On May 4, 1898, Hawkins was appointed brigadier general in the volunteer army and was in command of the 1st Brigade, 1st Division, VII Corps stationed in Tampa, Florida when the Spanish–American War began. He was transferred to command the 1st Brigade, 1st Division, V Corps and sailed to Cuba. His brigade landed at Daiquirí, was lightly engaged in the fighting at the Battle of Las Guasimas and spearheaded the assault at the Battle of San Juan Hill.
While the main U.S. attack was pinned down under Spanish artillery on San Juan Hill, Hawkins permitted Lieutenant Jules Garesche Ord to begin an attack on the hill and then rushed to the front of the main body of his brigade yelling "Come on! Come on!" and led his troops up the hill where he was severely wounded in the foot near the crest. On July 8, 1898, Hawkins was appointed major general of volunteers and returned to the United States.[1] He retired on October 4, 1898.[1]
Hawkins was the son of Hamilton Smith Hawkins, an Army surgeon from Maryland who was killed during the Mexican–American War.[3][5]
His son, Hamilton S. Hawkins III, was an 1894 West Point graduate who commanded the 1st Cavalry Division from 1934 to 1936.[6][7] His grandson, Hamilton Smith Hawkins IV, was a member of the Military Academy Class of 1926 who received his diploma posthumously after dying in a polo match one month before graduation.[6][8] His son-in-law Robert Lee Howze and two other grandsons were also West Point graduates.
Hawkins and his wife, Annie Gray Hawkins, were buried in Section I of the West Point Cemetery.[9] His son, daughter-in-law and grandson were buried in Section V.[10][11] His daughter, son-in-law and grandson, Hamilton Hawkins Howze, were also buried in Section I.[12][13]
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