Kammala wannan jumla: A ranar 14 ga Yuni, 1898, Paddock da Rundunar Sojoji ta 6 sun bar Florida zuwa Cuba da kuma Yakin Spain-Amurka. A can ne aka san shi da jaruntaka a lokacin yakin basasa.
Yaƙin San Juan Hill a cikin Yaƙin Santiago. Duk da yake a Cuba, Paddock ya kamu da zazzabin cizon sauro, kuma ya kasance a kan rashin lafiya a watan Satumba na shekara ta 1898. Duk da ganewar asali mai kyau, Paddock ya kasance a kan izinin likita sau da yawa ko a karkashin kulawar likita a cikin 1899 yayin da yake zaune a Fort Leavenworth.