Learn Spanish (Latin America): Fue triste que su gran ambición hubiera fracasado. - It was sad that his great ambition had failed.

The phrase Fue triste que expresses a past emotion, which triggers the subjunctive. We need the past perfect subjunctive (hubiera fracasado) because the failure happened before the sadness. If you said Fue triste que fracasara, it would imply the failure and the sadness were happening around the same time.

Could I use hubiese fracasado instead of hubiera fracasado?

Yes, hubiese fracasado is entirely correct and means the exact same thing. Both are valid forms of the imperfect subjunctive of haber. However, the -ra forms like hubiera are much more commonly used in everyday Latin American Spanish.

Why is it gran ambición instead of ambición grande?

When the adjective grande (big or great) is placed directly before any singular noun, it drops the -de and becomes gran. Placing it before the noun, as in gran ambición, gives it a figurative meaning (great or impressive) rather than referring to physical size.

Does fracasar work for any type of failure, like failing a school test?