YOU SAID:

im glad hes dead, he should have died a long time ago

INTO JAPANESE

彼は死んでうれしい、彼はずっと前に死んでいたはずだ

BACK INTO ENGLISH

I'm glad he's dead, he should have died a long time ago.

INTO JAPANESE

彼が死んでくれ、ずっと前に死んでいたはずだ。

BACK INTO ENGLISH

He died, and he should have died a long time ago.

INTO JAPANESE

彼は死んだ、と彼はずっと前に死んでいたはずです。

BACK INTO ENGLISH

He died, and he should have died long ago.

INTO JAPANESE

彼は死んだ、そして彼はずっと前に死んだはずだ。

BACK INTO ENGLISH

He's dead, and he should have died a long time ago.

INTO JAPANESE

彼は死んだし、ずっと前に死んでいたはずだ。

BACK INTO ENGLISH

He's dead, and he should have died a long time ago.