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Uncle Milton was the son of William "Little Bill" Gregory, who came with his parents to Smith County
in 1791 from North Carolina. "Little Bill" Gregory died the first of November 1872.
Miss Matilda Grissom became Uncle Milton's bride about the year 1846. She passed away around 1865
and he never remarried. They were parents of four children, three sons, Wes, Isaac and Alex Gregory,
all prominent citizens of the Pleasant Shade area; and a daughter, Mrs. Wade Smith, also of Pleasant Shade.
A correction: There were 2 daughters the other being Laura Udora Gregory see Notes at bottom of page.
At the time of his death, there were nineteen grandchildren, fifty six great grandchildren, and seventeen
great great grandchildren. The oldest of the great great grandchildren, being nine year old Louzell Kittrell,
daughter of Mr. and Mrs. Lester Kittrell.
Milton Gregory was the last surviving member of a large number of brothers and sisters. His funeral was
conducted by Revs. C.B.Massey and Calvin Gregory.
Uncle was possessed of many virtues, being honest, frugal, thrifty and upright in his dealings. He worked
very hard nearly all his life, having helped to make a corn crop only two years before his death. He was
quite active for one of his years and could mount a horse as easily as men half his age. By means of his
thrift, he managed to lay aside a large amount of money which he loaned to hundreds of persons over this
and other counties. He never did any business with a bank and refused to take checks in payment for debts.
Since his death it is reported that a flour sack containing $8,000 was found in his home by relatives. His
wealth is estimated by some to be as high as $50,000.
Uncle Milton was what might be rightly called a pioneer of the county, as he lived very much like his
ancestors of a hundred and forty years ago. He lived in a large log house with the cracks chinked as in
olden times. Near the house stood the bee hives once seen around nearly every pioneer home. Instead
of the modern feed barn, there still stand the little log stables scattered here and there. The world's
modern ways did not disturb the peaceful trend of the life of this old man and he went about his way as
did his father before him. His memory of olden times was now and then good and he told of numerous
happenings of the long ago. He saw all the wars in which our country engaged except the two wars with
England, although he was never a soldier. He only had one picture made during his long life and that was
done to some extent without his knowledge of what was going on.
He was the last person in all this section to engage in what was called in olden times a "pitchedbattle"
which really meant a fight between two men in a ring with seconds to see that each man had fair play.
They were allowed no weapons and could use only what nature had provided. This was considered great
sport in Smith County a hundred years ago, but the tender young men of this day and time would not last
long in a scrap of this kind.
Uncle Milton fought one battle of this sort about seventy years ago when he was a man of about 28 years
and weighed about 160. However, he was all muscle and bone and was considered the most active man of
his section. In the neighborhood of Dixon Springs there lived a famed bully, by the name of Matt
McClanahan who had had numerous fights and had whipped nearly every man he had ever fought. He
challenged young Gregory to a combat and Gregory rather tried to get out of the fight as McClanahan
had more experience in such struggles and was noted for his strength and endurance. However, when the
fight could not be avoided without loss of honor, the two met in the middle of the pike at Dixon Springs
and the "battle" began. Back and forth the two men struggled with might and main, the advantages being
first with one and then the other. McClanahan was the larger man and might have been a little stronger,
but Gregory was the more active and quicker on his feet. Striking each other with all their force,
clinching, going down on the ground together the two men wrestled and struggled for some time. Finally
McClanahan managed to get his opponent down. Gregory struggled with all his power and strength to
come out from under the larger man. He was on the point of giving when a bystander urged him to strive
a little longer. With a last desperate effort Gregory turned McClanahan and together they rolled into a
ditch at the side of the pike with Gregory on top. With one free hand he grabbed a large handful of sand
and with all his force rubbed the sand into the eyes of his struggling opponent. This so blinded McClanahan
that he gave up the fight and concede the victory to Gregory.
The fierceness of the struggle may well be imagined by the fact that Gregory entered the scrap wearing a
brand new pair of heavy brogan shoes. When the fight was over, the soles were torn off, the seams were
ripped up and the shoes torn to pieces. Afterward they met again at Dixon Springs, but this time peacefully
and ate a large watermelon, never afterward holding any malice toward each other. Such things were
common in our country in pioneer times, but things of this sort have long since passed away.
(copied from the 1986 "History of Smith County, Tennessee")
Cal stated that Little Bill came to Tennessee with his parents from North Carolina. In numerous other reports,
Cal stated that Little Bill's father, John Gregory, had already died before the family moved to Smith County.
Cal also noted that Milton was the father of three sons and one daughter. However, the 1870 census shows
four sons and two daughters. His oldest daughter was Susan Missouri who married Wade Taylor Smith and
they became the parents of my grandmother, Laura Smith Dickerson. Wade Smith was the son of William
"Hairy Bill" and Minerva Smith Smith. The youngest daughter Laura Udora Gregory married Kenny Kemp.
Henry Milton Gregory's Setting Of The Stone
Milton and his wife, Matilda, had fieldstones as markers with no inscription. We placed the
stone between their two fieldstones located in the Gregory Cemetery on Frog Branch Road
The Stone Setters
Left to right John Waggoner Jr, Retta Waggoner, Tom Dickerson and Wife Faye and
Gordon Gregory with his son Dan in the next photo. Gordon owns the land the cemetery
is located on and Gordon is also one of Miltonís gg grandsons.
The Stone Setters