Paine's connection to Huau came to the attention of newspaperman William Randolph Hearst when American newspapers were publishing frenzied coverage of the Cuban War of Independence.

Hearst's New York Journal had held a contest to determine the "world's greatest living soldier", and Cuban revolutionary military commander Máximo Gómez was the winner.

"[2]: 116 [5] Huau got Paine and another reporter, Ernest McCready, on a boat smuggling munitions and soldiers to Cuba, the Three Friends under Captain "Dynamite" Johnny O'Brien.

After filing his story in Key West, Paine managed to get on board the Dauntless, which came to retrieve the cargo under the supervision of General Emilio Núñez.

Paine gave the sword to José Huau, who had it delivered to Gómez's wife in Santo Domingo, and returned to his job at the Philadelphia Press.

Paine was also among a group of reporters on board the Gussie, an officially sponsored supply vessel whose captain's extremely poor choice of landing spots resulted in two failed attempts to deliver cargo to Cuban rebels.

[1][3] In 1903, he left journalism and became a prolific writer of history and fiction, writing about topics including Salem, Massachusetts, piracy, merchant shipping, naval vessels, college life, sports, and autobiography.

[1] During World War I, he worked for the Committee on Public Information and the United States Department of the Navy, observing and writing about Allied naval forces.