Upon earning a medal of honor in 1885 for his service in the campaign against Apache leader Geronimo, Leonard Wood began his military ascent. But it was the War of 1898 that propelled his meteoric rise and that of his friend, Theodore Roosevelt. Together, they founded the First Volunteer Cavalry Regiment, popularly known as the Rough Riders. Their success led to Wood’s appointment as the military governor of Cuba in 1899. 

Although Wood ruled with an iron fist and disenfranchised most Cubans, he initiated important projects, including a successful campaign to eradicate yellow fever. In 1902, Cubans protested in front of Wood’s residence, the governor’s palace, after the United States introduced the Platt Amendment. The amendment stipulated that the end of the U.S. military government was contingent on the ongoing U.S. oversight of Cuban affairs. 

In 1903, John Singer Sargent painted this portrait of Wood in uniform, visually conveying his authority. Later that year, Wood became military governor of Moro Province in the Philippines.