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    #1

    the man to serve his sentence

    Can one use:

    1-That officer standing at the bar arrested the first man to serve his sentence in the new prison.
    If the 'man' hasn't served his sentence yet, but is to serve his sentence?

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    #2

    Re: the man to serve his sentence

    Here's the meaning I get from that sentence:

    officer/ arrested /first man

    (who would) serve his sentence in the new prison.

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    #3

    Re: the man to serve his sentence

    Thanks Susiedqq,

    Can't it also mean:

    That officer standing at the bar arrested the first man who served his sentence in the new prison.

    I think the 'serving' could happen either in the future or in the past, depending on the context.

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    #4

    Re: the man to serve his sentence

    Yes, he arrested the first person who had ever served his sentence in the new prison.

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