Henry was born in Kiana to Isaac and Jennie Sheldon Jackson on November 23, 1924. He and his siblings grew up in the "old village" which was near the Squirrel River outlet, just below the end of the present day Kiana airstrip. Henry's brothers and sisters include Ray, Clifton, Clarence, Fred, Kitty and Annie. Florence and Lulu died in infancy. In younger days, Henry spent time below Noorvik hunting muskrat in the spring. He spent the rest of the year fishing up the Squirrel River. Occasionally he spent time at Coal Mine. Eventually, the family settled at present-day Kiana. Henry and his wife Lucy were schoolmates and married in 1946. Lucy's maiden name was also Jackson and she is one of Percy Jackson, Sr.'s sisters. Henry and Lucy had eleven children. They are currently raising six of their grandchildren, all of whom have grown up in Kiana. Henry worked in mining operations at Candle and then moved to Nome where he helped construct the Maynard McDougal Memorial Hospital and, later, worked in mining activities. Henry has paid his dues as a member of the Operators Union 302 for thirty years. He worked as an Operator for three months in Noatak and three months in Kivalina during the construction of their airports. He also worked on the construction of the Trans-Alaska Pipeline from 1969 to 1982. Henry was a member and one-time president of the Kiana Dog Mushers Association when it was active in the 1950's and 1960's. Henry served on the Kiana City Council for many years in the past.