Check this out: In 1860, in Clay County, Missouri, Frank and Jesse James are found living in the same neighborhood as my great great great Grandfather James S. Holt. [See 1860 Federal Census images below]. Jesse James and James S. Holt were the same age and would have gone to school together.
Also, by around 1910, still in Clay County, Missouri, James S. Holt’s son, Charles N. Holt (my great great Grandfather) can be found living just down the road from Frank James (Jesse James had been shot and killed in 1882). [See map below from around 1910 with the families highlighted]. I remember my great Grandmother (Charles N. Holt’s daughter, born in 1908) telling me stories of how she had to walk by the James farm on the way to school each day; you can see the school in the upper-left quadrant of the map below. Also note the property of Frank and Jesse James’ mother, Zerelda Cole James Samuel, just to the west of the Frank James property. Also highlighted on the map is W. A. Crossett, the nephew of my great great great Grandmother, Sarah Crossett Holt; Sarah was the wife of James S. Holt mentioned above.
There’s also a book that purports to show a link between James S. Holt and Frank and Jesse James. From page 65 of “Desperate Measures” by Ralph P. Ganis, 2007:
“Presumably, James S. Holt of Clay County was one of those most responsible for leading the [Jesse] James boys to North Carolina. Holt was born in March 1848 in North Carolina, the son of John and Minerva Pritchett Holt. He attended the old Bethel School [in Clay County] with [James gang member] Jim Cummins and the James boys, and his friendship with them was likely a critical factor in visits to North Carolina. James Holt’s aunt, Nellie Pritchett Vincent, lived in Thompsonville, North Carolina, and it was here that the James boys were said to have stayed [likely in about 1868].”
“Holt served as a Confederate soldier during the Civil War. His family moved from Rockingham County, North Carolina to Clay County, Missouri about 1850 or 1851 and settled next to the Cummins family in Washington Township, not far from the James farm. The Holts knew the Cummins family in North Carolina before moving to Missouri and were very close. James Holt became smitten with Jim Cummins’ first cousin, Sarah Crossett, and the two would eventually marry in 1872.”
And from page 69 of the same book:
“Two areas that were visited in northern Rockingham County [in about 1868] by the [James] boys were Spray and Mayfield. At Mayfield, they stayed at the home of John and Martha (McKinney) Walker. The Walkers had five sons who had served in the Confederate Army, two dying during the war. Mrs. Walker had extended family in Clay County, Missouri, and her niece would eventually marry Isaac Lee Pritchett, who was the nephew of Nellie and Minerva Pritchett; therefore, a first cousin of James S. Holt, a companion of Jesse James.”