YOU SAID:

if they're holding the guy in older prison

INTO JAPANESE

もし彼らが古い刑務所に男を抱えているなら

BACK INTO ENGLISH

If they have a man in an old prison

INTO JAPANESE

彼らに古い刑務所に男がいたら

BACK INTO ENGLISH

If they had a man in an old prison

INTO JAPANESE

彼らに古い刑務所に男がいたら

BACK INTO ENGLISH

If they had a man in an old prison