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Hi I'm not sure of the exact meaning of this sentence:

You may not engage in private practice or be connected with any outside business which would interfere with the performance of official duties.

Can I read this as meaning I CAN engage in private practice provided it DOES NOT interfere with the performance of official duties.?

As in You may not (engage in private practice OR be connected with any outside business) which would interfere with the performance of official duties.

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    This is not in English but in the foreign language known as legalese. You should consequently consult the regulating entity who wrote that, or barring them, a lawyer. – tchrist Sep 25 '16 at 17:27
  • Thanks. I did ask in plain English and was referred to the above text – KevInSol Sep 25 '16 at 17:34
  • @KevInSol: The text itself is inherently ambiguous, so any opinions expressed here would be just that. Off-topic opinions. – FumbleFingers Sep 25 '16 at 17:43
  • @tchrist Any lawyer worth his/her salt would have added an "and", as in "...private practice AND/OR be connected with...". That's the way to do it. – Peter Point Sep 25 '16 at 18:28
  • @PeterPoint: I don’t see how your suggested rewrite resolves the ambiguity in the text. – Scott Sep 26 '16 at 4:47
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The sentence in question—

You may not engage in private practice or be connected with any outside business which would interfere with the performance of official duties.

—has two levels of ambiguity:

  1. Does "which would interfere with the performance of official duties" apply both to "You may not engage in private practice" and to "[You may not] be connected with any outside business," or does it apply only to "[You may not] be connected with any outside business"?

  2. Does "which would interfere with the performance of official duties" apply restrictively or nonrestrictively to the antecedent or antecedents that it applies to?

As these two questions suggest, four more-or-less defensible readings of the original sentence are possible:

  • Reading 1: The "which" clause is restrictive and applies to both antecedents.

  • Reading 2: The "which" clause is restrictive and applies only to the second antecedent.

  • Reading 3: The "which" clause is nonrestrictive and applies to both antecedents.

  • Reading 4: The "which" clause is nonrestrictive and applies only to the second antecedent.

Now let's consider how we might alter the original sentence in order to convey, unambiguously and in turn, each of the four possible meanings outlined above. Using U.S. punctuation and style conventions, we might accomplish that goal as follows:

  • Reading 1: "You may not engage in private practice if doing so would interfere with the performance of official duties, and you may not be connected with any outside business if maintaining such a connection would interfere with the performance of official duties."

  • Reading 2: "You may not engage in private practice, and you may not be connected with any outside business that would interfere with the performance of official duties."

  • Reading 3: "You may neither engage in private practice nor be connected with any outside business, because either action would interfere with the performance of official duties."

  • Reading 4: "You may not engage in private practice; and furthermore, you may not be connected with any outside business, because the latter arrangement would interfere with the performance of official duties."

As you can see, the original sentence doesn't look terribly similar to any of those four formulations. That is because it—unlike them—is arguably ambiguous (arguably by a competent and dedicated lawyer, that is). It simply isn't beyond question that the writer of the sentence intended "which would interfere with the performance of official duties" to apply only to the second antecedent clause, nor is it beyond question that the "which is intended restrictively rather than nonrestrictively. The stage is set for multiple rounds of "the lawyers win and all their clients lose."

From his comments in the posted question, I gather that the OP would like to interpret the original sentence in accordance with Reading 1. A lawyer could certainly make such a case—but in my view the least tortured interpretation of the original wording favors what I have called Reading 2, which amounts to saying the following:

You may not (1) engage in private practice or (2) be connected with any outside business that would interfere with the performance of official duties.

This reading does little violence to the original wording (beyond replacing which with that, and inserting parenthetical numbers to fully separate the two prohibitions that the sentence seeks to impose), and it interprets that wording unambiguously and in good faith. But I made that assessment as a reader trying to make sense of an imperfectly framed statement, not as a lawyer trying to win a case for my client. In the adversary system of law, what matters most to an advocate isn't which interpretation is most reasonable, but rather which argument gives one's client the best prospect of persuading the jury (or judge).

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That's an extremely dangerous sentence, even if it does come from an enacted law.

The real meaning of anything like "You may not engage in private practice or be connected with any outside business which would interfere with the performance of official duties" is moot and it is also one of the reasons why - in Britain, anyway - lawyers loathe and abhor commas.

To shorten the sentence for clarity, "engage in private practice nor be connected…" would fairly clearly separate the phrases on each side of “nor”. That would make “…which would interfere with the performance of official duties" subordinate to the second and not to the first, but “fairly” is the operative word, not “clearly”.

"engage in private practice or be connected…" might then be seen as the opposite, combining rather than separating the phrases but it need not be.

Could the issue be resolved by saying “neither engage in private practice nor…”?

Whatever grammarians, linguists or anyone else might think, a question like that will only ever be resolved by a judge, or a panel of judges and whether any of them understands or agrees with what you or I think might not matter any more than what colour socks they happen to wearing on the day…

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You may not engage in private practice or be connected with any outside business which would interfere with the performance of official duties.

This sentence is ambiguous. The antecedent of "which" could be "business" alone, or both "business" and "practice". Ambiguous syntax is ubiquitous in English; it's bad to include it in legal contexts where context doesn't disambiguate, but people don't always realize when this occurs.

As others have mentioned, because it is ambiguous in natural language, the correct legal interpretation will have to be based on legal concepts, rather than or at least in addition to linguistic concepts.

Others have suggested alternate wordings with dubious value at disambiguating the referent of the relative clause. Frankly, I think attempting to make an "any" or "nor" or "and/or" carry this meaning is dangerous. I would advise anyone writing sentences like this in legal contexts to replace them with lists instead.

You may not do any of the following activities if it would interfere with the performance of official duties:

  • engage in private practice
  • be connected with any outside business

Or

You may not do any of the following activities:

  • engage in private practice
  • be connected with any outside business that would interfere with the performance of official duties
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IMHO, your interpretation contradicts the plain meaning of the text. If they wanted to allow private practice that does not interfere with the performance of official duties, they would have written (at least):

You may not engage in any private practice or be connected with any outside business which would interfere with the performance of official duties.

There is also the matter of using which vs. that which I won't go into here.

  • I’m confused. (1) I don’t see how the “plain meaning rule” resolves the ambiguity in the text.  (2) I believe that your suggested rewrite has the opposite meaning of what you say it means. – Scott Sep 26 '16 at 4:47
  • @Scott (1) There s no ambiguity when you read the text plainly, without twisting it to suit your purpose. (2) I don't think so. But I do agree that it is ambiguous. – michael.hor257k Sep 26 '16 at 7:40
  • What does “Don’t consume any food or beverage that smells bad” mean? (1) Don’t eat any food at all.  Also, don’t drink any beverage that smells bad. (2) Don’t eat any food that smells bad.  Don’t drink any beverage that smells bad.  —  The plain meaning is #2. Do you agree? The OP is interpreting an analogous construction the same way — why do you say he is twisting it? – Scott Sep 26 '16 at 7:59
  • @Scott Plain meaning also takes context into consideration. Note also that you have used that, not which, If you had written “Do not consume food or any beverage which smells bad” then I would not agree with you - esp. if the context allowed for total abstinence from eating. – michael.hor257k Sep 26 '16 at 8:11
  • @Scott See also what happens when you remove the second clause: you end up with a completely contrived "You may not engage in private practice which would interfere with the performance of official duties." OTOH, "You may not be connected with any outside business which would interfere with the performance of official duties" is perfectly natural. – michael.hor257k Sep 26 '16 at 8:15

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