Kammala wannan jumla: A farkon tashin hankali da Spain, an daukaka shi zuwa brigadier janar na masu sa kai a watan Mayu 1898. A Cuba a lokacin yakin, ya umurci daya daga cikin brigades guda biyu da suka kasance wani ɓangare na Rundunar Sojoji a karkashin Major General Joseph Wheeler. Rundunar Young ta hada da Theodore Roosevelt's Rough Riders, na farko na Rundunar Sojan Amurka. A watan Yulin 1898, bayan nasarar Amurka na
Yaƙin San Juan Hill, Young ya ɗauki umurnin Rundunar Sojojin Wheeler kuma ya zama babban janar na masu sa kai yayin da ya umurci wannan rukunin a Cuba bayan Kamfen na Santiago na Yakin Spain-Amurka. A wannan shekarar, Young ya zama Abokin Tsohon Sojoji na Missouri Commandery na Sojojin Sojojin Kasashen Waje.