Rubuta ci gaba don wannan sakin layi - A cikin 1445, Henry ya shiga cikin Yaƙin Olmedo na Farko
, yana taimaka wa ɗan'uwansa, Sarkin Navarre, a kan ɗan'uwansu, Sarkin Castile. A cewar wata ka'ida, Sarkin Navarre ya shirya ya ci kudancin yankin Masarautar Castile kuma ya ayyana Henry a matsayin sarkinsa. Duk da haka, Henry ya ji rauni kuma ya mutu daga kamuwa da cuta 'yan makonni bayan haka.