Throughout his travels, Charles Cocke was always accompanied by a Jester Cocke. This was true in Lee County, Virginia, in Wayne County, Kentucky, and in Clark County, Arkansas. However, it appears that these were not necessarily the same Jester Cocke, but were father and son. In 1799, Jester Cocke, Sr. sold his property in Lee County to his daughter Rebecca and her husband James Fitzgerald. He then moved to Kentucky and settled into what later became Wayne County, Kentucky. Charles joined him a few years later. Jester Cocke, Sr. may have also preceded Charles to Madison County, Alabama. There is a listing that shows a "Lester" Cocke living in what was then Indian territory. (One source of confusion is that Jester Gwinn Cocke also married a Sarah, and they continued to show up in the Wayne County records until 1830.) There is an unidentified Jester Cocke who died in Monroe County, Mississippi in 1839. He is mentioned in a court case and appears to have been associated with the family of William Cocke from Tennessee, a descendant of the Cockes from Henrico County, Virginia. This might have been Jester Cocke, Sr.

The Jester Cocke who accompanied Charles Cocke to Clark County, Arkansas was Jester Cocke, Jr. This is shown by his age in the 1830 Census.

Jester Cocke, Sr. is said to have had a brother Jacob Cocke. They both moved to Kentucky in 1799. However, very little is known about this Jacob Cocke.

Jester Cocke, Sr.
b. cir 1750
m. Sarah Cole, 1770
   Possible parents: James and Ave Cole
Children:
   i. Jester Cocke, Jr.
      b. 1773
      d. 1852, Clark County, AL
      m1 Mary, 1797, Lee County, VA
      m2 Cynthia, ca 1823
         b. 1803, GA
  ii. Rebecca Cocke
      b. cir 1778
      m. James Fitzgerald