Jesse Fly - Fly Family Founder, Illinois
Son of John Fly and Unknown Wife
6. Jesse Fly 4 (John 3, Jeremiah 2, William 1)
This man may be the
most mysterious of all the members of the early Fly family.
He did live in
May 30, 1759.
Isle of Wight Co.,
This indicates that he was probably born about 1738; although under aged people were able to sign as witnesses if they were close to age twenty-one.
He lived in Isle of Wight Co. for the next fifteen years and was involved in a court case:
April 1, 1773.
(IoW Order B. ________Page 148)- not found (FGF)
Friday Sept. 3, 1773-page 183
Jesse Fly, Pltf., against Ann Eley & Thomas King Exors. of John Eley, decd, Defts.
Continued until next court (IoW Order B1772-1780, 183)
The case continued, but Jesse could not provide anyone to give the court assurance that Jesse’s court costs would be paid:
Friday Jan. 7, 1774.
Jesse Fly, Pltf., against Ann Eley & Thomas King Exors of John Eley, Dec, Defs.
Upon the mottion of the defendants by their attorney. It is ordered that unless the plaintiff shall find sufficient suretey for the costs of this suit at the next court that the said suit shall be dismissed. (IoW Order B1772-1780, 239)
Ordered that Ann Ely & Thomas King Executors of John Ely deceased pay unto Elias Hering 390 pounds of tobacco for six days attendance and travelling twenty miles four times as a witness for them at the suit of Jesse Fly (IoW Order B1772-1780, 251-252)
April 14, 1774.
Order Book 1773-1777, p. 351
Ann Eley & Thomas King Extors & c
Of John Eley deced……………………………} Plt upon an attachment
Ann Eley & Thos King Extors & c of John Eley having obtained an attachment against the estate the Jesse Fly who hath privately removed himself or – absconded that that the ordinary process of the law cannot be served upon him for a debt due from the said Jesse Fly to the said Ann Ely & als Charles Briggs Gent Sheriff now made return that he executed the said attachment in the hands of Jos (?) Mounfort and Elisha Fly and that he had summoned the said Jno (?) Mountfort and that he had summoned him as _________ who being sworn deposed that he hath ________ belonging to the estate of the said defendant and Three pounds subject to a constable attachment _______ Kellas fee 16/3 and 2/16 costs also the sheriffs (fees??) levys 9/16. (Interlining unreadable here….) It is considered by the court First they---------- recover agst the said defendant Eight hundred and forty six pounds of tobacco and fifteen shillings. Ordered that the garnishee pay the Balance in his hands towards satisfying the said judgment and that an attachment be issued against the other garnishee 
Jesse probably went
6a. Jesse Fly 5 (Jesse 4, John 3, Jeremiah 2, William 1)
Delaney Whitford in
Eliza Jane was born to them in 1810 followed by John Dickerson (1812), James Whiteside (1814), Sarah Delaney (1816), Martha K. (1818), Jesse Jackson (1821), Madison Perry (1824) and Christopher Columbus (1827).
The next appearance of a Jesse Fly was in militia list for the War of 1812:
Capt. Kincaid's Co.-#34
Jesse Fly, #35
John D. Fly,
Capt. Kincaid's Co.- #34
Jesse Fly, #35
John D. Fly
#1594 John Fly
Capt. Kincaid's Co.- #34
Jesse Fly, #35
Fly, #1594 John Fly
Jesse seems to have
been close to
John Dixon Fly in
May 24, 1814. John D. Fly, decd. inventory of his estate includes accounts on Lemuel Lawrence, William Rutherford, John M. Wright, John Johnston, & Jesse Fly. Signed by John Fly, Admin. & Sally Fly, Admrx 
He also purchased some items at the estate sale:
Aug. 29, 1814. John D. Fly- Estate sale. Purchasers: Sally Fly, Jesse Fly, Jesse Marton, Robert Thompson, John Beves, John Fly, Michael Goodwin, Elisha Fly, John Collins, William Harris, Alfred Wallace, George Hartman, James Hill, Russell Sullivan, Godfrey Shelton, Daniel Mitchel, Abraham M. Degraffenreid, Enoch Ensley, Joshua Cutcheon, Isaac Battle, Jordan Barnes, William Griffin, James Kincaid, Charles H. Cody, Thomas Hill, Henry Seat, Azariah Jones, William Harwood, Edward Collins, Thomas Shelton, John M. Wright 
In 1815, he purchased land. If he owned land before this, it was not recorded:
July 18, 1815.
