Henry was born about 1839 and Richard followed in about 1842. According to census records the Crupper men all worked on steamboats. Their father John was a steamboat mate with an estimated real estate value of $800 in the 1850 Census. By the 1860 Census John is missing and I presume dead. His wife Winifred is now working as a seamstress. Her three sons are all employed on steamboats. William is an engineer, Henry a mate and Richard is a cabin boy. A few doors down is Franklin Bryan, a steamboat captain. Perhaps he employed the boys after the death of their father.
Henry doesn't appear to have particpated in the Civil War. I've not found any records for him to date. The story is much different for his brother Richard.
During the Civil War Richard enlisted with the Union Army and served in the 15th Kentucky Infantry. Military records describe him as 5' 9 1/2" tall. Complexion light, eyes blue, hair light. Occupation, boatman. In March 1863 and at the young age of 21 he was promoted from Second Lieutenant to Captain due to a vacancy. He was mustered out on January 15, 1864. After the war he made his way to Memphis where he worked as a sergeant on the Metropolitan Police force. He appears in the Memphis City Directory for 1867 with his brother Henry. They are living at 25 Causey.
Then the following notice appears in the Memphis Daily Appeal no Nov 5, 1867:
Death of Sergeant Crupper
|Fallen Police Memorial|
Richard was buried at Elmwood Cemetery and his name appears on the Fallen Police Memorial dedicated "To Our Comrades". It seems likely that he died of yellow fever as Elmwood records indicate that cause of death for many people at that time was yellow fever. In 1867 there were 2500 cases with 550 reported deaths in Memphis.
His brother Henry remains in Memphis. The last time we see him is in the 1878 City Directory and his occupation is listed as engineer. The 1878 Yellow Fever Epidemic in Memphis was devastating. There were 17000 cases with over 5000 deaths reported. The epidemic continued into 1879 with the number of cases being reported as 2000 with 600 deaths. Henry Crupper was among that 600. He succumbed to yellow fever on October 23, 1879 and is buried near his brother. I believe he lies in an unmarked grave.