 On February 12, 1894 Smith married Marie Antionette Wright, described as "a Louisville girl" and soon after went to Cuba, reporting for the "New York Herald" on the guerilla operations of Antonio Maceo Grajales.He later returned to Cuba, at the outbreak of the Spanish–American War (1898), reporting for the "New York Journal".According to Brown,

In October 1897 Smith, along with fellow sports reporter Danny Smith, was sent by the "New York Herald" to Carson City, Nevada, where he covered the boxing match between James J. Corbett and English boxer Bob Fitzsimmons.