John Saxon as John Flagg, drawn by Richard Spake


John Flagg as Portrayed by Bruce Payne. Photomanip by Unknown

John Flagg is a character in ST-OM

Sources Edit

Warning. This article contains links to Wikipedia and TV Tropes

John Flagg was inspired by the M*A*S*H character Sam Flagg

Some inspiration may have come from the real life figures of Otto Skorzeny and G. Gordon Liddy

Originally a vehicle for semi-humorous commentary on nationalism, patriotism and paranoia, Flagg has become a much darker and villainous character.

Flagg feels that The Federation is the Utopia that justifies the means

Flagg is a Well Intentioned Extremist who feels that galatic politics is a dirty business and that he is a man who Does What He Has To Do

Flagg does not really understand ethics or morality. He is a sociopath who has transfered his loyalty, personal identification and self esteem onto the abstract notion of the Federation.

The Federation is founded on the idea of having a principled, ethical government. So for Flagg to committ unethical acts to advance the Federation is a violation of the Federations reason for existing in the first place.

Flagg dismisses this as propaganda. In his mind, Ethics and Principles are slogans for keeping the civilians of the Federation in happy ignorance. Flagg feels that most people are too emotionally and mentally weak to do What Has To Be Done. He sees himself as a strong person who can defend the Federation and help the Federation win the Great Game


Flagg is an excellent martial artist and warrior.

He is an excellent infiltrator, using skills of both phsyical thievery and data penetration to access forbidden data in dangerous locations.

He is a very good strategist and tactician.

Flagg is an excellent con-man and observer of humanoid nature. He can identify personal weaknesses with uncanny accuracy, and manipulate people into positions and actions that they would have never considered otherwise.

Flagg is a good Chess Master with a flair for the Xanatos Gambit.

However Flagg's true strength lies in situational improvisation and his ability to descend to frightenly ruthless methods, more quickly and directly than anyone expects.


Flagg really doesn't understand ethics. He'd cheerfully set his own mother up to be captured and interrogated by the Obsidian Order to advance his mission goals.

Flagg defines himself by whatever mission he is pursuing, using this as a frame to constuct his plans and goals.

Flagg secretly believes that in time the Federation will come to understand the necessity and benefit of his actions, and properly regard him as a hero. Subconsciously Flagg craves approval and love from the Federation. As Flagg is jailed, resisted and punished for his actions by the Federation he is slowly going mad.


People who know John Flagg see him as a dangerously violent lunatic who is liable to do horrible things for twisted reasons. While accurate, Flagg often uses this as a cover.

John Flagg operates undercover as a freelance agent and assassin in the world of Galactic Episonage. He has a secretive patron inside Starfleet Command. His patron shares his ruthlessly pragmatic view of Federation foreign policy. Although Flagg's persona is that of a freelance actor, this is a cover. Flagg has undertaken immoral and criminal jobs in order to forward the image that he is no longer a Federation agent. He rationalizes these actions as being necessary for the long-term greater good of the Federation.

Flagg has numerous contacts in the underworld of known space. He is a good source for information, money and to contract denial jobs if a criminal is paranoid enough to properly cover his rear end. Flagg will happily hijack or betray criminal organizations to forward his own agenda.

Usually, Flagg is just moving through, conducting business with acquaintences while engaged in another project. Flagg maintains deniability and if necessary will kill witnesses to keep a full picture of himself and his operations out of Orion hands.


John Flagg is a wanted criminal according the United Federation of Planets. However, Flaggs extensive knowledge of Federation intelligence services and methods have allowed him to break into Federation facilities and help himself to whatever he felt he need.

Somewhere inside Starfleet Command there is a person just as pragmatic and ammoral as John Flagg is. This person is John Flagg's patron. He uses resources available to him to tilt things in Flagg's favor, when Flagg's goals match his. This being allows Flagg access to money and resources he would not otherwise have.

