David Gregory reportedly ran away from home at a young age (around ten or so) and further contact with his family was lost. Family lore claims that David's father, concerned about his well-being, determined David's whereabouts, and after being assured that he was safe and taken care of, returned to Canada without David.
It is thought that Charles W. Warner is David Gregory's half-brother.
David Gregory was enumerated with John and Mary Young in the 1870 Census in St. Clair County, Michigan.
David was a real estate agent. David and Martha moved from Michigan to Colorado, where Ivy and Albert had a homestead, and either purchased the rights to or homesteaded land about a mile and a half from the Trudgeon farm. At some point, they sold their property and returned to Michigan. They later spent some time in Florida prior to moving to Oregon.
"David Gregory Dies -- David Nelson Gregory passed away at his home, Fourth and Grant streets, this city, at 2 A.M., Saturday, April 28, 1928, aged 80 years, 5 months and 29 days. He was troubled with Bright's Disease and paralysis, had been ailing for five years and was bedridden three months. He was a man highly esteemed by those who knew him and was the last of 12 children to go.
Deceased was born near Quebec, Canada, November 29, 1847, and from there moved to Charlevoix County, Michigan, where he resided 40 years. There he married Miss Martha H. McKee. From this union there were three children, one of who died in infancy. With family he came to Woodburn in November, 1926. Surviving him are his wife, two daughters, Mrs. A. J. Trudgeon of Woodburn and Mrs. Ethel Tuttle of Montana, also 11 grandchildren and 2 great-granddaughters.
Mr. Gregory was a member of the Church of God, in which church in this city funeral services were held at 11 A.M., the pastor, Rev. John L. Green, officiating. Music was by Miss May Stewart and Mrs. John T. Myers with Miss Ruth Shrock at the organ. There were floral tributes from friends. Interment was in Belle Passi cemetery. The pallbearers were Will Livingston, John Shrock, Dan Shrock, N. B. Myers, Mr. Rice and Mr. Dickey."
David and Martha had three children: Ivy, Ethel, and a baby girl who died as an infant. Census records (1900) show a son, Arnold Gregory, residing in the Gregory household. Oral family history recalls Arnold was "found in the woods" and taken in as part of the family. It is also recalled that he was mentally "not right" and almost killed his mother, Martha, and was then "sent away." Records from the State Archives of Michigan show that Arnold was admitted to the Traverse City State Hospital on January 23, 1912. He was stated to be "without psychosis" and "mentally deficient." The records show that he "eloped" (escaped) three time and was brought back each time. David Gregory is listed as Arnold's "foster father." Arnold was never released and died in the hospital of tuberculosis at age 35 on January 1, 1928.