| Isaiah and Penny Chester were the parents of six children. They were, Leanna Malinda, Henry, Charles, Maurice Isaiah, James and Arcie Lee |
| Family History |
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| Isaiah Chester (1855)-(1939) Penny Bryant Chester (1868)-(1918) There are no picture available of Penny |
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| The Chester Family History & Family Tree |
Isaiah was born (a slave) in 1855. Penny Bryant was born (free) in 1868 the year the United States
Congress added citizenship to new freedom of the recently freed African American-Americans. Isaiah
became a farmer, and sharecropper. He started out as a young man, working on the “Hughes Overby”
Plantation in Steward County in western Georgia near the town of Omaha on the Alabama state line.
He was ten years old when the Civil War ended in April 1865. Congress declared an end to his
enslavement with the passage of the 13th Amendment in that year. Isaiah was ten years old, and
finally free in the land of his birth..
After the war, and the releasing of the slaves, Isaiah and his family elected to continue, and stayed, on
the same plantation where they had been enslaved until they finally moved on to Andersonville,
Georgia about twenty-five miles to the east in Sumter County north of Americus.. There the family
continued farming as sharecroppers on the A. B. Brown Estate. Their crops included cotton, butter
beans, sugar cane, peaches, and pecans.
They had ten (10) children living as of 1910. We have information on six children: Leanna Malinda;
Henry Madison (“Doc”); Charles (“Chum”); Maurice Monroe (“Son”); James Wesley {“Plute”); and
Arcie Lee.
We don’t know anything of Isaiah’s parents, or any siblings he had. We believe he had siblings,
however, because in the extended family was Horace, and Grover Burr who were cousins to Isaiah’s
children. Henry Madison son of Isaiah, Horace and Grover looked so much alike they were often
called “triplets,” though they were known not to be siblings at all. It seems clear Isaiah Chester had at
least two sisters since Grover and Horace were not brothers. Further, Isaiah’s siblings were likely
sisters since neither Grover, nor Horace carried the family name of Chester.
The family migrated north one by one beginning with Maurice, the fourth child. He brought with him
his wife, Beulah (“Kudda”) and their two daughters, Alma and Ruby. They moved to the Manchester
Area of the north side of Pittsburgh, in Allegheny County Pennsylvania.
The exact order of the family’s migration north is not certain. Maurice Monroe “Son” is believed to
have been the first. However, those who came first sent back for the others. For a while, Isaiah and
his two youngest children, Arcie Lee and James Wesley, lived with Henry his second-born, and his
wife Bertha Cunningham Chester in a section of north side called Woods Run in an area called “The
Pocket.”
Isaiah died in Pittsburgh in 1939 at the age of 84. There is no information on Penny Bryant Chester
after Sumter County, Georgia. Isaiah is remembered as a quiet man with a deep love of music and
enjoyed spending time harmonizing old hymns with his sons. Penny is remembered as being a small
beautiful woman with long black hair, who wore a size 2 dress, and had very small feet. She is best
remembered for her mild and gentle personality, and quiet disposition.
Congress added citizenship to new freedom of the recently freed African American-Americans. Isaiah
became a farmer, and sharecropper. He started out as a young man, working on the “Hughes Overby”
Plantation in Steward County in western Georgia near the town of Omaha on the Alabama state line.
He was ten years old when the Civil War ended in April 1865. Congress declared an end to his
enslavement with the passage of the 13th Amendment in that year. Isaiah was ten years old, and
finally free in the land of his birth..
After the war, and the releasing of the slaves, Isaiah and his family elected to continue, and stayed, on
the same plantation where they had been enslaved until they finally moved on to Andersonville,
Georgia about twenty-five miles to the east in Sumter County north of Americus.. There the family
continued farming as sharecroppers on the A. B. Brown Estate. Their crops included cotton, butter
beans, sugar cane, peaches, and pecans.
They had ten (10) children living as of 1910. We have information on six children: Leanna Malinda;
Henry Madison (“Doc”); Charles (“Chum”); Maurice Monroe (“Son”); James Wesley {“Plute”); and
Arcie Lee.
We don’t know anything of Isaiah’s parents, or any siblings he had. We believe he had siblings,
however, because in the extended family was Horace, and Grover Burr who were cousins to Isaiah’s
children. Henry Madison son of Isaiah, Horace and Grover looked so much alike they were often
called “triplets,” though they were known not to be siblings at all. It seems clear Isaiah Chester had at
least two sisters since Grover and Horace were not brothers. Further, Isaiah’s siblings were likely
sisters since neither Grover, nor Horace carried the family name of Chester.
The family migrated north one by one beginning with Maurice, the fourth child. He brought with him
his wife, Beulah (“Kudda”) and their two daughters, Alma and Ruby. They moved to the Manchester
Area of the north side of Pittsburgh, in Allegheny County Pennsylvania.
The exact order of the family’s migration north is not certain. Maurice Monroe “Son” is believed to
have been the first. However, those who came first sent back for the others. For a while, Isaiah and
his two youngest children, Arcie Lee and James Wesley, lived with Henry his second-born, and his
wife Bertha Cunningham Chester in a section of north side called Woods Run in an area called “The
Pocket.”
Isaiah died in Pittsburgh in 1939 at the age of 84. There is no information on Penny Bryant Chester
after Sumter County, Georgia. Isaiah is remembered as a quiet man with a deep love of music and
enjoyed spending time harmonizing old hymns with his sons. Penny is remembered as being a small
beautiful woman with long black hair, who wore a size 2 dress, and had very small feet. She is best
remembered for her mild and gentle personality, and quiet disposition.