Kammala wannan jumla: Wood ya kasance likitan likita ga Shugabannin Grover Cleveland da William McKinley har zuwa 1898. A lokacin da yake aiki a fadar White House, Wood ya kulla abota da Theodore Roosevelt, sannan Mataimakin Sakataren Sojojin Ruwa. A lokacin da aka fara yakin basasar Spain da Amurka, Wood da Roosevelt sun shirya rundunar sojan doki na 1st Volunteer, wanda aka fi sani da Rough Riders. Wood ya yi nasarar umurni da rundunar a ranar 24 ga Yuni, 1898 a yakin Las Guasimas. Lokacin da kwamandan brigade, Samuel B. M. Young, ya yi rashin lafiya, Wood ya sami ci gaba a fagen zuwa brigadier janar na masu sa kai. Ya dauki umurnin 2nd Brigade, Cavalry Division, Fifth Army Corps (wanda ya hada da Rough Riders) kuma ya jagoranci brigade zuwa sanannen Yuli 1, 1898 nasara a Kettle Hill da
San Juan Heights. Wannan shi ne San Juan.