Considering how big of an impact Captain James T. Kirk (William Shatner) had on Captain of the USS Enterprise, Kirk explored the galaxy as a representative of Starfleet and the United Federation of Planets. This meant that enemies of the Federation also became enemies of Kirk's. Although the Enterprise set out on a mission of peace and exploration, the starship sometimes engaged in battles with enemy ships.
The Enterprise could hold its own in a fight, but then, so could Captain Kirk. Kirk got into quite a few fist-fights throughout Star Trek: The Original Series, several of which famously caused his uniform shirt to rip. On the other hand, some of Kirk's enemies engaged him in a battle of wits, forcing the Enterprise captain to come up with creative solutions to defeat them. From William Shatner to Chris Pine, every version of Captain Kirk has been a quick thinker, who combats his enemies with both his mind and, occasionally, his fists (or phaser).
10 Evil Captain Kirk (William Shatner)
Star Trek: The Original Series Season 1, Episode 5 — "The Enemy Within"
One of James T. Kirk's earliest enemies was none other than himself. In Star Trek's "The Enemy Within," a transporter accident separates Kirk into two halves, one "evil" and one "good." The evil Kirk wreaks havoc on the Enterprise, lashing out and even assaulting Yeoman Janice Rand (Grace Lee Whitney). The good Kirk and the evil Kirk battle it out in engineering, and the good Kirk eventually persuades the evil Kirk that they both need each other to survive.

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With some help from Spock (Leonard Nimoy), Dr. Leonard McCoy (DeForest Kelley), and Chief Engineer Scotty (James Doohan), the two halves of Kirk are restored into one being. Since both Kirks essentially have the same mind, the good Kirk is able to anticipate the choices of his evil counterpart, but the evil Kirk continually fights back. It's a classic Dr. Jekyll and Mr. Hyde story, with Kirk's inner battle brought to life via the transporter.
9 iral Alexander Marcus (Peter Weller) & Khan Noonien Singh (Benedict Cumberbatch)
Star Trek Into Darkness
Star Trek Into Darkness may have received mixed reviews among Star Trek fans, but it did pit Captain Kirk against two formidable villains. iral Marcus betrays everything the Federation stands for by creating a conspiracy to start a war with the Klingon Empire. In J.J. Abrams' Kelvin timeline, Section 31 found Khan's ship, the SS Botany Bay adrift in space, which led iral Marcus to revive the genetically enhanced Khan and force the former tyrant to do his bidding.
Marcus and Khan's actions nearly result in Kirk's death as well, in a controversial scene reminiscent of Spock's death in Star Trek II: The Wrath of Khan.
iral Marcus held Khan's fellow cryogenically frozen Augments as collateral, and Khan was forced to flee after his failed attempt to rescue them. Khan began waging a one-man war against Starfleet, attacking a summit at Starfleet Headquarters and killing iral Christoper Pike (Bruce Greenwood). Since Chris Pine's Kirk never knew his father, he had come to see Pike as a father figure and was understandably devastated by his mentor's death.

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Meanwhile, Khan was Captain Kirk's more direct adversary in Star Trek Into Darkness. Kirk could not physically beat Khan, and he was forced to team with the genetically-engineered man to stop iral Marcus. Kirk ended up sacrificing his life to rescue the USS Enterprise from destruction. It was Spock (Zachary Quinto) who ultimately captured Khan with Lt. Uhura's (Zoe Saldana) help so that Dr. McCoy (Karl Urban) could resurrect Kirk using Khan's "superblood."
8 Tolian Soran (Malcolm McDowell)
Star Trek Generations
After the Borg decimated the El-Aurian population, Tolian Soran became a refugee. As he was being transported to Earth aboard the SS Lakul, the ship got temporarily stuck in the mysterious Nexus realm. As the USS Enterprise-B worked to rescue the El-Aurian refugees, it too became stuck, and Captain Kirk was pulled into the Nexus and presumed lost. From this moment forward, Soran became obsessed with the Nexus and spent the next 78 years concocting a plan to return.

