Soon after the American battleship Maine was destroyed in an explosion while anchored in Havana Harbor, Cuba, on 15 February 1898, thirty-nine-year-old Assistant Secretary of the Navy Theodore Roosevelt left his government post to recruit a volunteer cavalry regiment to be raised in the Western territories for active service in Cuba during the Spanish-American War.

Roosevelt's regiment was officially the First United States Volunteer Cavalry Regiment, but quickly became known as the Rough Riders. View online presentation of Roosevelt in his Rough Rider uniform. Roosevelt fought against the use of the term, but as he noted, "to no purpose," and when the name began to appear in official communications, "we adopted the term ourselves." The Rough Riders became one of the most highly publicized regiments in United States military history not just because of their battlefield exploits, but also because of their colorful (acting) commander at San Juan Hill and exotic origins. There was a full contingent of cowboys, Indians, ranchers, and Western lawmen in the regiment as the name implied; but also, according to their muster roll: polo players, students, songwriters--and sixteen lawyers.

Roosevelt was wise enough to know that he was not competent to lead a regiment into battle--at least not without the month's training that he thought he needed--so he recruited Captain Leonard Wood, one of the most interesting and unusual officers in the United States Army to lead the regiment with the rank of colonel. Wood was a Harvard-trained surgeon who had won the Medal of Honor for his service as a regular soldier during the Apache wars. Roosevelt, as lieutenant-colonel, served as the second in command.

Roosevelt and Wood raised and equipped the Rough Riders so quickly that most of the regiment was able to join the regular cavalry division sent (albeit without horses) in the attack on Santiago, Cuba, in June 1898. Due to Roosevelt's political connections and Wood's military expertise, the Rough Riders were equipped like the regulars with modern, magazine rifles, while, as Roosevelt notes in his letter, the "other volunteers [were] at a hideous disadvantage owing to their not having smokeless powder" for their obsolete weapons.

On 1 July 1898, General William Shafter, the commander of the American forces besieging Santiago (and--according to Roosevelt--the worst commander since Roman times), launched an attack along the entire line of Spanish defenses east of Santiago. The role of the Rough Riders, who held the position at the extreme right end of the main American attack on the San Juan Heights, was not to assault San Juan Hill directly, but rather to attack a subsidiary Spanish position, Kettle Hill. The impetus of their attack and the enthusiasm of Roosevelt, however, carried them forward to the northern end of San Juan Hill, a strategic position overlooking Santiago--and everlasting fame.

In the immediate aftermath of the battle, however, the morale of the American forces surrounding Santiago began to slip. There was no sign of an early end to the siege and the regiments that had made the attack on the San Juan Heights had suffered fifteen hundred casualties, approximately ten percent of "unwieldy" General William Shafter's entire army. Roosevelt tried to buck up his men, but in this letter to Henry Cabot Lodge, as author Evan Thomas has noted, "he betrays his anxiety and uncharacteristic despair."

Few documents show so vividly the contingency of history: Roosevelt believed the situation was so dire that he was prepared to go outside the army chain of command to send a message directly to the president. In fact, the result of the battle on 1 July was almost exactly opposite what Roosevelt expected. Within two weeks the Spanish would lose their naval squadron at Santiago and surrender the city. Between his own well-advertised pride in his conduct, and the large number of American newspaper correspondents present to record his notable and very visible role, Roosevelt became an instant celebrity. His post-battle jitters remained unknown or were soon forgotten. Within a few months of writing this letter, he would be elected governor of New York; in 1900 he was chosen as the Republican candidate for vice-president; a year later, when William McKinley was assassinated, Roosevelt became president.

Henry Cabot Lodge and Theodore Roosevelt

In 1898, Massachusetts Senator Henry Cabot Lodge (1850-1924), the recipient of the letter, was Theodore Roosevelt's best friend and chief political adviser. Roosevelt (1858-1919) later recollected that they had first met at the Porcellian Club at Harvard University, where they were nine years apart in their respective college classes. Republican Party politics brought them together in 1884, when the two young firebrands had to decide whether they would support the tainted presidential candidacy of James G. Blaine, who was anathema to their fellow political reformers. They held their noses and supported Blaine. The death of Roosevelt's first wife, Alice Hathaway Lee, the same year caused Roosevelt to leave politics briefly for a career as a rancher in the Dakotas. He soon returned East to marry Edith Kermit Carow, a childhood friend, with whom he raised six children. Roosevelt served on the United States Civil Service Commission and as president of the New York City Police Board. In the meantime, after two unsuccessful attempts, Henry Cabot Lodge had been elected first to the United States Congress from Massachusetts in 1886, and then to the Senate in 1893, a position that he held for the rest of his life.

With the election of Republican William McKinley to the presidency in 1896, Lodge worked behind the scenes to secure a position for his protégé Roosevelt in the federal government. In 1897, Roosevelt became assistant secretary of the navy under John D. Long, a former governor of Massachusetts. Both before and after the sinking of the Maine, Lodge and Roosevelt agitated relentlessly for intervention in Cuba and the expansion of U.S. interests overseas. Roosevelt and Lodge remained friends for the rest of their lives, although their relative positions in government were reversed when Roosevelt became president in 1901, and their friendship would be severely tried in 1912 when Roosevelt bolted from the GOP to run for president as the Progressive "Bull Moose" candidate. The letter to Henry Cabot Lodge displayed here is located in one of the Historical Society's most remarkable collections, the personal correspondence of the two men from 1884 until Roosevelt's death in 1919.