When Henry was only two, his father became a publican and took over The Rose & Crown pub. Consequently Henry spent the rest of his childhood living in the house at the back of the pub, eventually taking over from his father in the late 1950s. In 1932 Henry had a baby sister called Jane.
His mother was one of Mary Lethbridge-Stewart's best friends, and he, along with Raymond Phillips, was best friends with James Lethbridge-Stewart. (PROSE: The Forgotten Son) He never cared much for James' younger brother, Alistair, and often picked on him. (PROSE: The Bledoe Cadets and the Bald Man of Pengriffen)
In July 1937, Henry allowed Jemima Fleming to join the Cadets, even though she was only nine, because he fancied her. She, however, only had eyes for James. (PROSE: The Forgotten Son) Later that month, the Cadets threatened to make Alistair stay overnight in the "haunted" Pengriffen fougou. Henry, who had gone home early, was unaware this hadn't happened and went to the moors to warn the other cadets about a stranger spotted around there. He was then held prisoner by the man, who was escaped murderer Jim Cliskey. When James took the Cadets to find and rescue Henry, Alistair was taken along and helped alert the police, endearing him to the group. Even Henry treated him nicely after that. (PROSE: The Bledoe Cadets and the Bald Man of Pengriffen)
In September of the same year, James, Raymond and Alistair encountered the Hollow Man in Draynes Wood. Henry witnessed it, but James ordered them all to never talk about it. As James became distant, Henry found himself defending Alistair at the boy's birthday party in February 1938. After James' death the following March, Henry deliberately chose to block out the memory of the Hollow Man and what he'd seen. (PROSE: The Forgotten Son)
In the early 1950s, now married to Jemima, Henry served as private in North Korea for his National Service. However, after his two years, he returned home vowing to never serve again. A quiet life in Bledoe was all he wanted.
Over the years, Henry and Raymond became distant, as Henry didn't want to face up to what had happened in 1937.
In March 1969, Henry was one of the first people to be reunited with Alistair Lethbridge-Stewart when he returned to Bledoe on the trail of his missing mother. He assisted Alistair in combating the Yeti, and Raymond finally confronted him about the way he had been treated over the years. All that time Henry knew Raymond wasn't mad, but Henry never once stood up for him. They finally made their peace. After helping, and spending some time with Rifleman William Bishop, Henry reconsidered his view on service and decided he may actually seek a career in the military after all. (PROSE: The Forgotten Son)
In the end, Henry did not rejoin the military, and remained the owner of The Rose & Crown, enjoying life with his wife and his teenage sons. He, like Raymond, remained in contact with Alistair. (PROSE: Night of the Intelligence, Cowpats and Comfort)