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In 2371, Captain Jean-Luc Picard (Patrick Stewart) and his crew faced off against Soran, determined to prevent his destructive plan. Picard and Soran both ended up in the Nexus, where Picard encountered Kirk. Picard convinced Kirk to leave the Nexus, after which Kirk engaged in a fight with Soran. This confrontation ultimately resulted in Kirk's death, but it gave Picard enough time to thwart Soran's plot. Although Soran's actions led to Kirk's death, he was far from the most interesting villain the Enterprise captain went up against.
7 Gary Mitchell (Gary Lockwood)
Star Trek: The Original Series Season 1, Episode 3 — "Where No Man Has Gone Before"
Lt. Commander Gary Mitchell started out as Kirk's friend, serving aboard the USS Enterprise as the ship's helmsman. When the Enterprise crosses the edge of the known galaxy, Mitchell is knocked unconscious due to the effects of the galactic barrier. When Gary awakens, he possesses telepathy and telekinetic powers. As Mitchell's power continues to grow, he becomes arrogant and eventually hostile.

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Kirk initially refuses to kill his former friend, trying instead to maroon him on a remote planet. Mitchell, however, has grown too powerful to contain, and Kirk is eventually forced to kill him by firing a phaser to create a rockslide. Not only was Mitchell one of the most powerful beings Kirk ever faced, but he was also one of the most tragic. As Kirk points out, Mitchell did not "ask for what happened to him," and Kirk certainly would have rather not had to kill his friend.
6 Kor (John Colicos)
Star Trek: The Original Series Season 1, Episode 26 — "Errand Of Mercy"
"Errand of Mercy" is known for introducing the Klingons, who would, of course, go on to become one of Star Trek's most popular alien species. The Klingons owe much of their later popularity to John Colicos' Kor, who makes quite an impression as Kirk's first true Klingon adversary. Although Kirk initially masquerades as a local villager in "Errand of Mercy," Kor immediately notices that Kirk is different from the other Organians.

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When the Organians reveal Kirk's true identity, Kor its "a certain iration" for Captain Kirk. As Kirk and Kor sit down to talk, it's clear they are nearly evenly matched in intelligence, and in the end, neither truly wins their so-called battle of wills. The Organians reveal themselves to be powerful incorporeal beings, and they put a stop to all hostilities between the Federation and the Klingons. Kirk is glad to avoid a war, but Kor laments that "it would have been glorious."
5 The Romulan Commander (Mark Lenard)
Star Trek: The Original Series Season 1, Episode 14 — "Balance Of Terror"
The Romulans are another alien species who continue to have a presence in modern Star Trek, thanks largely to their captivating introduction in Star Trek's "Balance of Terror." Like John Colicos' Kor, Mark Lenard's Romulan Commander steals the show, presenting an incredibly smart enemy with a strategic mind. When the Enterprise engages a Romulan Bird-of-Prey in battle, the two ships and their commanders are evenly matched.
Kirk and his crew get Starfleet's first look at the Romulans, who bear a striking resemblance to the Vulcans, a relationship later Star Trek shows would explore in more depth.
The result is a tense cat-and-mouse game that the Enterprise almost loses. The Romulan Commander develops a certain respect for Kirk, even acknowledging that "In a different reality, I could have called you friend." In the end, Kirk emerges victorious thanks to his own wits and the efforts of his crew, while one of the Romulan crew ultimately hinders his commander by pressing to attack too soon.

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Star Trek: Strange New Worlds season 1's finale created an alternate future timeline where it was Captain Christopher Pike (Anson Mount) who faced the Romulan Commander (Matthew MacFadzean). However, Captain James T. Kirk (Paul Wesley), in command of the USS Farragut, was also part of this battle, which resulted in a decades-long war with the Romulan Star Empire.
4 The Gorn Captain
Star Trek: The Original Series Season 1, Episode 18 — "Arena"
While many of the enemies on this list engaged Captain Kirk in a battle of wits, the Gorn Captain takes on Kirk in hand-to-hand combat. When powerful beings known as the Metrons force Kirk and the Gorn Captain to fight to the death, Kirk must use every resource at his disposal to defeat the much stronger Gorn. Stranded on a barren asteroid, Kirk cannot rely on his crew for help and does not know how to communicate with the Gorn.

