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Raj has breakfast almost always before 7:45 AM. On rare occasions, he has after 7:45 AM, but never after 8:00 AM. So If he says "I always have my breakfast latest by 8:00 AM" to convey this fact, is Raj's usage correct?

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Depends...what variety of English does Raj speak? In General American English it doesn't sound right, he would say '...breakfast at the latest by...' – Mitch Apr 16 '12 at 12:48
I have heard this usage in India. Probably, the "at the" is ignored. – MediumOne Apr 16 '12 at 13:14
We have a tag "Indian English" ... should that be added here? It would be "incorrect" of us to say that Raj is incorrect, if Raj is in India... – GEdgar Apr 16 '12 at 13:19
This is incorrect in American English, but I know I've heard it. I was going to say it sounded British, but Barrie's answer seems to say it's not used in the U.K. From the comments, it sounds like this is Indian English. I'm guessing that it (like prepone) is widely used there, and so should be presumed to be correct for Indian English. – Peter Shor Apr 16 '12 at 14:04
This is not correct in educated circles in India. Probably it is OK for an Indian family learning to talk in English amongst themselves! – Bravo Apr 16 '12 at 14:30

By eight o'clock at the latest would be the usual way to put it.

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In BrE, would '...at latest...' be an acceptable alternative? – Mitch Apr 16 '12 at 13:20
@Mitch: It might be found in some regional dialects, but not in British Standard English. – Barrie England Apr 16 '12 at 14:43

The question is about the use of the word latest in the particular sense of not later than.

According to the answers here, YES, latest in this sense is used in the US, in the UK, in India, and possibly elsewhere.

All other issues are out of the scope of the OP's question.

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