Henry B. Drake was born around 1837 in Greenville, Illinois, to Jacob and Elizabeth Drake. His father was a physician who owned $3,000 of real estate by 1850. He grew up and attended school in Bond County, Illinois, and by 1860, he was working as a farmer. He married Miriam E. Harlan on December 29, 1859. Their son Edward was born in the early 1860s, but he apparently died soon afterward. By 1860, they owned $3,100 of real estate and $400 of personal property.
He enlisted in the Union army on August 12, 1862, and he mustered in as a private in Company E of the 130th Illinois Infantry on October 25, 1862. According to his service records, he was 5 feet, 9 inches tall, with light hair and grey eyes. The regiment took part in the Vicksburg campaign, and he died at Vicksburg on May 22, 1863.