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The Prime Directive is Starfleet's general order number one regarding contact with new forms of life - as a rule, captains are not supposed to violate it, yet often they're forced into situations where they do.

As a result, when Captain Picard was brought to trial on drummed-up charges, he was accused of violating the prime directive a total of 9 times.

SATIE: Would it surprise you to learn that you have violated the Prime Directive a total of nine times since you took command of the Enterprise? I must say, Captain, it surprised the hell out of me.

Episode Transcript - 'The Drumhead'

I can think of at least two instances where Picard violated the prime directive on-screen. One was in Who Watches the Watchers where he accidentally became a godlike being to a primitive race, and another in First Contact (Not the movie) where it was Riker who was found out, and forced Picard to make contact with the new civilization prematurely.

Were there in fact seven other on-screen instances of Picard violating the prime directive before this episode? Or are we meant to assume a number of them happened off-screen?

  • 9
    The answer is loads. At least once per season. – Valorum Jan 21 '15 at 23:27
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    Discussed here, at considerable length. . Feel free to review and decide whether to answer the question yourself. – Valorum Jan 21 '15 at 23:29
  • The Prime Directive is violated every time someone behaves intelligently. – EvilSnack May 18 '18 at 5:04
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The Memory Alpha page on the Prime Directive lists several examples of Picard violating the Prime Directive. Note that for this answer, the Prime Directive will be interpreted in its most absolute form i.e. there being no exceptions to it - pre-warp civilizations must not be contacted.

  • 'Pen Pals': Picard declared that the distress message from Drema IV was sufficient grounds for an exception to the Prime Directive. Despite the precautionary measures taken, this still does count as a violation.
  • Nemesis: when investigating positronic signatures, the pre-warp civilization of Kolarus III were exposed to Federation technology and Federation personnel, thereby culturally contaminating them.

Arguably:

  • 'Who Watches the Watchers': the Enterprise-D was involved in the cultural contamination of the proto-Vulcan society. It wasn't Picard's fault that the holographic projector failed, but subsequent efforts to minimise cultural contamination didn't help matters, so it could be said here that Picard violated an absolute interpretation of the Prime Directive
  • 'Homeward': Transportation of the pre-warp society of Boraal II. Again, this wasn't technically Picard's fault, but his decision to resettle the society elsewhere could also be seen as violation of the Prime Directive.
  • 'Justice': Picard's interference in the justice system of the Edo society of Rubicun III

So that's five times we see it on screen, but several of these, notably Nemesis and 'Homeward' hadn't even occurred prior to 'Drumhead'.

The article which @Richard refers to lists several other possibilities:

Debatable:

  • "Angel One": The away team, ultimately Picard's responsibility, gets pretty close to the line of interfering with the society of Angel I by encouraging its more egalitarian elements.

  • "Symbiosis": Picard withholds basic assistance from a pair of space faring races to break a cycle of addiction. His unconventional inaction could be seen as a form of interference.

  • "The Hunted": Similar to "Symbiosis", the presence of the Enterprise facilitates certain events (the escape and recapture of Roga Danar) that Picard later deliberately interrupts to be nominally "non-interfering" but in actuality to achieve the result he desires (change in the Angosian government).

  • "The High Ground": Picard and the Enterprise crew become more entangled than they intended in the Rutian civil war.

  • "Devil's Due": While "Ardra" was a phony, Picard could be considered to have over-involved himself in the "spiritual" evolution of the Ventaxians by challenging her authority.

  • "First Contact": When does a fouled up first contact situation become cultural interference?

Stretching it:

  • "Code of Honor": When your security chief ends up in a fight to the death with the mate of the leader of an alien world, it doesn't look good on the report.

  • "Reunion": Arbitrating the future leadership of the Klingon Empire is not exactly Starfleet's idea of a captain's role.

  • "Transfigurations": An even more incidental effect of the Enterprise going about its normal business, yet still playing a part in massive societal change.

So, if you were to accept all of these (and quite frankly even I don't accept all of these), it would amount to 14 times on screen we see Picard violating the Prime Directive.

Regarding what is said in 'The Drumhead', of the above cases, 'Pen Pals', 'Who Watches the Watchers', 'Justice', 'Angel One', 'Symbiosis', 'The Hunted', 'The High Ground', 'Devil's Due', 'First Contact', 'Code of Honor', 'Reunion' and 'Transfigurations' are all set prior to 'The Drumhead', making 12 possible violations of the Prime Directive shown on screen prior to 'The Drumhead'. Hence, assuming the only violations of the Prime Directive occurred on screen, then three of those 12 must not be considered violations by Starfleet.

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    "Devil's Due" in particular is pretty blatant: Ardra's claim on the Enterprise is extraordinarily weak. She claims the Ventaxians essentially sold it to her, but they never owned it to begin with. Under a strict interpretation of the PD, Picard should have called her on this, and then left. – Kevin Sep 21 '15 at 2:32
  • @Kevin I think I disagree with you on Devil's due because that planet already had relations with the federation, that was why the enterprise received a distress call from federation members on the planet's surface (who were later taken prisoner and freed by Ardra's request). Already having a relation means, to me, that the federation providing assistance wasn't a violation. But as so many have said, interpretation is individual. – userLTK Dec 5 '16 at 22:34
  • @userLTK: Perhaps. But the fact that nobody pointed out this blatant hole in Ardra's reasoning still annoys the hell out of me. – Kevin Dec 6 '16 at 0:34
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    @Kevin I agree with you there. Two other things that bother me. Ardra (the con artist) should want Picard to leave as she should be smart enough to perceive him as a threat, but that could be written off as overconfidence. A 2nd, I find it odd that Arda's little ship with an old cloaking device could block the enterprise transporters without being detected. But maybe a very strong magnetic field on the planet made her ship hard to see, so, OK, maybe. Your legal objection is valid. I agree with you there. The episode was still fun (IMHO) but it had flaws. – userLTK Dec 6 '16 at 4:40
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In my mind, Picard did not really break the Prime Directive in all cases.
That's why Starfleet Command did not take his command.

Symbiosis f.e.
If the Enterprise would not have interfered in the first place by saving the travelers, the end result would be the same. They could not longer sustain the transportation of the drug. So no real violation here. (the same concept aplies to "The Hunted")

In the episode Justice, the planets "leader" was the godlike presence in orbit and it allowed the away team to beam up with Wesley. The highest authority gave his consent. (Because it realized the unfairness regarding this incident)

In Who watches the Watchers, the damage was already done by the research team. It was exposed by the time the Enterprise arrived. Beverly just fulfilled her medical duty by helping Palmer, who had also already discovered the research station, when the away team beamed down. (And picard was not very fond of it...)

I have more examples.

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