Herbert Howland Sargent was an American colonel, military professor and author during the Spanish-American War and the Filipino-American War. He was known for his effective leadership and training of the 5th Volunteer Infantry Regiment, being notable for its efficiency and well-disciplined soldiers. He was also a historian of the Napoleonic Wars, writing several acclaimed works about its events. Early career Herbert was born on September 29, 1858, as the son of Jacob True and Maria Lucretia (née Bayley) Sargent at Carlinville, Illinois. Sargent enrolled in the United States Military Academy from July 1, 1879, to June 13, 1883, when he graduated as a Second Lieutenant on June 13, 1883, within the 2nd Cavalry Regiment. He was then sent on Frontier service at Fort Assinniboine, Minnesota from September 28, 1883, until June 3, 1884, when he was briefly transferred to Fort Klamath, Oregon on August 16, 1886. Around the same time, he married Alice C. Applegate on August 11, 1886. Sargent then served as a professor of Military Science and Tactics at the University of Illinois from August 29, 1886, to August 31, 1887. He then returned to serve in the Frontier, serving at Fort Bidwell, California on October 20, 1888, and then to Fort Walla Walla in July 1890 and promoted to First Lieutenant on June 19, 1890. He was then sent to Arizona in November 1894 and Colorado in June 1895 where he was appointed Regimental Quartermaster on June 13, 1895. Spanish-American War After being sent to New Mexico in April 1898, the Spanish-American War broke out and despite initially declining promotion to Major of Volunteers and as an Adjutant General, Sargent was then made Colonel of the newly formed 5th Volunteer Infantry Regiment on May 20, 1898, and raised the regiment at Columbus, Mississippi. The regiment was then ordered for Santiago de Cuba on August 6, 1898, and so the regiment went to Savannah, Georgia on August 8 and arrived four days later. Upon arriving at Cuba, the 5th Volunteer Infantry remained in camp for eight months at the outskirts of the city as the regiment played a role in guarding government property during the city's siege. In March 1899, the regiment took command of the District of Guantanamo and Sargent was acting military governor until May 2 when the Regiment returned to Camp Meade and was mustered out on May 31, 1899. Around this time, Sargent was