YOU SAID:
He came to me with money in his hand, I didn’t ask him
INTO JAPANESE
彼は手に金を持って私のところに来た、私は彼に尋ねなかった
BACK INTO ENGLISH
He came to me with money in hand, I did not ask him
INTO JAPANESE
彼は手元にお金で私に来た、私は彼に尋ねなかった
BACK INTO ENGLISH
He came to me with money on hand, I did not ask him
INTO JAPANESE
彼は手元にお金で私に来た、私は彼に尋ねなかった
BACK INTO ENGLISH
He came to me with money on hand, I did not ask him
That didn't even make that much sense in English.