Flagg, being a goood spy squirrelled away money, documents, weapons and other useful tools in his prior career. Flagg is also not shy about looting his victims for weapons, tools and money to servd his own goals.

Flagg and his patron design Flagg's activities using a parallel communications system they have added to other top secret starfleet and Federation systems


In Star Trek - Outwardly Mobile, Flagg has built Ekos up into a competent if small stellar nation on the galactic stage. Flagg and his patron desired a maleable buffer state to use as a deniable arm of force for their operations. The Ekosian ruling council has taken Flagg up on his offer, as he has bribed them with Federation technology, money, ships and other people's planets.

Flagg has morphed into a sort of a mix of James Bond and Ahab. For Flagg, The starship USS Discovery has become a physical representation of the approval and love he seeks from the Federation, and Jay P. Hailey has become the embodiment of his rejection by the Federation.

Epiphany TrekEdit

John Flagg attempted to infiltrate the planet Oz, using his usual, violent socioathic methods. He was caught and sentenced to death by the Ane.

However a second John Flagg appeared with the Duplicate Harrier - this iteration of Flagg was given therapy by the Ane, as well as a clear view of the errors committed by the original Flagg. His world view upended and all but destroyed, this Flagg retired from Starfleet, resumed his original name of Herschel Osborne and began to re-create himself in a more sane fashion.

Herschel, fearing he was bringing destruction to his friends on Oz signed aboard a Wanderer ship and left to wander space. His current whereabouts and condition are unknown.


  • Name: John Flagg (Not the name he started with.)
  • Race: Human
  • Born: 2325
  • Birthplace: Unknown Probably Earth, location not specified.
  • Parents: Father: Otto Osbonrn -- human supremacist wastrel Flagg is known to have had a serious Love - Hate relationship with his father. The Elder Flagg was a human supremacist wastrel, and emotionally abused the Young Flagg. Flagg adopted the Federation and Starfleet as his emotional family. Flagg maniacally seeks approval and acceptance from Starfleet in a variety of unhealthy ways.
  • Siblings: None specified at this time (Flagg's evil revenge crazed brother? HELP ME!)
  • Height: 5' 9"
  • Weight: 165 lbs
  • Description: Flagg is a compact man. He has bushy black hair kept short, and dark brown almost black eyes. His body is reminiscent of Bruce Lee's with excellent muscle development and flexibility. In dress Flagg, chooses his Starfleet Uniform, carefully tailored, tended and arranged with every detail utterly perfect, or dark clothes of a somber cut, or whatever costume that is appropriate to his mission.
  • Personality: Flagg is characterized by a deep love and need of approval from the Federation, combined with an utter cluelessness about the principles behind the Federation.

    Flagg sees galacti-politics as the Great Game, centered on territory, wealth and influence and means to see that his beloved Federation wins at any cost.

    Flagg slowly, grindingly, went mad. When he makes his best efforts, and really accomplishes surprisingly effective results, his scheme turns into a disaster, with lots of disapproval from the Federation.

    Flagg doesn't understand this and the apparent inconsistency did some serious harm to his stability. Flagg hates Counselors, although he admits that they might be necessary for other people. He avoids them at all costs. Part of the madness was to see the madness as one of his strengths.

  • Skills/training/Professional Skills: Flagg is trained in all areas of Intelligence work that he can reach to some degree. Flagg is an adequate undercover agent. He is an expert martial artist and trains constantly to keep a razor's edge of readiness. Flagg is a surprisingly good hacker, and has an intuitive knowledge of how computers interrelate. Flagg is a decent intelligence analyst, but much prefers to work in the field (Adrenalin junkie.).

    Flagg has working knowledge of Orion, Klingon, Cardassian and Romulan languages, military structures and cultures. His area of expertise is in the realm of the Cardassian Union and tracking the Orion Crime Syndicate.

    Each of these areas of competence grow, change and then fade depending on how able Flagg is to keep up with the latest developments.

  • Education: Flagg graduated elementary and high school level education of Federation standard level. He did much of his high school in and out of counseling. Somehow he got though Starfleet marine training and Officer Training School without the ideals of the Federation making much impact.

