Tom as the son of Jesse Adam Chessor and Amanda Emma "Mandy" Bates. His first marriage was to Lucy Elizabeth Duncan; after the death of Lucy, Tom married Jessie Lillian Whitwell Chessor, widow of Charley Adam Chessor.

Tom and Lucy were the parents of 5 children: Candace Velera, Revo Hershal, Inez Elizabeth, Virginia Elvira, and Myrtle Irene.

“Good and Faithful Servant"
by James E. Chessor
[Obituary of Thomas Sidney Chessor,
May 7, 1879 - January 6, 1945]
"Well done, good and faithful servant . . . enter thou into the joy of they Lord."
(Matt. 25:21.)
Thomas Sidney Chessor, 65 died suddenly January 6th, at 9 o'clock a.m., following a stroke of paralysis early that morning. Death was attributed by the doctors in the Detroit hospital where he passed away to cerebral hemorrhage.
The only son of Jesse A. and Amanda Bates Chessor, he was born May 7, 1879, at the ancestral home on Hurricane Branch in the 9th District of Hickman County. Most of his life was spent in the same community in which he was born, and only in recent years had he lived on Russell's Creek in Perry County, and in Shipp's Bend near Centerville. For the past year he and wife had lived in Ecorse, Mich., where they were employed in a war productions plant. He was making preparation to return to the farm and rural life which he loved when Death called him to that Better Country, and to that "house not made with hands, eternal, in the heavens." Death may not be so bitter, after all, if in a glorious resurrection it is robbed of its sting and its victory, when the freed soul enters upon its eternal inheritance and the fuller, more abundant life -- "the life which is life indeed." He was one of the best known, as he was one of the most loved, of all the good citizens reared in the 9th District, and many, very many, good men have lived and died there.
He was first married to Miss Lucy Duncan, daughter of Billie Duncan, of the Flat Rock community near Hohenwald, October 18, 1905. To this union five children were born, all of whom survive: Candace (Mrs. Elmer Chandler) of Sulphur Creek, Revo Chessor of Cane Creek, Inez (Mrs. Willie Chandler) and Virginia (Mrs. Braden Wherry) of Shipp's Bend, and Myrtle (Mrs. Cayce Warf) of Council's Bend. He is also survived by 24 grandchildren, all of whom attended the funeral except Cpl. Wallace Chandler, who is in the marine corps in the South Pacific. He was preceded in death by his first wife, who died March 2, 1917, and by his parents and five sisters: Mrs. Josie Floied, who was drowned in Buffalo River together with an infant baby; Eliza, Leona, and Belle Chessor; Mrs. Nancy Floied. Three sisters survive him: Mrs. Tess Ora Floied, Mrs. Sarah Barber, and Mrs. Martha Brown, all well up in years, some years older than he. He was married to Mrs. Jessie Whitwell Chessor, widow of Charley Chessor, April 18, 1931, who survives him with four step-sons: Ray Chessor of Detroit, Raymond Chessor of Coble, and Clifton Chessor in the Navy and Leon in the Air Corps. (Leon came from Washington State by plane, but arrived too late for the funeral.)
Funeral services were conducted Tuesday, January 9, at 2 o'clock p.m., at the grave in the Chessor Cemetery on Sulphur Creek by John J. Lancaster, a life-long friend and a relative. One of the saddest features of the funeral was mentioned by Brother Lancaster when he recalled that in all the funerals which he had conducted there over a period of many years Tom Chessor had sung leading the hymns in a sweet, tremulous voice so well known to old and young of two generations, praising our Redeemer, strengthening our faith in that blissful Hereafter, brightening our hopes when "the earthly house of our tabernacle shall have been dissolved;" and now that voice is stilled on earth forever! Yet the redeemed sing the praises of the Lamb evermore where there are no discords of war and earthly trouble, but all is joy and peace!
He obeyed the gospel of Jesus early in life, and was baptized by W.S. Morton. He lived a consecrated life to the hour of death, walking in the footsteps of the Saviour every step. None knew him but to love him. A man of pure motive, living faith, of great patience and unfailing kindness, he will be sadly missed. Our loss is his gain. "Well done, good and faithful servant: thou hast been faithful over a few things, I will set thee over many things; enter thou into the joy of thy Lord."

This obituary is taken from Uncle Jim' s Letter No. 18, written in January 1945 by James E. Chessor. Uncle Jim sent monthly letters "to service men, workers in war factories and personal friends" during World War II.
In No. 18, Uncle Jim also printed several reactions of family and friends to the death of Tom Chessor:
"Brother Tom Chessor was a good man."--S.T. O'Guin.
"It hurts to think of Brother Tom being gone. I had no better friend. It lightens the burden to know that our loss is his gain."--J.J. Lancaster.
"My heart is so overburdened with grief I count it a privilege to write. It consoles me to know [he] was prepared to go."--S.T. Bates.
"We were shocked to hear of Tom's death. We lost a good man, and we know how to sympathize with his family. He will be missed so much."--J.W. Floied, and
daughters, Claytie, Tommy Belle, and Willie Matt.
"I had known him for a long time and I also counted him as one of my very best friends. He was such a good man; and that cannot be said of but a few men. He was so much interested in the church and in everybody being just what they professed to be. His passing saddens me."--Robert Fain.
As Uncle Jim noted in his introduction to the obituary, he and Tom were double first cousins. Their fathers, Jesse and Adam Chessor, were brothers, as were their mothers, Amanda and Lucy Bates.