Congressman Wheeler promoted his position in the emerging world power when, in 1897, he guided a $50,000 appropriation from the public treasury to the relief of the hungry in civil war ravaged Cuba. Early on he was a fervent proponent of "Cuba Libre". Helping provide attention, preaching American principles of democratic freedom, and expressing loathing for the cruel bullying of the failing Spanish Empire, he would soon provide more than words and money to the cause of Cuban independence. He'd strap on the horse soldier's spurs. He would be 62 years old when he followed the dance music of Mars yet another time in his life.

He was in the President's office on the morning the Washington papers carried the story of the sinking of the "Maine" in Havana harbor. "Fightin' Joe" was the first to volunteer.