Our Arklahoma Heritage: The true story of an Arkansas journalist who spent time in a Cuban prison during the Spanish-American War

The the quiet settlement of Aurora consisted of a few farms and a crossroads store in the late 19th century. Among its residents was Colonel D. W. Milton, a former Confederate lieutenant, who lived there with his family.

His son Owen Milton, was born in Aurora around 1874. Of medium height with pleasant features, Owen graduated from an Arkansas college and spent three years teaching school in the state.

In the spring of 1896, the 22-year-old teacher left the Ozarks for Florida. He signed on with the schooner Competitor as a newspaper correspondent. The vessel carried arms and supplies for Cuban rebels fighting Spanish colonial rule. The uprising on the island had begun the previous year, and expeditions like this one regularly departed from American ports with volunteers and material aid.

Sympathy for the Cuban cause ran strong in the South, where many saw parallels to their own past struggles.

The Competitor sailed in April. Spanish gunboats patrolled the waters off Cuba. On April 25 they seized the schooner and took five men into custody: two Cubans named Bedia and Maza, the Englishman James Kildea, the commander Alfredo Laborde (born in New Orleans), and Owen Milton.

They were transported to Havana. A military court-martial quickly convicted all five of piracy and treason, sentencing them to death by firing squad. Word of the condemnation spread through American newspapers by mid-May. In Jacksonville, Florida, Confederate veterans organized protests on behalf of Owen, the son of one of their own officers.

Telegrams and petitions reached Washington. The United States government pressed Spain to grant the prisoners a civil trial instead of summary military justice. Britain made similar demands for Kildea. Under diplomatic pressure from Madrid, Captain-General Valeriano Weyler stayed the executions.

The men remained in Havana prisons for months while diplomatic cables crossed the Atlantic and American opinion sharpened. Back in Aurora, the Milton family and neighbors followed the developments through the papers.

Owen had carried no weapons; his role centered on reporting. Resolution came on January 23, 1897, the saint's day of the Spanish king. Spain released the American political prisoners on the condition that they provide no further assistance to the insurgents. Owen and the others walked free.

The affair quieted as tensions between the United States and Spain moved toward open war in 1898.

Owen returned to Arkansas. No records show that he resumed teaching or took any public role tied to the voyage. Details of his later years, any marriage or children, and his eventual death have left no clear trace in available sources.

Madison County and surrounding Ozark counties have many small family and community cemeteries. He most likely rests in one near Aurora or in a larger nearby town such as Huntsville or Eureka Springs, possibly in an unmarked or simply marked grave in a family plot with his fathe.r

His father, Col. D. W. Milton, continued to live in the area for some time afterward. Owen’s name appears in connection with the Competitor only during the weeks of his capture and release. He stepped back into private life in the hills where he had grown up.

The Competitor incident marked one of the final filibuster efforts before the Spanish-American War shifted events in Cuba. In Madison County, the episode remained a local memory of how a young man from Aurora had briefly crossed into larger history and returned.

The roads through the Boston Mountains still follow the same ridges, and the story of Owen Milton survives as a footnote to one Arkansas teacher’s encounter with revolution and diplomacy at the end of the nineteenth century.