The following data is extracted from The Indian Territory, Its Chiefs, Legislators and Leading Men.
Pilot Grayson was born in 1852, within two miles of Eufaula, son of James Grayson, of the Creek Nation. It was not until the close of the war that Pilot began attending the neighborhood school, which he continued for the space of two years, moving from thence to Cane Hill College, Arkansas, where he remained several sessions. Returning home, he afterward went to Howard College, Alabama, where he spent one session, and from thence went to La Grange College, Missouri, where he continued his studies for two years, and thus completed his education. Pilot commenced life in the capacity of a schoolteacher, and taught in the Creek Nation for about five years; but his health began to fail and he concluded to try farming for a while. Meantime he was appointed examiner on the National School Board, which office he held for four years. Soon after this he embarked in the mercantile business in Okmulgee, the capital of the Creek Nation, in partnership with D. A. Carr, which he continued for two years, until, selling out, he returned to Eufaula and farmed for a few more years. Again he went to Okmulgee, this time to clerk for Messrs. Harrison & Carr, but did not sojourn very long there, returning to his home and his agricultural pursuits, where he spent another two years. Not long afterward Mr. Grayson opened a mercantile house at Brush Hill, northwest of Eufaula, which business he is still carrying on. In September 1891, he purchased Dr. K. R. Cutler's mercantile interests in Eufaula, and now personally manages the house, which has a very extensive trade. In December, 1882, Mr. Pilot Grayson married Miss M. F. Buckner, daughter of the Rev. H. F. Buckner, but, unfortunately after being married but one year and three months, his wife died, leaving one child, a boy, born in January, 1884, and named CC. W. Grayson. In March 1887, he married Mrs. A. Buckner, of Eufaula, widow of the Rev. Dr. Buckner. Mr. Grayson is owner of a good farm of 250 acres, west of town, besides a small stock of horses, cattle and hogs. In his Eufaula store he carries a $6,000 stock of merchandise, and is a man of good business qualifications, of pleasant address and an education far beyond the average. He is a member of the Baptist Church and the Masonic order.
Source: The Indian Territory, Its Chiefs, Legislators and Leading Men