George W. Wolfe of Davidson
Co. sells to Jesse Fly
of Davidson Co. for $ 60, 30 acres in Davidson and Rutherford Cos. on
the waters of Hurricane Creek, a branch of
Rec.: July Session, 1815 
He then witnessed a
Will of James Wright, decd.
Witness: John Buchanan and
Proven Nov. 22, 1816 
The land that he purchased in 1815 was sold in 1818 at a profit:
June 8, 1818. Jesse Fly sells to Josiah Seat for $150, 30 acres in Davison and Rutherford Cos. on the waters of Hurricane Creek. 
Apparently Jesse was
planning on living in
Jesse soon moved to
Samuel McCracken is
credited with having been the first one to settle within its’ present
limits. He came it is
believed in the year 1823, from near
Jesse and Sarah Fly, and their five sons—John, Jackson, James, Perry and Columbus, also their three daughters--- Eliza, Sarah and Martha, came about the same time as McCracken, Jesse put up a horse mill and ran it for several years. It was, in later years…. Jesse moved his family from Wayne Co. Ill to Union Co. Ill. and settled in the Water Valley settlement east of Cobden Ill---- here he was a farmer, cabinet maker, and for many years a minister of the Christian Church in Water Valley.
Jesse Fly was a volunteer in the war of 1812 in the Battle of New Orleans under General Jackson.
Jesse moved all of his family to Union Co., Illinois before 1850 there were no Flys listed in the 1850 Census; only McCracken. 
Between 1830 and
1840, Jesse moved from
By the time of the
1860 Census, seventy year old Jesse was living with John Fly.
His wife, Sarah, had died on Feb.
17, 1859 according to her tombstone in
It is not clear where Jesse Fly was living in 1870. The 1870 Census does have a Jacob Fly (79) living in the household of John Fly (57). The name is clearly not Jesse, but there was no other Fly male of such advanced age in the state at the time. The household consisted of: John Fly (57), Susan (55), Julia (24), C. Caleb (18), Wm P. Jones (29), as well as “Jacob”.
Jesse died on April
The court records of
Children of Jesse Fly and Sarah Delaney Whitford Fly
6a.-i. Eliza Jane Fly 6 (Jesse 5, Jesse 4, John 3, Jeremiah 2, William 1)
This daughter was married twice, but died at the age of thirty five. She was first married to John McCracken; probably about 1830, but he died in 1835. Apparently there was at least one child, John C., born in 1833.
Eliza then married Alexander Nesbit at an unknown date. Eliza reportedly died in 1845 and it is not known if there were any children with Nesbit.
6a.-ii. John Dickerson Fly 6 (Jesse 5, Jesse 4, John 3, Jeremiah 2, William 1)
This first son was
born on Dec. 12, 1812 in
They were the parents of: Marcus Lafayette (1833), Catherine (1834), William Riley (1840), Martha Julia (1845), John T. (1857), and James M. (1861).
John died on Nov. 23, 1888.
6a.-iii. James Whiteside Fly 6 (Jesse 5, Jesse 4, John 3, Jeremiah 2, William 1)
Farmer about 1830 and they were the parents of: Atlena (1831) Isaiah
Lacey (1837), Louis (1836), Mary (1838), John Damron (1839), Mary Martha
Apparently, Kezia may have been married before her marriage to James Whiteside Fly. On the 1860 Census, James (42) was listed with Cassius (38), Allan Farmer (31), James Farmer (16), Harrison Farmer (12) and Mary Farmer(9). Perhaps James Fly and his wife were living with Kezia’s siblings. Or these were Fly children erroneously called Farmer. This is not clear and further research may shed more light.
