YOU SAID:
the way that that guy was crying was very sad
INTO JAPANESE
あの男が泣いていたのは、とても悲しかった
BACK INTO ENGLISH
It was very sad that he was crying.
INTO JAPANESE
彼が泣いていたのはとても悲しかった。
BACK INTO ENGLISH
It was very sad that he was crying.
That didn't even make that much sense in English.