Dhameystir weedha soo socota: Wood wuxuu ahaa dhakhtarka gaarka ah ee Madaxweyne Grover Cleveland iyo William McKinley ilaa 1898. Intii uu joogay Aqalka Cad, Wood wuxuu xiriir saaxiibtinimo la yeeshay Theodore Roosevelt, ka dibna Wasiir Ku-xigeenka Ciidanka Badda. Markii uu billowday dagaalkii Spain iyo Mareykanka, Wood iyo Roosevelt waxay abaabuleen Guutada 1aad ee Gaashaanleyaasha Iskaa wax u qabso ah, oo caan ku ah Rough Riders. Wood wuxuu si guul leh u amray guutada intii lagu jiray 24-kii Juun, 1898 Dagaalkii Las Guasimas. Markii taliyaha guutada, Samuel B. M. Young, uu xanuunsaday, Wood wuxuu helay dallacaad goobta ah oo loo magacaabay brigadier general of volunteers. Wuxuu qabtay amarkii Guutada 2aad, Qaybta Fardooleyda, Ciidanka Shanaad ee Ciidanka (oo ay ku jiraan Rough Riders) wuxuuna hoggaamiyay guutada guushii caanka ahayd ee July 1, 1898 ee Kettle Hill iyo
Buuraha sare ee San Juan.