Leonard Wood

During the Spanish-American War, military officer Leonard Wood, together with his friend Theodore Roosevelt, founded the First Volunteer Cavalry Regiment, popularly known as the Rough Riders. Their success in Cuba propelled Roosevelt toward the White House and led Wood to be appointed the provisional governor of Cuba. Although Wood ruled with an iron fist, effectively disenfranchising the majority of Cuban citizens, he initiated a number of important projects, including a successful campaign to eradicate the deadly yellow fever epidemic. In 1902 he stepped down from his post, having presided over the adoption of a new constitution and the peaceful turnover of authority. He served a similar position in the Philippines before being selected army chief of staff in 1910. John Singer Sargent admired Wood and in 1903 sought out the opportunity to paint his portrait.