Medal of Honor-winning military officer and physician (1860-1927) who served as Army Chief of Staff and then Governor-General of Cuba and the Philippines. During the Spanish-American War, he commanded the Rough Riders, with Theodore Roosevelt as his second-in-command. Three items: an ink signature, "Leonard Wood, Maj. Gen. Mil.Gov., Havana, April 18, 1900," on an off-white 3.75 x 2.25 card; an ink signature, "Leonard Wood, Major General USA, March 2, 1917," on an off-white 5 x 3.25 album page affixed to a slightly larger sheet; and a TLS signed "Leonard Wood," one page, 7.25 x 10.5, July 15, 1918, addressed to Mrs. Edward Ascherson, in part: "I often think of the three weeks at the Ritz Hospital and wonder what fortune changed conditions have brought you…I shall always remember with sincere appreciation your many acts of kindness and courtesy…There is no special news here; other than what you see in the Press. I was relieved from command of my Division and returned here just as we were about to sail, greatly to my regret. We still have in America something of politics of the kind which we all regret in time of war." In overall very good to fine condition.