YOU SAID:

What he had had had had had had had had gone, and it had had had had made him sad.

INTO JAPANESE

彼が持っていたものはなくなっていた、そしてそれは彼を悲しませた。

BACK INTO ENGLISH

What he had was gone, and it made him sad.

INTO JAPANESE

彼が持っていたものはなくなり、それは彼を悲しませた。

BACK INTO ENGLISH

What he had was gone, which made him sad.

INTO JAPANESE

彼が持っていたものがなくなったので、彼は悲しくなりました。

BACK INTO ENGLISH

He was sad because he had nothing.

INTO JAPANESE

彼には何もなかったので彼は悲しかった。

BACK INTO ENGLISH

He was sad because he had nothing.