Whakaotihia te rerenga e whai ake nei: I te timatanga o nga pakanga ki Spain, i whakatairangahia ia ki te rangatira rangatira o nga kaitautoko i te marama o Mei 1898. I Cuba i te wa o te pakanga, i whakahau ia i tetahi o nga roopu hoia hoia e rua i uru ki te Ropu Rererangi i raro i a Major General Joseph Wheeler. Kei roto i te parirau a Young nga Rough Riders a Theodore Roosevelt, te 1st US Volunteer Cavalry Regiment. I roto i te Hōngongoi 1898, i muri i te wikitoria American o te
I te Pakanga o San Juan Hill, i riro i a Young te mana o te Wheeler's Cavalry Division, a, i whakawhiwhia ki a ia hei rangatira nui mo nga kaitautoko i a ia e whakahau ana i taua wehenga ano i Cuba i muri i te Campaign Santiago o te Pakanga Paniora-Amerika. I taua tau ano, ka noho a Young hei Kaihauturu Pakeke o te Missouri Commandery of the Military Order of Foreign Wars.