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The man wasn't very trustworthy. On the contrary, he had been caught stealing twice from his boss.

The above sentence seems incorrect to me, as far as I know, the use of on the contrary is for denying/contradicting, but in this sentence both parts are giving the same negative thought about person. So the use of on the contrary doesn't seem to be fitting there. Any explanation is highly welcome.

  • I used to be puzzled by On the contrary when I encountered it as a child. But it is indeed usually used not to contradict the previous statement, but to confirm or intensify the (negative) previous statement. – Colin Fine May 14 at 9:57
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From Merriam-Webster's definition of contrary:

on the contrary
: just the opposite
// The test will not be easy; on the contrary, it will be extremely difficult.

What the phrase does is contradict a claim within the previous clause:

The test will not be easy.
→ The test will be just the opposite of easy.


The phrase doesn't contradict the entire previous sentence or clause, but only one simple fact within it:

The test will not be easy. On the contrary, (of the test not being easy) it will be extremely difficult.

✔ The test will not be easy. On the contrary, (of easy) it will be extremely difficult.


So, in the example sentence in the question, it is contradicting the trustworthiness of the man:

The man wasn't very trustworthy. The man was just the opposite of trustworthy [because] he had been caught stealing twice from his boss.

The man wasn't very trustworthy. On the contrary, (of trustworthy) he had been caught stealing twice from his boss.

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I agree with you: it doesn't seem like the best fit here. That's because I also interpreted 'on the contrary' to contrast the entire previous sentence, but I think it's only intended to contrast '(not) trustworthy'. However, it is correct.

Perhaps it's not the best structure by the author. I would propose:

The man wasn't very trustworthy. In fact, he had been caught stealing twice from his boss.

Or, if we are determined to keep 'on the contrary', we might change the adjective:

The man was far from honest. On the contrary, he had been caught stealing twice from his boss.

Your understanding that 'on the contrary' is used for contradiction is perfectly correct.

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  • I have to disagree that the phrase is used for contradition, as does the dictionary. You don't contradict yourself. The dictionary says it is for emphasis. – Astralbee May 14 at 9:31
  • I wouldn't say you contradict yourself, no, but rather a term. Maybe contradiction is too strong, and denial of a previous statement is better. "Is he trustworthy? On the contrary, he's completely untrustworthy" – JMB May 14 at 14:03
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It is correct. Remember, when you say "on the contrary", you're not contradicting yourself! So both your statements have to be true.

The phrase "on the contrary" is in the dictionary, and one definition is:

used to intensify a denial of what has just been implied or stated by suggesting that the opposite is the case.

It is correct then that the second sentence would agree with the first, as it is being used to "intensify a denial". In your example, the first statement is a denial of his trustworthiness, and the second statement backs that up by demonstrating that, on the contrary, he has proved untrustworthy.

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