Space is the final frontier. The United Federation of Planets boldly explores uncharted regions of space in state of the art starships captained by some of the best and brightest in the fleet. Captain Archer was celebrated for being one of the first Starfleet Captains to explore the unknown on a ship named Enterprise. Captain Kirk was the stuff of legend due to his charisma and leadership. Captain Picard was revered for his diplomacy. Captain Sisko was owed a debt for keeping the Alpha Quadrant safe from the Dominion. Captain Janeway was hailed as a hero for bringing her crew back to the Alpha Quadrant after a 70,000 light year journey. However, what if we told you these famous heroes had terrible flaws?

For every great thing these Captains accomplished, there's something terribly bad they did as well. In the Star Trek universe, there are such wonderful villains as The Borg Queen, Professor Moriarty, Khan Noonien Singh and Gul Dukat, but isn't it worse when the villainy is committed by the heroes that we love? You may eagerly celebrate Captain Picard Day on June 16th, but will you forget the day that Picard shot at innocent aliens? Kirk may have saved the galaxy numerous times, but do you remember when he let a whole planet starve? Kirk was also a tactical genius, but do you remember the time when he left advanced technology in the hands of a pre-warp society? After reading this list, you may want to send some of Starfleet's most famous Captains back to the academy to re-learn the basics.

20 KIRK: ABANDONED KHAN

Star Trek II: The Wrath of Khan is arguably the best Trek film ever made, but before the film premiered in 1982, the Original Series episode "Space Seed" aired in 1967, which featured the first meeting between Captain James Tiberius Kirk and Khan Noonien Singh.

Khan tried to take over the Enterprise, but was foiled. What is Khan's punishment? Kirk puts Khan and his followers on the planet Ceti Alpha V to see if he could "tame" the planet. Hey, Kirk, wasn't Khan a genocidal maniac from the 20th century Eugenics Wars? Talk about being rewarded for bad behavior!

19 SISKO: TRICKS ROMULANS INTO JOINING WAR WITH DOMINION

One of the things that set Deep Space Nine apart from the other Star Trek series was the usage of long story arcs. The Dominion War took up most of the series, featuring the Federation's fight against the Changelings, Jem'Hadar, and other members of the Dominion.

Desperate for help, Sisko and the the former Cardassian spy, Garak, faked data in order to trick the Romulans into joining the war. It's not an honorable Federation thing to do, and fans were left with the knowledge that the Emissary to the Bajorans had to get his hands dirty. Very dirty.

18 PICARD: REPAIRED DAMAGED DRONE, LET HIM GO TO THE BORG

Is there a Star Trek villain more intimidating than the Borg? The virtually unstoppable race of cybernetic aliens first premiered in the Next Generation episode "Q Who?" Picard and his crew were desperate to find a defense against the Borg.

In the episode "I, Hugh" the Enterprise found a wounded Borg. Because they're members of the Federation, Picard does the humane thing by nursing the drone back to health, returning him to the collective, and deciding not to load into his head a computer virus that could shut down the Borg for good. Apparently, getting assimilated didn't teach Picard anything!

17 JANEWAY: STRANDED CREW IN DELTA QUADRANT

Star Trek: Voyager featured the adventures of Captain Janeway and her crew as they attempted to travel 70,000 light years from the Delta Quadrant to the Alpha Quadrant. Was the reason for the show a byproduct of Janeway's biggest mistake?

Voyager was stranded in the Delta Quadrant due to the actions of an alien known as the Caretaker. Having Voyager return home would have meant a race called the Ocampans would probably perish. Janeway's decision to save the aliens winds up stranding her crew in uncharted space. A good/bad example of Federation morality at play!

16 KIRK: LET KLINGONS POISON GRAIN HE WAS SUPPOSED TO PROTECT

The Original Series episode "The Trouble With Tribbles" is a fun episode that culminated with Captain Kirk being pelted with furry life forms. The show begins with Kirk assigned to guard a special grain that will feed people in need.

Although the image is iconic of Kirk swamped in a sea of Tribbles, this moment is actually quite grim. Not only did Kirk fail to protect the grain, he prevented a Klingon agent from tainting it, resulting in all of the Tribbles being poisoned. Also, does that mean Sherman's Planet didn't get the food they desperately needed? You had one job, Kirk!

15 KELVINVERSE KIRK: LET SCOTTY QUIT, MADE CHEKOV ENGINEER

Star Trek Into Darkness did well enough financially at the box office, but had mixed reviews from die hard Trekkies and Trekkers. In the film, Kirk wants to track down John Harrrison (ahem, Khan) to avenge the assassination of Admiral Pike, and butts heads along the way with his trusted crew.

