— Autograph February 2009

TLS on Outlook stationery by Theodore Roosevelt, who was awarded a controversial Medal of Honor in 2001 for his actions at San Juan Hill. When I was a teen these sold for $15-20, I more recently paid $350.

In American history, certain battles of its wars hold an iconic status: Lexington and Concord, the Battle of Bunker Hill, the Alamo, Gettysburg, Belleau Wood, Pearl Harbor, Guadalcanal, Iwo Jima and the Battle of the Bulge, to name a few. When people think of the Spanish-American War of 1898, they think of the Battle of San Juan Hill. And when Americans think of this battle, they think of Teddy Roosevelt charging up the hill, followed by his Rough Riders, an all-American mix of cowboys, Ivy Leaguers, Pawnee Scouts, polo players and New York  City policemen.

It was “A Splendid Little War,” created by the jingoism of the yellow press techniques of William Randolph Hearst and others, whose propaganda caused the public and the politicians to demand that a hesitant President McKinley go to war to kick the cruel Spanish out of Cuba, and to “Remember the Maine.” It was clearly an optional war and though we passed a law that we would not annex Cuba, we ended up with the Spanish colonies of the Philippines, Puerto Rico and Guam.

Leading Figures

The Spanish-American War is barely remembered today and mostly what we know of it is due to one man, Theodore Roosevelt. Roosevelt was one of our most colorful and important of presidents, and it was his charge up San Juan Hill that eventually gave him the presidency. His history is well known and in recent years has been dissected by a number of historians. Roosevelt was many things, but one thing he did all his life was push himself to the end of his limits and expected the same from others. As assistant secretary of the Navy in the McKinley administration, Roosevelt’s machinations helped bring on the war. More than anything he wanted to serve in it and prove himself a “man.” When Roosevelt proposed to Secretary of War Russell Alger the concept of the Rough Riders, otherwise known as the 1st U.S. Volunteer Cavalry Regiment, Alger agreed, offering him a colonelcy and command. But, Roosevelt suggested Col. Leonard Wood to help him lead the volunteers.

Col. Leonard Wood was the actual leader of the Rough Riders, an Indian War Medal of Honor recipient and later a presidential hopeful.

Lt. Col. Wood was an Army physician, and Presidents Cleveland’s and McKinley’s personal physician, who had gained fame and a Medal of Honor for his actions in fighting Geronimo in 1886. While in Cuba he replaced the ill Gen. Samuel B. M. Young as the commander of the Second Cavalry Brigade, which included the Rough Riders. Wood is an important autograph of a San Juan Hill collection because, despite the fact that the calvary will be forever known as “Roosevelt’s Rough Riders,” he was technically the commander. He went on to become

Gen. Nelson Miles, Medal of Honor recipient, Indian fighter and overall leader of the forces during the Spanish-American War.

governor of Cuba, chief of Army staff and was a major candidate for the 1920 Republican presidential nomination. His signature can cost around $100. Wood may have officially been in charge, but there was never any doubt that Roosevelt was the real head of the Rough Riders.

The overall war was commanded by Gen. Nelson Miles, a Civil War Medal of Honor recipient, wounded four times and later known as the great Indian fighter. The command in Cuba fell to Gen. William Shafter, another Civil War Medal of Honor recipient and Indian fighter. He was in his 60s, weighed well over 300 pounds and suffered badly in the tropical heat. Because of his gout, he had to be carried on a door, but he used good sense in capturing Santiago, the main objective, through the use of the Navy and through peace negotiations. Roosevelt wasn’t pleased with this because it denied him the chance to fight another battle after San Juan Hill. President McKinley’s choice to lead the cavalry, including the Rough Riders, was the aging and diminutive Confederate Cavalry Gen. “Fighting Joe” Wheeler, who McKinley believed would help bring the nation together.

The confused Wheeler mistakenly called the Spanish “Yankees” and, despite his age of 61, road to the gunfire at San Juan Hill. As a Confederate hero of the Civil War, Wheeler’s autograph is highly desirable, and since he served in Congress between wars, it’s also fairly plentiful with a signature selling for $100-$150. Gen. Miles and Shafter both also sell in the same range.

Not So Splendid A War

Gen. Lytle Brown graduated from the Military Academy at West Point the same year as the San Juan Hill battle. He was a top engineer in WWI, president of the U.S. Army War College and head of the Panama Canal Zone.

The majority of the regular Army who fought in the war, plus volunteers, made up a force of massive proportions—so large that there were not enough bullets in the country to meet their needs. Getting the troops to Cuba and supplying them was poorly planned. The war was brief, lasting only from April to August (with the final peace treaty being signed in December), but it was bloody. Once in Cuba, the Americans found the roads almost impassible, food largely unavailable and the soldiers out-gunned by smokeless rifles that picked off the troops almost from the time they reached land.

Confederate Cavalry Gen. “Fighting Joe” Wheeler led the cavalry in Cuba.

Several bloody skirmishes were fought before reaching the two hills that overlooked Santiago: Kettle Hill, named for a huge kettle found at the top, and San Juan Hill beside it. The troops waited below, being picked off for hours before the final order was given to charge. There is still controversy today as to who made the final call to charge, but once made, the Americans faced a small but well entrenched group of Spaniards at the top.

The charge is where history and fact part ways. We think of Roosevelt, alone, leading the Rough Riders to victory. In fact, he was a part of one of many groups who made the charge. They were dismounted cavalry

Gen. John “Black Jack” Pershing led African-American troops in the attack on San Juan Hill. One of the more expensive San Juan Hill autographs, Pershing headed the American forces in WWI.

and infantry, primarily led by regulars including a large number of African-Americans. Five African-Americans were awarded the Medal of Honor for their actions in the battle.

Roosevelt showed great bravery in what he considered the greatest day of his life, and within days was shamelessly lobbying for a Medal of Honor. His duplicity in the war and his back-biting against his superiors had left a sour taste in the mouths of the War Department, who felt that, while brave, he was no braver than others. He went to his death regretting that he had not received the medal, but in January 2001, despite opposition, and the fact that some believe he really didn’t deserve it, he was awarded the Medal of Honor posthumously by President Bill Clinton.

Other Generals

Gen. T. A. Baldwin lost 20 percent of his men and 50 percent of his officers in the charge up San Juan Hill, and received personal commendations from President McKinley and Gen. Wheeler.

Besides the leaders, a number of generals who gained fame in WW I were part of the attack on San Juan Hill. Among these are a few from my collection, such as Gen. John “Black Jack” Pershing, who won the sobriquet “Black Jack” because he commanded black troops and was an officer in the charge; Malvern Hill Barnum, the son of Civil War Gen. Henry Barnum, who was cited for gallantry as part of the 10th Cavalry; Gen. Charles Crawford, who led the 3rd Infantry Division in WWI; Gen. Frank McCoy who was wounded; and others include Gen. Lytle Brown, Gen. T. A. Baldwin and Gen. Samuel S. B. Young.

Many important officers played a role in the battle at San Juan Hill, and it’s an adventure to find them. Many who were also in WWI can be found for as little as $25 for a letter.