Tuhia he tomokanga mō tēnei wāhanga - I te tīmatanga o ngā pakanga ki a Pāniora, i whakatairangahia ia hei rangatira pirihimana o ngā tūao 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 te Hōngongoi 1898, i muri i te wikitoria a Amerika i te Pakanga o San Juan Hill
I muri i te hinganga o te Rōpū Whakatere o te Rōpū Whakatere o Wheeler, i riro i a Young te mana o te Rōpū Whakatere o Wheeler, a, i whakawhiwhia ki a ia te mana nui o nga kaitautoko i a ia e whakahau ana i taua wehenga ano i Cuba i muri i te Campaign o 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.