Marka uu bilaabmo dagaalkii Isbaanishka, waxaa loo dalacsiiyay janaraal guuto iskaa wax u qabso ah bishii May 1898. Intii lagu jiray dagaalka Cuba, wuxuu amar ku bixiyay mid ka mid ah laba guuto oo fardooley ah oo qayb ka ahaa Qaybta Fardooleyda ee Major General Joseph Wheeler. Ciidanka Young waxaa ka mid ahaa Theodore Roosevelt's Rough Riders, 1aad US Volunteer Cavalry Regiment. Bishii Luulyo 1898, kadib guushii Mareykanka ee Dagaalkii San Juan Hill
, Young wuxuu la wareegay amarka qeybta Wheeler's Cavalry Division waxaana loo sameeyay sarkaal sare oo mutadawiciin ah halka uu ku amray isla qeybtaas Cuba kadib ololihii Santiago ee dagaalkii Isbaanishka iyo Mareykanka. Isla sanadkaas, Young wuxuu noqday Saaxiibka Halyeeyga ah ee Missouri Commandery ee Amarka Milatari ee Dagaallada Dibadda.