Career HistoryEdit

Born: 2325

Age 10, 2335: Flagg's father is verbally abusive of Flagg and aliens everywhere. Flagg is trapped between a deep desire for his father's approval and a deep hatred of his father as a human being. Teachers are concerned.

Age 13, 2338: At a Founding Day Field Trip to Space Dock, Flagg falls in love with Starfleet, and becomes an immediate fanatic.

Age 16, 2341 police are called to the Flagg home for a domestic dispute. Flagg and his father have become violent towards each other. Flagg moves out on his own at the suggestion of counselors. Flagg Senior disowns his son and the two never speak again.

Age 18, 2343. Flagg attempts to enlists in the Starfleet Marines at 12:01 am on his birthday. Flagg is not accepted. Flagg returns to his schooling and preparation work more determined than ever.

Age 19, 2344, Flagg reapplies to Starfleet Marines is accepted, with a testimonial by his counselor. Starfleet counselors are worried about Flagg, but hope that the Marines and the ready presence of counselors can help Flagg.

At Boot Camp, Flagg starts off rocky, but his performance improves by leaps and bounds. The pattern in clear. His immediate response is brutal, direct, and very pragmatically pro-Federation, once the error is pointed out Flagg enthusiastically adopts the appropriate pro-Federation stance, and reefs on it.

Age 21, 2346, Flagg applies to the Officer Training School at the Marine Acadmey. as soon as he is eligible to do so. Due to hard work and good record he is accepted. His instructors seeing talent quickly move him to the intelligence track.

Age 23, 2349 Flagg graduates the Intelligence Officer's curriculum, near the top of his class. Flagg's Skills at Data-mining, signal analysis, and technical skills are the top of his class. Ethics professors note that Flagg repeats all answers to tests correctly and can parrot long passages from the source material, but may not truly understand what is being said. A recommendation is floated to hold Flagg back a year or to transfer him to the First-Contact/Diplomatic branch. Starfleet Intelligence ignores this and Flagg graduates on schedule.

Flagg is noted for being willing to try *anything* that a superior officer asks of him, occasionally with surprising successes and failures.

Cadet Cruise. 2350 Flagg serves at a listening post along the Cardassian Frontier.

Flagg's work is excellent but he annoys his superiors by turning in detailed analysis that support his contention of an imminent war between the UFP and the Cardassians. The UFP still hopes for a peaceful resolution. Flagg makes a pest of himself, even submitting proposed war plans and defensive stratagems. OER Good, the Commanding Officer likes Flagg's enthusiasm. Flagg graduates and is commissioned a Second Lieutenant.

First tour 1 year 2351 - Flagg serves as a data analyst at Starfleet Command, a job the threatens to bore him to death.

Second Tour 4 years, 2352 - 2356. The Cardassian War. Flagg's star is on the rise. He one a few people who said the war is coming on record. He is transferred to a Data Gathering unit on the front. Flagg's unit is combined data analysis, covert operations unit. Flagg trains with other Starfleet Marines assigned to the Unit and takes to the life of a Special Ops Officer with relish.

Cardassians complain of sentient rights violations, war crimes and unfair fighting in general and point to Starfleet Special Operations units as particular offenders.

OER Excellent. Flagg is promoted twice, to Major over the course of this campaign and decorated. Many details of Flagg's missions are classified very highly.

Third Tour 4 years 2356 - 2360. The Orion Offensive. With the Cardassian War over, Flagg and a handful of his Special Ops cronies launch an offensive against the Orion Syndicate. The early parts of this campaign involve lots of preparation and study. Flagg learns the Orion Language with some skill and learns details of Orion Culture, Smuggling and contraband trade, which he will later use to his advantage. One of Flagg's team is Enrico Watabe. They have an immediate meeting of minds.