After a disagreement with Kirk, Scotty resigns. Not only was it a mistake for Kirk to let the best engineer in Starfleet go, he replaced him with Chekov because he was "shadowing Scotty" in Engineering. C'mon, Kirk, you should know the chain of command better than that!

14 ARCHER: RAIDED A SHIP TO STEAL PARTS TO FIX THE ENTERPRISE

The Federation may be known for its strict moral code, but what did Starfleet officers do before the United Federation of Planets was created in 2161? For Captain Jonathan Archer and the crew of the Enterprise, they had to wing it without such things as the Prime Directive.

In the episode "Damage" the Enterprise needs a replacement warp coil after an attack by the Xindi. Unfortunately, Archer's only option is to steal it from a nearby ship after they refuse to trade for it. Sorry, Archer, but Picard would have been able to negotiate a trade with no problem.

13 SISKO: PUNCHED Q IN THE FACE

When you're omnipotent, you can do anything. Just ask Q. The powerful entity known as Q made multiple appearances on Next Generation and Voyager, but only showed up once on Deep Space Nine, and there's a specific reason for that.

Q appeared on Deep Space Nine and engaged in his normal verbal torture of the people around him. Unlike Picard and Janeway, Sisko had enough and punched Q in the nose. Who was more shocked: Q or the audience? Hey, Sisko, maybe it's not a good idea to punch an incredibly powerful extra-dimensional being in the kisser.

12 PIKE: ADMITS HE DOESN'T LIKE WOMEN ON BRIDGE OF HIS SHIP

If Star Trek creator Gene Roddenberry had his way, Christopher Pike would have been the Captain of the Enterprise. NBC rejected the pilot episode for being too cerebral, but by scrapping it, they had a chance to undo one of Pike's biggest errors.

While on the Bridge, Pike is handed a report by a woman and gives her shade. When asked why, he says that he has to get used to having a woman on the Bridge. First off, he's saying this to his first officer, who is a woman. Secondly, you're ok with aliens on your bridge but not women? Glad to see you go, Pike!

11 GEORGIOU: LOOKED WEAK IN FRONT OF THE KLINGONS

Being a Captain on a starship means you're a tactician, a scientist as well as a diplomat. Having to deal with alien races is no easy task, requiring you to know when to talk and when to fight. For Captain Georgiou, her biggest mistake was her last mistake.

On Star Trek: Discovery, Georgiou's First Officer, Michael Burnham, warned her Captain about encountering the Klingons. She said that Vulcans earned respect from the Klingons by firing on them at first encounters. Georgiou opts for diplomacy instead, which results in the Klingons attacking her ship.

10 ARCHER: BROUGHT HIS PET BEAGLE ABOARD A STARSHIP

Characters on Star Trek have encountered a variety of amazing and dangerous things, such as time loops, shape-shifting aliens and planet-destroying space ships to name a few. Surviving in space requires courage, strength and determination. That being said, what hope does a beagle have surviving in space aboard the Federation's prototype Warp 5 vessel?

Porthos was the pet of Captain Archer. Wouldn't Archer be worried every time the ship shook violently due to being pelted by weapons fire? Would alien races think Porthos was the Captain's slave? Archer, leave your pets at home and focus on your crew!

9 KIRK: LEFT STARFLEET EQUIPMENT ON TECHNOLOGICALLY INFERIOR PLANET

Strange, new worlds can sometimes be just that. Kirk and his crew went to the planet Sigma Iotia II, only to find the aliens were living in a society that mirrored gangster culture on Earth in the 1920s. Kirk and Spock infiltrated the Iotian society by wearing some awesome pinstripe suits.

At the end of the episode, McCoy revealed that he accidentally left his communicator on the planet. Instead of turning the ship around and beaming it up (an action that would take seconds to do), Kirk decides to leave advanced Federation technology with the Iotians. Hey, Kirk, the communicator isn't an iPhone!

8 PICARD: DROVE DUNE BUGGY AND FIRED ON INNOCENT ALIENS

Where do we begin with the problems of Star Trek: Nemesis, the film that arguably killed off the Next Generation franchise? Let's start with the Enterprise discovering a positronic signal from an inhabited planet near the Romulan Neutral Zone. On the planet, they discover a third Soong-type android that they name B-4.

The landing party is attacked by the pre-warp species indigenous to the planet. Do the crew beam away before things escalate? No, Picard drives the crew away in a dune buggy while Worf fires on the aliens who are just trying to defend their home against intruders. Jean-Luc, not every day can be Captain Picard Day.

