Rubuta ci gaba ga wannan sakin layi - A farkon tashin hankali da Spain, an ba shi mukamin 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 a yakin San Juan Hill
, Young ya karbi umurnin Rundunar Sojojin Sojojin Wheeler kuma ya zama babban janar na masu sa kai yayin da yake umurni da wannan rukuni a Cuba bayan Kamfen na Santiago na Spanish-American War. A wannan shekarar, Young ya zama Abokin Tsohon Sojoji na Missouri Commandery na Sojojin Sojojin Kasashen Waje.