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His father, Jesse, "disappeared" (never to be found) circa 1826 leaving his mother, brother (Henry),
himself, and three unnamed sisters. They endured many hardships according to family stories passed down.
His mother remarried William Cannaday prior to 1840 and produced three more siblings.
His half brothers and sister were: Lacretia Ann (Creasy Ann) born circa Jan 1838; William
Balin (ca. 1840 - ca 1863/64); and Wade Kenneday (ca. 1843 - ?).
Sidney married Rebecca Knight ca. 1843 or 44. To them were born: Newton (3 Aug 1845 - 6 Mar 1934);
Jasper (ca. 1847 - ?); Manerva C. (9 Nov 1848- 14 Sept 1938); Louisa J. (19 June 1851 - 26 Jan 1950);
Robert (13 Nov 1853 - 13 Nov 1934); William H. (May 1857 - ?); and Wade H. (20 July 1859 - 15 Nov 1948).
Sometime after 1871 Rebecca disappears from sight. Her fate and burial site are unknown at this time.
Sidney married Marinda (Rindy) Coombs in 1886. She was born circa September 1843 in Kentucky.
Creasy Ann Cannaday married James Clay (date unknown). In 1900 she was living in Sidney's household.