7 HARRIMAN: LET KIRK TAKE COMMAND OF HIS VESSEL

If you're a crew member on a starship, the Captain is someone that you can look up to in a time of crisis. Starfleet Captains are supposed to stay cool under fire and be an inspiration to those around them. And then there's Captain Harriman.

Captain Kirk is present for the inaugural launch of the Enterprise B, captained by Harriman. There's a distress call, and due to the ship being ill-equipped, Harriman immediately asks Kirk for help. You've been chosen to carry on the Enterprise legacy and you're telling us you don't know how to handle a simple distress call?

6 LORCA: PUT TOO MUCH TRUST IN TYLER ASH

Captain Lorca of the U.S.S. Discovery seemed at first to be a good judge of character. Even though Michael Burnham was a convicted felon, he knew that she would be of great use serving aboard the Discovery. Lorca then dropped the ball when he met Ash Tyler.

Lorca was held in a Klingon prison but was freed alongside his cellmate, a man named Ash Tyler. Almost immediately, Tyler was made Lorca's new Chief of Security, only to find out later that Tyler was actually a Klingon in disguise. Audiences also found out later that Lorca was from the Mirror Universe. Is everyone in disguise?

5 KIRK: FOUGHT SPOCK TO THE DEATH

Vulcans are a logical, dispassionate people, but like all living things they have a need to eat, sleep and mate. Every seven years, Spock and other Vulcans go through Pon Farr, which is Vulcan for mate or die. Yes, Vulcans will die in about a week if they don't Vulcan grip some booty.

The woman that Spock wants to get with evokes a law that makes Spock fight for the right to be with her. Kirk is the one chosen to fight Spock. Kirk volunteers without finding out more information, and learns that it's a fight to the death. Bad choice, Captain, Spock won't lose when there's Vulcan women at stake.

4 PICARD: RAMMED THE ENTERPRISE INTO AN ENEMY SHIP

Star Trek: Nemesis featured Captain Picard fighting his clone. Picard was in command of the Enterprise E and his clone, Shinzon, skippered a gigantic warship named the Scimitar. The Scimitar could fire while cloaked, and even when fighting alongside other Romulan vessels the Enterprise was outgunned.

Picard, the tactical genius that created what would be later known as the Picard Maneuver, had to come up with a way to do significant damage to the enemy vessel. Picard surprises Shinzon by ramming the Enterprise into the Scimitar... and that's it. Normally ramming is followed by boarding parties, but that was it for Picard's "bold" move.

3 JANEWAY: EXPOSED ADVANCED FEDERATION TECHNOLOGY TO THE BORG

Janeway was certainly haunted by her decision to strand U.S.S. Voyager in the Delta Quadrant. In the episode "Endgame" we learn that it took Voyager 23 years to travel back to the Alpha Quadrant. Now a Vice Admiral, Janeway vowed to find a way to right the wrongs she committed.

Janeway stole several pieces of technology and brought it back to the past to help Voyager and her crew. Voyager, armed with transphasic torpedoes and ablative armor, was able to resist virtually everything the Borg threw at it. The bad news? The Borg now know of this future technology and can adapt to it.

2 SISKO: USED BIOLOGICAL WARFARE AGAINST HUMAN COLONISTS

Besides having to deal with the Dominion War, the crew of the Deep Space Nine also were grappling with the threat of the Maquis, an anti-Cardassian resistance group. Michael Eddington, a security officer on Deep Space Nine, was revealed to be a member of the Maquis.

Sisko had the chance to track down Eddington, who had been able to evade Sisko on numerous occasions. Fed up, Sisko attacked a Maquis colony by polluting their planet's atmosphere with trilithium resin. Eddington was forced to surrender himself to protect the other colonies. When did Sisko decide he was The Punisher?

1 KIRK & PICARD: LEFT THE NEXUS AT A TIME THAT OFFERED NO TACTICAL ADVANTAGE

The film Star Trek: Generations brought together Captains Kirk and Picard in a realm known as the Nexus. If you're able to get to the Nexus, you're granted whatever you desire. Time also has no meaning here, so you can live in your own personal paradise forever.

Kirk and Picard find themselves in the Nexus and decide to leave to fight the evil Doctor Soran. Because time has no meaning, they could exit the Nexus at literally any point in time. They could have left when Picard first met Soran or days before Kirk perished on the Enterprise B. Instead they leave after the Enterprise D was destroyed. Oops!