YOU SAID:
Jackson is not not smart and is indeed a very smart and helpful person.
INTO JAPANESE
ジャクソンは賢くないわけではなく、確かにとても賢くて親切な人です。
BACK INTO ENGLISH
It's not that Jackson isn't smart, he's certainly a very smart and kind person.
INTO JAPANESE
ジャクソンが賢くないわけではなく、確かにとても賢くて優しい人です。
BACK INTO ENGLISH
It's not that Jackson isn't smart, he's certainly a very smart and kind person.
That didn't even make that much sense in English.