Among the people I know my father quit working latest.

[navi tasan]

1) Among the people I know my father quit working latest.
2) Among the people I know my father quit working latest in life.

3) Among the people I know my father kept working latest in life.
4) Among the people I know my father kept working latest in life.

5) Among the people I know my father had the highest age when he quit working.
6) Among the people I know my father was the oldest when he quit working.

I think the idea itself is simple but it seems hard to express, or maybe I have a block or....
He didn't necessarily work longer than all the others, but nobody quit at an age older than the age he had when he quit.
I think '5' and '6' are grammatical, but they mean something else, which is weird.

 

[Barque]

My father retired at a later age than anyone else I know.

All your sentences are grammatical but most of them aren't what would normally be said. I think your sentences 1 and 6 are better than the others.

 

[emsr2d2]

"Among the people I know" is fairly unnatural regardless of what comes after it. I'd expect "Of everyone I know, ...". Note that both your original version and mine require a comma after "know".

 

[navi tasan]

Thank you both very much,

Barque's sentence is a lot more elegant than mine.


7) Of everyone I know my father quit working latest.

(I modified my '1' according to emsr2d2's recommendation)

Could '7' even have the meaning I have in mind? Or does it mean that everyone I know quit working earlier than my father, but not necessarily at a younger age?

 

[Barque]

Or does it mean that everyone I know quit working earlier than my father, but not necessarily at a younger age?

Technically, yes, that's what it means. But I think people would understand what you meant--that no one else, on their last working day, was as old as your father was on his.

 

[Tarheel]

Barque's use of "retire" is much more natural. (Didn't @emsr2d2 point that out?)

 

[White Hat]

Would it be wrong to use 'the' before 'latest' in this case?

 

[Tarheel]

No, it would not be wrong.

 

[White Hat]

No, it would not be wrong.

Would doing so change the meaning?

 

[Tarheel]

No, I don't think so.