he expects over 400 men, women, and others to follow his every command. The Klingon Korax isn’t wrong to call Kirk a “tin-plated overbearing, swaggering dictator with delusions of godhood.” Korax is just wrong to think that this is a bad thing. Kirk is a free thinking man in a fleet that is sometimes too over-burdened by regulations and cold, Vulcan logic. If that means breaking the rules to do the right thing, that Kirk will break some goddamn rules.
Once you see Kirk as a trickster, it makes Harry Mudd one of the more interesting, and I think most underused, Star Trek villains. In “Mudd’s Women,” Kirk immediately sees Mudd is a con-man, but a terrible one. Mudd is too flamboyant, too greedy, too obviously out to make a score. Mudd could never have convinced Star Fleet to entrust him with an entire starship. At the same time, Mudd recognizes that Kirk is a con-man himself, which is made explicit at the end of “I, Mudd” when Mudd and Kirk have to team up to, once again, trick an all powerful artificial intelligence into destroying itself. And even then Kirk has the last laugh by creating a particularly cruel trap for Mudd.
Of course, this is mostly about Shatner’s take on Kirk. For Chris Pine’s Kirk, being a magnificent bastard isn’t a virtue, but rather a childish impulse he needs to outgrow. Stealing cars, getting into bar fights, seducing Orion women, and even cheating the Kobayashi Maru test demonstrate Kirk's immaturity, his unfitness for command. He needs to move past them to gain Spock's and his crew’s respect. And the process is on-going. His reckless, rule-breaking quest for vengeance in Star Trek: Not as Good as Wrath of Khan leads him into a trap that almost sparks an all-out war with the Klingons and destroys a good chunk of San Francisco, leading to that rarest of Kirk moments, the humble apology.
So, on the one hand, I kind of like this change. It keeps the character consistent, but demonstrates the flaws that were always present. Shatner’s Kirk can get away with bullshitting his way across the galaxy because Shatner’s Kirk is never, ever wrong. (Okay, rarely wrong). The moment we accept that Pine’s Kirk is a fallible human being, his righteous rebellion looks more like self-righteous, delusional arrogance (see Korax, above).
On the other hand, if Pine’s Kirk ever stops being a real bastard, then he becomes a fairly boring, generic square jawed space captain. And it’s honestly charming that the original hero of the Star Trek franchise isn’t the smartest, or strongest, or bravest, or most moral man, but the most creative one. The cleverest one. The best liar, and the best actor, and the best storyteller. Captain Kirk is a man who quickly creates new worlds, characters, and scenarios that the people around him instantly believe and are sucked into.
Which is why we love that magnificent bastard.