In the middle 1850s, Thomas Rutherford Dailey, Henry H. Dailey, their sister Permelia, and her husband, J.C. Keen, moved fromAttala County, Mississippi, to Texas, and brought a number of slaves with them. Henry H. Dailey, his wife, Julia Dean Dailey, and son Jack, settled near the Brazos River in Brenhem. Thomas R. (1802-1876), his wife Behethia (1801-1859), four sons: Tandy W. (1828-1867), Milton Dickerson (1829-1863), Gus (1832-c. 1864), and William A. (1834-c. 1864) settled on the Garrison Greenwood League in Houston County. A deed from Joseph C. Kerby to Thomas R. Dailey is dated July 27, 1855. Also settling with them inHouston County were Joseph C. and Permelia Dailey Keen and their son Silas E. Two of Mr. Keen’s children by a previous marriage also accompanied them—Thomas J. Keen and Harriet Keen White who was married to John Banks White, a nephew of the Daileys. Mr. Keen was a blacksmith and his skills were in great demand to the agricultural settlers of the community. On the first Saturday in July A.D. 1853, a church was organized that would later be known as the Daly’s Baptist Church. In a deed dated November 28, 1859, T.R. Dailey deeded ten acres of Greenwood land to be used for a cemetery and church. A post office, named Daly’s, Texas, was established June 22, 1876 and Goodridge B. Moore was appointed the first postmaster. Thomas Rutherford Dailey built a frame house in 859. A sawed rock from the chimney of that house is inscribed “1859”. On December 1, 1859, Behethia died and was the first buried in the “Old Dailey Family Cemetery.” On June 29, 1861, the Captain R.S. Pridgen Co. Mounted Horse Division (also called Elkhart cavalry) was sworn in at T.W. Dailey’s store. T.W. Dailey, S.E. Keen, W.A. Dailey, M.D. Dailey, Daniel Dailey, T.R. Dailey, and Thomas J. Keen are listed in the roster. Family tradition says that Thomas R. enlisted that day to go to headquarters inSan Antonio to offer his services in the Confederate army in the stead of his son Milton who was married and had three young children. The army refused his offer but he kept his promise to his oldest grandson Tommy and brought him a “pacing pony” when he returned. Jack Dailey, son of H.H. and Julia Dean Dailey, Silas E. Keen, son of J.C. and Permelia Dailey Keen, Gus, and Bill Dailey were killed in the war. Milton died of wounds and illness on his way home in 1863 to see his baby daughter, later known as “Miltie”. He was buried at Boggle Depot, Oklahoma Indian Territory. Only Tandy returned to the Greenwood League home. Milton Dickerson Dailey had married Caledonia Isabella Beazley (1838-1895), daughter of Charlie and Thursa Hyde Beazley on July 27, 1852. Their children were Thomas H. 1(1854-1931), Thursa Adelaide (1857-1941), Charles Beazley (1859-1903), and Emma Catherine (called “Miltie” after her father’s death) (1862-1941). Thomas H. was married to Jessie Meriwether. They had one daughter, Etha, who married Dr. E.A. Means of Dallas. They had no children. T. Adelaide “Addie” was married to George W. Mobley and they had no children. Charles B. Dailey married Ruth Ann Edens. Their children were Thomas F., Iva J., Henry H., Balis Edens, and Robert Smith. Two other sons died in infancy; Iva, a victim of typhoid fever, died at twenty-one. Emma Catherine was married to James A. Hill. Their children were Addie, Nell (Mrs. Frank Rhea), Callie (Mrs. C.L. Walters), Charles C., Daniel Forrest, Mary Belle and James A. In January, 1867, Tandy Dailey, the only Dailey son who survived the Civil War, died and was buried in the family Cemetery where his mother had been buried. The Masonic emblem on his tombstone bears silent testimony that he was a member of this worthy organization.

Thomas Rutherford Dailey lived at a time when horses, wagons, and navigation on the Trinity River were the main ways of transportation in this area. So when there was prospect for the International and Great Northern Railroad to come through the Grapeland area, he donated two hundred acres of land out of the Garrison Greenwood Survey for this project. He died August 13, 1973 and was buried beside his wife Behethla. In his will, recorded in Deed Record Book 186, page 350, in Houston County Courthouse can be seen the touch of tenderness and love for his second wife, Mary Ann Shotwell Dailey, and his stepsons Emmett and Jim Shotwell. He made provisions for the education of his grandchildren, the offspring of Caledonia and Milton Dailey. He appointed his brother, H.H.. Dailey, administrator of his estate showing the close relationship of the two brothers. This close relationship continued to exist among his four grandchildren and down through the years to the present generations. Members of later generations include: Charles Beazley Dailey (1859-1903) married Ruth Ann Edens (1858-1950) .

Their children were an infant who died at birth; Charles Milton (1881-1882); Thomas Franklin (1883-1944); Iva Josephine (1885-1906); Henry H. (1887-1934); Balls Edens (1891-1979); and Robert Smith (1896-1978). Thomas F. Dailey married Elizabeth Kent (1886-1938). Their children were Charles Thomas who first married Zilpha Haskins; their children were Charles Lewis, Elizabeth (Mazie), John Haskins, and Mary Louise. Then Charles Thomas married Carolyn Darsey. Liston Dwight married Maudine James; their children were Balls Edens, Helen Maurine, Elizabeth Lynn (Becky) Peggy Jean, Lista Sue, and James Dwight. James Hill married Pauline Barefield and they had one daughter, Jacqueline. Mary Ellen married Henry Bell Spindle and they had one son, Henry Bell Jr. James Kent married Hazel Scarborough; their children were Joyce Ann and James Kent, Jr., Iva Tom (1918-1919) lived about fourteen months. Dan David married Sue Towery; their children were Sharon Sue, Elizabeth Anne, Deborah Ruth, and Dan David, Jr. then Dan David married Loraine “Mick” Marmande. Thomas Franklin, Jr. married Joy Ann Hoherd (1932-1954) and they had one daughter, Linda Beth; T.F. Dailey, Jr. married Frances Ivey; their children were D. David and Michael John. Henry H. Dailey married Mary LeotiKent (1889-1957). Their children were I. Irene who married Dennis Frazier; their children were Douglas  Gene and Henry Lee; Frank Cummings who married Lorena Callaway; they had no children. Henry H., Jr. married Ouita Skidmore and their children were Carmen Leoti, Ruth Ann, Henry H. III, and Thomas Rutherford. Tom Kent Dailey was the youngest child born to Henry and Leoti. He never married. Balis Edens Dailey married Bulah Pool (B. 1894). Their children were Iva Helen (1922-1930), Jo Ann who never married, and Balis Gene who married Jack Wright Shoultz. Jack and Gene have two daughters, Sue Anne and Jo Ellen. Robert Smith Dailey married Florence Pennington. Their children are Robert Milton who married Dorothy Lou Woodruff; their children were James Robert, Glenda Kay and Mitchell Milton. Florence and Smith had an infant son who lived only one day. Geraldine, their daughter, married Don McReynolds; their children are Randy Craig and Cynthia Ann.  Emma Catherine Dailey married James A. Hill (1852-1894). These descendants are found under the Hill Family history.