James W. Fly died on
May 28, 1901 in
6a.-iv. Sarah Delaney Fly 6 (Jesse 5, Jesse 4, John 3, Jeremiah 2, William 1)
Sarah was born in 1816 and she married John James Deming about 1833. They were the parents of: Elmyra (1838), Sarah Ann (1840), John Treat (1843), Martha (1844), William Jasper (1845), and Young( 1849).
Sarah died on June 24, 1886 and her husband reportedly died on Dec. 15, 1890.
6a.-v. Martha K. Fly 6 (Jesse 5, Jesse 4, John 3, Jeremiah 2, William 1)
Martha was born
about 1818 in
Martha became a widow and then married James R. Cochran by 1860. She is said to have died on Jan. 25, 1870.
This family is not traced further.
6a.-vi. Jesse Jackson Fly 6 (Jesse 5, Jesse 4, John 3, Jeremiah 2, William 1)
Jesse was born on
Aug. 17, 1821 in
Jesse J. Fly died on Feb. 25, 1904 in Mt. Vernon, Illinois. According to the 1880 Census, he was an undertaker. He had also served in the Civil War. According to his tombstone, his wife Mary died on May 10, 1909.
6a.-vii. Madison Perry Fly 6 (Jesse 5, Jesse 4, John 3, Jeremiah 2, William 1)
This son was born on
July 11, 1824 in
He was a farmer and
also served in the Civil War on the Union side.
He died on Oct. 23, 1890 and is
Jesse Jackson Fly, the oldest child of Madison and Sarah, wrote a letter in 1923 describing what he had learned about the Fly family.
6a.-viii. Christopher Columbus 6 (Jesse 5, Jesse 4, John 3, Jeremiah 2, William 1)
Jesse Fly’s last
child was born on February 21, 1827 in
He was drafted for
the Civil War, but his service record has not been found.
As an adult he worked on the
He and Martha adopted a child by
the name of Walter Vanfossen.
Wal was listed with the Fly family
in the 1880 census.
Christopher and Martha were
apparently taking in railroad workers as boarders in their house.
Apparently, he died on July 11,
Jesse Fly Descendant Tree
6. Jesse Fly (ca.1738-ca.1789)
a. Jesse Fly (1789-1872)
m. Sarah Delaney Whitford, 1808
6a.-i. Eliza Jane Fly (1810-1845)
m. John McCracken, ca.1830
m. Alexander Nesbit, ?
6a.-ii. John Dickerson Fly (1812-1888)
m. Sarah (Muzzie) McCracken, 1829
6a.-iii. James Whiteside Fly (1814-1901)
m. Kezia Farmer, ca.1830
6a.-iv. Sarah Delaney Fly (1816-1886)
m. John James Deming, ca.1833
6a.-v. Martha K. Fly (1818-1870)
m. John Parrish, ca.1840
m. James R. Cochran, ca.1860
6a.-vi. Jesse Jackson Fly (1821-1904)
m. Mary Elizabeth Baugh, 1845
6a.-vii. Madison Perry Fly (1824-1890)
m. Sarah Jane Asa, 1844
6a.-viii. Christopher Columbus Fly (1827-1898)
m. Martha Jane Camp, 1846
 Isle of Wight Order B1772-1780, p.109
 Southampton Co., Virginia: Order Book 1773-1777, p. 351
 Letter of Wally Fly, undated
 Letter of Ralph Hill, undated, Davidson Co. Militia Lists War of 1812
 Davidson Co.,
 Davidson Co.,
 Davidson Co.,
 Davidson Co. Tennessee Wills page 101.
 Davidson Co.,
 Letter From Wally Fly. Source: History of Wayne Co., Il Chapter xxii.