As far as I now know, there was no family connection between Isham Bradley to the Haston family–but there is one possibility I will mention in a footnote later in this article.  Isham may have just been a close friend of David Haston and liked the Hastons so much that he just blended in with the rest of the Haston family.  Whatever the relationship was, it was strong enough for Isham Bradley to travel to the wilderness of middle Tennessee in order to settle adjacent to the Haston family (even before his bondsman-buddy, David, arrived in the area).  Isham’s name was on the July 22, 1806, petition to create White County, TN, but he seems to have struggled to settle down in White County.   He purchased 50 acres on the Haston Big Spring on August 28, 1807.   But he sold that tract to Charles Mitchell, just a year and a half later. 

In 1811, David Haston named his third son “Isham Bradley Haston,” who ended up living near where Isham Bradley lived in central Missouri.  And that was not the only time the first and middle names “Isham Bradley” appeared through the Daniel Haston family line.  David Haston’s son Isaac T. Haston also had a son he named “Isham Bradley Haston.”  I think it’s safe to say, Isham Bradley was well-liked among the Hastons (at least in his earlier years around them), even though he seems to have been a bit unsettled.
 

It appears that Isham Bradley moved around the county some, but in 1824, Isham Bradley and “Lady” were employed to superintend the business of Bell Tavern in Sparta.  Their credentials were described as: “long experience which they have had in this line of business, and the high reputation which they generally sustained with their friends and the public….”   But that employment didn’t seem to work out long for some reason.  And one time he was selected by the county court to be the keeper of the courthouse in Sparta, but the next day that decision was reversed for some reason.
Source: The Sparta Review, Wednesday p.m., September 15, 1824.

He moved back east, to Monroe County, TN before 1830 and stayed there for about ten years.  One Monroe County court record* stated that by 1840 Isham Bradley had “left the country” (probably referring to that local area) with his son-in-law, Henry Hobbs.  According to the 1840 Polk County, Missouri census, Isham Bradley lived adjacent to Henry Hobbs, in Polk County, Missouri.  The wife of Henry Hobbs was Juriah Bradley** Hobbs.  One of Henry and Juriah Bradley** Hobbs’s sons (and a grandson of Isham Bradley) was Isham/Isom Hobbs–probably born in White County, TN, and named for his grandfather.  Grandson Isham Hobbs was a desperado, a bold and dangerous criminal.

*Monroe Chancery Court Record, #124, Joseph Donohoo v. Charles K. Gillespie, Will Forester, Alexander Webb, and William Wooden

**According to the 1850 Census Juriah Bradley Hobbs was 56 years old.  If that is accurate, she was born about four years before Isham Bradley married Susana Matlocks.  Was Susana his second wife?  Was Isham Bradley married previously to one of Daniel Haston’s daughters who gave birth to Juriah, but died prior to Isham’s May 13, 1798 marriage to Miss Matlocks?  Was that Isham Bradley’s connection to David Haston and the Daniel Haston family?

In northern Polk County, MO (that became southern Hickory County, MO in 1845), Isham Bradley and Hiram Turk purchased land (on the same day) adjacent to each other.  Hiram Turk and his family were a bad bunch!  And the Henry Hobbs family was not much better.