Henry Dye Boggess was born the seventh of 13 children to Jeremiah and Rebecca Boggess on September 30, 1870, in Collin County. His father served in the Confederate Army throughout the Civil War as an engineer on troop and supply trains. Upon his return from war, Jeremiah and his wife came to Texas with their four Alabama born children. The family arrived in the fall of 1866.

When he arrived in Collin County, Jeremiah built a large log house, three miles east of Plano. He later built a town house on 14th Street in Plano so the children could be near church, schools and social activities. Before this move, the children attended the private Dublin School. Henry Dye and his brothers walked or rode horses to this school.

Following their father Jeremiah's death, Henry Dye and his brothers farmed, while Rebecca and the girls lived in town. In 1905 the log cabin burned, the townhouse was sold and Rebecca built a large white house which is still standing on East 14th Street just east of Los Rios boulevard. Six of Rebecca's children lived there with her. The last living child Emma lived in the house until she was 97 years old. When she died at age 103 she was the oldest living native of Plano. Henry Dye's twin sisters, Lou and Dru, can be seen today in a portrait hanging in the Heritage Farmstead Museum in Plano.

Henry Dye farmed until 1907 when he moved to Plano so that his children could attend school. He was a foreman of three gins - one was located across the street from where the First Christian Church of Plano now stands. He was also the night agent for the old interurban transit company, a rail system that ran from Waco north to Denison. Henry Dye and his wife, Belle Netzer were the parents of three children, Donna Belle Boggess, Mae Boggess and Henry Dye Boggess, Jr. His daughter Donna Boggess Harrington, was salutatorian of the Class of 1917. 

Donna married Robert Lee Harrington and they had two sons, Robert (Rob) Lee Harrington, Jr. (former Mayor of Plano), and Don Harrington, both of Plano. H. D. and his wife Billie, were parents of a son, Jeremiah (Jerry) Boggess of Dallas, and Sue Boggess of California. Rob, Don and Rob's children, Robin, Ginger, Bill and Suzan were Plano High School and Plano Senior High School graduates. Bill had two daughters, Tori and Heather.