When the Orion Offensive swings into action, the successes are not as straight forward as in the Cardassian Campaign. Bombings, assassinations, crimes, torture and a campaign of terror are not as easily covered up or dismissed as a natural side effect of war. Worse, the Orions practice these tactic among themselves and so have more well developed defense mechanisms about them. Flagg finds mission goals falling out of reach and disapproval from Starfleet command regarding his tactics.

Frustration begins to take a toll.

2359 the Halworth Incident. Flagg saw through his Orion contacts that a Federation Dissident group was acquiring weapons. Flagg saw this as a betrayal of the Federation and reacted harshly.

Launching an assault by his special ops people, Flagg and company broke up a meeting of the dissident group violently. Some Federation troops used weapons that were not set on stun. Deaths and injuries resulted.

In the aftermath, computer records showed that it was mainly the regular Marines who fired weapons set to kill. Flagg turns his back on several old comrades as they are drummed out of the Service and sent to New Zealand.

The stunned survivors of the dissident group reveals that they acquired weapons mainly as a PR stunt and bargaining ploy and had no intention whatever of violent terrorism.

Flagg is censured, and his anti-Orion group is broken up.

A rumor circulates afterwards that Flagg tampered with evidence both before and after the event to get off the hook and let his Marine Troops take the heat. Flagg's reputation with Starfleet Marines goes into negative numbers and stays there. He is considered a traitor by the Troops.

OER for Third Tour Poor.

Tour Five, Starfleet Command, seven years, 2360 - 2367 Desperate for redemption, Flagg interferes with a green Orion Girl entering Starfleet Academy. He directs her to the Intelligence Curriculum, and through

2362 - 2364 he takes a personal hand in her training to go undercover in the Orion Worlds.

Flagg acquires a patron in Starfleet Command during this time and often does special jobs for his Patron, including spying on Starfleet and Federation people, and arranging dirty tricks to foil people that Flagg and his Patron consider a threat.

Through out 2364 and 2365, Flagg and his protege Li'ira attempt to find some route inside the Orion Syndicate that will allow Li'ira to be placed in a strategic point. They are unsuccessful and suffer a couple of close calls, while generating helpful data for The Federation Justice Department.

Flagg's Patron makes of a point of disengaging Flagg from his anti-Orion activities.

Flagg begins to understand that Starship Command is essentially a prerequisite for higher rank in Starfleet. In the back of his mind he begins to look for opportunities to add this element to his resume.

In 2366, On a mission for his Patron Flagg comes across Charles Holly and is inspired. If Holly's mad science can be developed into a viable device for the Federation, then the Federation would have a big advantage, and Flagg would be the golden boy once again.

Flagg's Patron is impressed with Flagg's presentation of the potential for Holly's device Flagg is promoted to Lieutenant Colonel and given a black budget with which to develop and test the Holly Hop Drive. While the initial stages of the development are Under way Flagg and Li'ira both do Command School and get Ship's Masters Tickets, the technical requirement to be Starship Command Staff.

In 2366/67 the Borg attack at Wolf 359 rattled Starfleet badly. Among some of the side effects were uncertainty about the Cardassian response. Flagg's Patron had him split his time between the project to refit the USS Harrier for the full scale Holly Hop test, and trips out to the Cardassian Frontier to develop information and make contact with Cardassian High Command. Flagg develops some of the data that leads to the events in "TNG: Chain of Command".

In June 2367, While Flagg is out making covert contact with Cardassian High Command, the Holly Hop test goes ahead without him under mysterious circumstances. A duplicate of Flagg is involved somehow. The test fails thoroughly revealing serious flaws in Holly's mad science. Flagg loses his protege to front line starship duty, and all his effort into the Holly Hop is wasted.

However Flagg's Patron is pleased with his performance at the Cardassian Frontier and Flagg is promoted to Full Colonel with promises of more opportunities to make his mark as time goes on. OER Excellent, promoted to Colonel.

Duplicate FlaggEdit

John Flagg is duplicated like everything else on the USS Harrier. He comes to a much different end. (unfinished.)

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