The children of J.D. and Anna Oliver--James II, Gertrude, Joseph, Jr., and Susan Catherine--had grown up in Copshaholm surrounded by the security of wealth. They were well-educated and well-instructed in Oliver family traditions. Of the four children, the oldest and youngest were to deviate most from the Oliver norm.
James II, born November 3, 1885,
was active and adventurous as a boy and retained those
characteristics as an adult. He attended Michigan Military
Academy and Preparatory School at Notre Dame, graduating
from Phillips Academy in Massachusetts in 1908. He was
elected a director of the Oliver Chilled Plow Works
in 1908 at the age of 22 and held various other positions
with the firm. On August 16, 1920, he married Louise Potter
Yarrington of Richmond, Virginia, the daughter of an
industrialist whom he had known for eight years. James and
Louise had no children and remained free for lengthy trips
to Europe, where he indulged "in his passion for
spending money and purchasing paintings," according to
one report from that era.
Gertrude, the second Oliver child,
was delicate, thoughtful, considerate and sensitive,
qualities similar to those of her mother. She was destined
to become the 
only child to provide grandchildren for J.D. and Anna.
Gertrude attended private school in South Bend and later
Mrs. Davis’ Finishing School at Briarcliff Manor at
Briarcliff-on-the-Hudson, New York. She was considered
pretty, was popular in her social set, and frequently
entertained at Copshaholm, where she met Charles Frederick
Cunningham of Patterson, New Jersey. Charles was a graduate
of Stevens Institute of Technology. They were married
September 30, 1916, in First Presbyterian Church, South
Bend. Charles, who later played a major role in Oliver
family affairs, was appointed secretary of the operating
committee for general management of the Oliver Chilled Plow
Works. In 1920, Gertrude was
named a director of the company, a post she held until the
company’s dissolution in 1929. The Cunninghams had three
children--Joseph Oliver, Ann Gertrude, and Fredrika
Jane--all of whom were to carry on the Oliver family
tradition of service to the South Bend community.
Joseph Doty Oliver, Jr., the third
child of J.D. and Anna Gertrude, was born on January 14,
1892. Quiet and studious, he graduated from South Bend High
School and the University of Chicago, where he earned a
bachelor of science degree. A month before his 21st
birthday, he was elected treasurer of the Oliver Chilled 
Plow Works and held that post as well as a directorship
until the company was dissolved in 1929. He apparently
inherited his father’s ability to handle large financial
investments and, undoubtedly, was his father’s favorite
son. After the Oliver company was dissolved, Joseph, Jr.
took over management of the many trusts his father had
established, and after the death of his father in 1933, he
assumed total management of the family’s financial
affairs. In 1917, he married Ellinor McMillan of Nashville,
Tennessee. She was the daughter of one of the south’s
best-known Democrats and one who had held numerous
high-ranking offices in the U.S. government. She died in
1919 of injuries suffered when thrown from a horse. After
his father’s death, Joseph Jr. moved into Copshaholm where
he resided with his sister, Susan Catherine. In later life,
he became a virtual recluse, living in a small apartment on
the third floor of Copshaholm. He died on July 6, 1972, at
the age of 80.
The fourth Oliver child was Susan
Catherine, who was born March 6, 1896. She
graduated from South Bend High School in 1914, attended the
Finishing School of Mrs. Davis at Briarcliff-on-the-Hudson,
and received a degree from Finch College in New York in
1916. Catherine never married. She served in the Red Cross
during World War I and also carried on a number of
intellectual and physical pursuits, among them, golf, at
which she excelled. She reportedly was a good friend of the
well-known golf professional Chick Evans. Catherine became a
symbol of the liberated woman of the 1920s. There were
rounds of parties at Copshaholm, entertainment for as many
as 600 guests at South Bend’s Palais Royale Ballroom, and
lengthy foreign cruises. Though she served as a member of
the board of directors of the Oliver company, Catherine took
no part in company management.
After the death of her parents, Catherine, like Joseph, lived out her life in Copshaholm: he, in his third floor apartment and she, in a suite of rooms on the second floor. Mostly, they saw each other only at dinner. She died April 19, 1970.
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