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The Gorn Captain is not only strong but also intelligent, setting a trap for Kirk using materials he finds on the planet. Kirk eventually constructs a makeshift cannon, severely wounding the Gorn, but refusing to kill him after learning that the Gorn were merely defending their territory. Kirk's mercy impresses the Metrons, who send both the Enterprise and the Gorn ship back to their respective areas of space.
3 General Chang (Christopher Plummer)
Star Trek VI: The Undiscovered Country
In Star Trek VI: The Undiscovered Country, the Shakespeare-spouting General Chang serves as chief of staff for the Klingon Chancellor Gorkon (David Warner). Chang ultimately betrays his Chancellor, plotting an assassination for which he attempts to frame Captain Kirk and Dr. McCoy. Kirk and McCoy were sentenced to life in prison on the ice world of Rura Penthe, where Chang tried to have them killed. Thankfully, Spock had undertaken his own investigation into the charges and later rescued Kirk and McCoy.
General Chang was also the first bald Klingon seen in Star Trek.
Chang continued trying to sabotage the peace talks between the Klingons and the Federation, plotting with Klingon, Romulan, and Federation officers. Although Chang's ship dealt considerable damage to the Enterprise, Kirk's ship emerged victorious in the end — with some assistance from Captain Hikaru Sulu (George Takei) and the USS Excelsior. With Christopher Plummer's gravitas and an intimidating eye patch, General Chang proved to be a particularly memorable villain.
2 Commander Kruge (Christopher Lloyd)
Star Trek III: The Search For Spock
In Star Trek III: The Search for Spock, the ruthless Klingon Commander Kruge set out to obtain information about the Genesis Device first introduced in Star Trek II: The Wrath of Khan. Although Dr. Carol Marcus (Bibi Besch) had never intended the device to be used as a weapon, Kruge sees it as a way to destroy an entire planet. Kruge eventually finds his way to the Genesis Planet, where he encounters Kirk's son, David Marcus (Merritt Butrick), along with Lt. Saavik (Robin Curtis) and a resurrected Spock.

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When iral Kirk arrives, the understaffed Enterprise engages with Kruge's Bird-of-Prey. When Kirk refuses to surrender, Kruge orders his men to kill one of the hostages on the planet, and they kill Kirk's son, David. Kirk pretends to surrender but sets the Enterprise to self-destruct before the Klingons board. With his son dead and his beloved ship destroyed, Kirk battles Kruge, ultimately watching the Klingon fall to his death.
1 Khan Noonien Singh (Ricardo Montalbán)
Star Trek: The Original Series Season 1, Episode 22 — "Space Seed" & Star Trek II: The Wrath Of Khan
In J.J. Abrams' Star Trek Into Darkness, Ambassador Spock called Khan "the most dangerous adversary the Enterprise ever faced." While this may be a slight exaggeration considering the various god-like beings Kirk and his crew went up against, Khan certainly left quite an impression. Kirk first meets Khan in "Space Seed" when the Enterprise encounters the SS Botany Bay drifting in space with the cryogenically frozen Khan and his followers onboard. After Khan nearly takes control of the Enterprise, Kirk strands him and his people on the inhospitable Ceti Alpha V.
Khan and his people were genetically engineered augments from the 20th century who possessed enhanced strength, speed, and intellect.
Star Trek II: The Wrath of Khan, seeking vengeance against Captain Kirk. Kirk is able to outmaneuver Khan in a space battle, but ultimately loses Spock when the Vulcan sacrifices himself to save the Enterprise from the Genesis Device explosion. Kirk and his crew later restore Spock's life, but the fact that Khan dealt such a devastating blow makes him Kirk's greatest Star Trek enemy.

Star Trek: The Original Series
- Release Date
- September 8, 1966
- Network
- Paramount
- Showrunner
- Gene Roddenberry
Cast
- James T. Kirk
- Spock
- Directors
- Gene Roddenberry
- Writers
- Gene Roddenberry
- Franchise(s)
- Star Trek
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