失敗して

fail and

→ 失敗
phrase Rare #32,547
fail and The て-form connects this action to what follows; depending on context, it can also express that something happened after or because of the failure.
JA: 試験に失敗して、もう一度勉強し直した。
EN: I failed the exam and studied again.

彼は二度入試に失敗して大学に入学した。

He failed the entrance exam twice before getting into college.

脱獄に失敗して死んだ

He died after failing to escape from prison.

— Carandiru (2003)

失敗してあれほど悲しそうな顔をする奴が、いるかな?

I wonder if there’s anyone who looks that sad after failing.

仕事に失敗して私は文無しになった。

I failed at work and ended up penniless.