↑#Will-Penny-1339 This Jesse is by definition the one from Edward Penny's will. The birthdate is a guess based on 1740 for Caleb and assuming birth order as listed in the will.
Sources
Will-Penny-1339: Last Will and Testament of Edward Penny, Johnson County, North Carolina, Dated 20 Jun 1779, Proved ?? (Nov 1782 was given without a source)
North Carolina, Wills and Probate Records, 1665-1998 (Ancestry.com)
James Penny, Jesse Penny, Elizabeth Penny, Edward Penny, & wife Elizabeth Penny given specific bequests. Caleb Penny, Charles Penny, Parnuwell Penny, James Penny, Martha Jones, Jesse Penny, Mary Utley, Elizabeth Penny, and Edward Penny are listed as children. Signed Edward Penny.
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DNA Connections
It may be possible to confirm family relationships with Jesse by comparing test results with other carriers of his ancestors' Y-chromosome or mitochondrial DNA.
However, there are no known yDNA or mtDNA test-takers in his direct paternal or maternal line.
It is likely that these autosomal DNA test-takers will share some percentage of DNA with Jesse: