Sources: https://www.familysearch.org/ark:/61903/1:1:MDZS-SMT and familysearch.org, wikitree.com, findagrave.com
According to the US census of 1850, Jefferson William "Roy" Gillispie was 10 years old at the time of the census, which means he was born in 1840.
His father Wilson Gillispie died on July 4, 1836 and his mother Mary Gentry Gillispie Boggs remarried in 1843.
Per the 1850 US census, Jefferson was living in Missouri with his mother, Mary Gentry Gillispie Boggs, age 43, (age in 1850) and stepfather Robert Robinson Boggs, age 33 (age in 1850). and numerous siblings as well as Thomas Hart and his wife Nancy Jane Gillispie Hart, their 2 year old and newborn child. Nancy Jane was Mary Gentry Boggs daughter with Wilson Gillispie. Nancy Jane and Thomas Hart were saving to buy their own farm.
According to Findagrave.com, Jefferson William "Roy" Gillispie was born May 16, 1840 and died June 20, 1908. Tombstone engraving states 1840-1908. The biblical record published on Mary Gentry Boggs findagrave biography states his birth year as May 1834 which is not possible because another sibling - Sarah Ann Gillispie - was born in April 24,1834, less than one month prior.
Jefferson married Almyra Hansberry In 1869. Almyra was born in 1846 in Indiana and died in 1927 in Norton County, Kansas according to her findagrave memorial. Both are buried in Norton Cemetery, Norton, KS.
They had 2 children, Nellie Gillispie - born in 1871 and died in 1937. She married a man named Anderson according to the engraving on her tombstone at findagrave but there is no link to husband to know the name.
Their son Ola (Ollie) T. Gillispie was born in 1872 (according to the engraved tombstone at findagrave.com) but the biography states 1873 which is incorrect. The tombstone date is correct. The 1920 US Census shows Ollie to be 49 years old and living in Jewell, Norton County, Kansas. The 1920 census also shows his mother Almyra Gillispie living with Ollie in Jewell. The other information on census form is accurate, that Ollie was born in Kansas, His father was born in Kentucky, and his mother Almyra was born in Indiana so this is the correct Ollie Gillispie even if the birthdate is off by one year. He never married.
https://www.familysearch.org/ark:/61903/1:1:MFX3-V57