Possible Results:

habría enorgullecido

Conditional perfectyoconjugation ofenorgullecer.

habría enorgullecido

Conditional perfectél/ella/ustedconjugation ofenorgullecer.

enorgullecer

Él se habría enorgullecido de mí.	What? I could have made him so proud.
Tu abuelo se habría enorgullecido de ti.	You would have made your grandfather proud.

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