The 99th Pursuit Squadron, later dubbed the Tuskegee Airmen, was activated in March of 1941. In honor of this important anniversary I was drawn back to my own research and I found a possible connection to the prestigious airmen in my paternal Holbert line. Of course, with every new discovery there are always more mysteries that come along to challenge your findings.

Much of my research of the Holbert family reveals a long line of educators, and that tradition continued in the line of my 2nd great grand uncle, Benjamin D. Holbert. On the census records from 1870 and 1880 he is listed as the son of Franklin and Susan Holbert, living in Cherokee, Texas. In 1890 I found a city directory from Waco, Texas that lists a Benjamin D. Holbert as a colored teacher. The only record I found for anyone matching his birth date in 1900 was in the U.S. Jail in Muscogee, Oklahoma, Indian Territory. It states he was born in Texas and both of his parents were born in Alabama, which matches my uncle, but it lists his occupation as “physician”. This census also states Benjamin has been married for 13 years. Although I don’t find any more records for him after 1900, there is a marriage record for a B.D. Halbert and Annie Marie Estell in nearby Mclennan, Texas dated December 29, 1886 (14 years from that 1900 census). Coincidence?

Ann Marie Estell was born in Waco, Texas around 1868. I do not find her on a 1900 census, but I do have a city directory from as early as 1902 that puts her in Waco, Texas. In 1910 she is living in Hill County, Texas with four children: Annie, Benjamin Jr, Jessie and Ruth. All of the children’s death certificates confirm their father’s name as B.D. Holbert.

The only son, Benjamin Jr., is living with his wife, Sarah, on the 1928 city directory in Dallas, Texas. He is using the initials B.D. Holbert from this point forward. However, on the 1930 census he is now living in Seminole, Oklahoma. He is widowed and is boarding in the household of William and Emma Simmons. His current age, age at first marriage, and his occupation of public school teacher match my ancestor’s information. On the 1940 census he is still in Seminole, Oklahoma but is now married again and a principal in the public schools. Was that an error to list him as widower on the last census? If so, why was he living apart from his family?

Sarah Cummings Holbert is still living in Dallas, Texas with her two children, Bertrand and Kenneth, on the 1930 census. She also states that she is widowed. According to her death certificate she had remarried and was now Sarah Sears. I have not yet been able to find her or her children on the 1940 census, but I do know that she was also a public school teacher.

It is Benjamin and Sarah’s son Bertrand Holbert who was a member of the Tuskegee Airmen Class 45A Single Engine Pursuit Pilots. I don’t have the proof I would need to make this a positive match even though there are relatives who have listed them in their family tree. I have so many ancestors named Benjamin, B.D., and Annie to keep them all straight. I need to order the death certificates of all the names that I don’t have already, and hopefully they will clear up some of the confusion.

Tuskegee Airmen Class 45A Single Engine Pursuit Pilots

That would be my cousin Bertrand Holbert, 2nd row, last one on the right.

Photo retrieved from http://www.military.com/Content/MoreContent1/?file=BH_Tuskegee