If the meaning of regards is best wishes, would not best regards (used to express friendliness in greetings, especially at the end of letters) a pleonasm, in the context of letters?
Best best wishes,
I think there are two main points here:
Regards does not only, nor originally, mean best wishes. In some particular contexts — most often, as closing salutations in letters or emails — they’re indeed effectively synonymous. But regards has other meanings as well. Originally, regards carried no specific connotations of being good; it just so happened that one of its most frequent usages was for sending people kind wishes, and so in that context, it picked up those connotations.
Even if that were its only meaning, synonyms are not exact, and meaning is not substitutive — synonyms are very, very rarely so exactly synonymous that you can always substitute them for each other without changing meanings.
For instance, as synonyms go, puppy and young dog are pretty close — close enough that one might reasonably say “puppy is defined as young dog”. (Indeed, checking a couple of dictionaries, it is.) But a young puppy is not redundant: we know it means (in most contexts) a dog that is young even for a puppy. Nor is an old puppy an oxymoron. In isolation, puppy means almost exactly young dog; but it’s picked up different connotations, so in many contexts, replacing puppy with young dog can change the meaning of a phrase significantly. This is why pleonasm is often rather effective: ‘technical’ redundancy can be an illusion.
Substituting synonyms to check whether something makes sense is often helpful nonetheless, as a very rough rule of thumb. But when it doesn’t work, one shouldn’t be too surprised.
The answer to the question is No.You might regard someone with a complete lack of respect! So using regards alone doesn't clearly show how you feel about someone you're corresponding with. Of course in correspondence using "regards" alone doesn't have a negative connotation and is used to show good wishes.
Sometimes pleonastic usage is welcomed. The usages are:
Professional and scholarly use
For getting more information visit Wikipedia
So for emphasizing or making the purpose clear we might use redundancies. For example:
"This was the most unkindest cut of all." —William Shakespeare, Julius Caesar.
No, because I might regard you with disdain, or my worst regards.
Regards doesn't carry with it a very open and public sense of best that you're talking about. Most people probably just understand it as something like "good wishes" or some other non-superlative and bland but positive way to express friendship. So Best regards at the end of a letter, if it got noticed at all, would simply be read as equivalent to Best wishes.
You can also give someone kind regards, or warm regards, so specifying best regards is not redundant. As PLL points out, "regards" by itself does not equate to "best wishes"; I think of it in this usage as "the worth or estimation in which something or someone is held" (Merriam-Webster definition 4a). In effect, you're closing with a little note letting the person know that you have a good opinion of them.
Regards is used to hide the emotional content of your salutation. I once had a manager who told me there is no room for emotion in business, which I do not find to be true.
However, when needing to maintain a professional air surrounding emails and letters, regards is a snappy quick way of saying (more often then not) 'best wishes'; which therefore makes 'best regards' a redundancy.
Thank you for your interest in this question.
Because it has attracted low-quality or spam answers that had to be removed, posting an answer now requires 10 reputation on this site (the association bonus does not count).
Would you like to answer one of these unanswered questions instead?